TY  - JOUR
AU  - Milovanović, Milan R.
AU  - Živković, Jelena M.
AU  - Ninković, Dragan
AU  - Zarić, Snežana D.
PY  - 2023
UR  - http://cherry.chem.bg.ac.rs/handle/123456789/6281
AB  - Antiparallel water-water interaction is a significant interaction between two water molecules and plays an important role in liquid water. The potential energy surface of antiparallel water-water interaction was calculated at accurate CCSD(T)/CBS level of theory by systematic changes of the torsion angle THOHO, parallel displacement r, normal distance R, and water-water dihedral angle Pa/Pb. The results show that the most stable geometry of antiparallel water-water interaction has an interaction energy of −4.22 kcal/mol and THOHO = 140°. A significant portion of the antiparallel interactions have interaction energies more negative than −2.0 kcal/mol. The angle α of the most stable geometries of antiparallel water-water interactions is in the range 110°–120°. Comparison with classical hydrogen bonds in water dimers shows that hydrogen bonds with values of angle α < 140° have interaction energies up to −3.2 kcal/mol, while a significant number of antiparallel water-water interactions is stronger than it. The antiparallel geometry is a low barrier transition state between two hydrogen bonded minima with changed acceptor–donor roles of two water molecules.
PB  - Elsevier
T2  - Journal of Molecular Liquids
T1  - Potential energy surfaces of antiparallel water-water interactions
VL  - 389
SP  - 122758
DO  - 10.1016/j.molliq.2023.122758
ER  - 

@article{
author = "Milovanović, Milan R. and Živković, Jelena M. and Ninković, Dragan and Zarić, Snežana D.",
year = "2023",
abstract = "Antiparallel water-water interaction is a significant interaction between two water molecules and plays an important role in liquid water. The potential energy surface of antiparallel water-water interaction was calculated at accurate CCSD(T)/CBS level of theory by systematic changes of the torsion angle THOHO, parallel displacement r, normal distance R, and water-water dihedral angle Pa/Pb. The results show that the most stable geometry of antiparallel water-water interaction has an interaction energy of −4.22 kcal/mol and THOHO = 140°. A significant portion of the antiparallel interactions have interaction energies more negative than −2.0 kcal/mol. The angle α of the most stable geometries of antiparallel water-water interactions is in the range 110°–120°. Comparison with classical hydrogen bonds in water dimers shows that hydrogen bonds with values of angle α < 140° have interaction energies up to −3.2 kcal/mol, while a significant number of antiparallel water-water interactions is stronger than it. The antiparallel geometry is a low barrier transition state between two hydrogen bonded minima with changed acceptor–donor roles of two water molecules.",
publisher = "Elsevier",
journal = "Journal of Molecular Liquids",
title = "Potential energy surfaces of antiparallel water-water interactions",
volume = "389",
pages = "122758",
doi = "10.1016/j.molliq.2023.122758"
}

Milovanović, M. R., Živković, J. M., Ninković, D.,& Zarić, S. D.. (2023). Potential energy surfaces of antiparallel water-water interactions. in Journal of Molecular Liquids
Elsevier., 389, 122758.
https://doi.org/10.1016/j.molliq.2023.122758

Milovanović MR, Živković JM, Ninković D, Zarić SD. Potential energy surfaces of antiparallel water-water interactions. in Journal of Molecular Liquids. 2023;389:122758.
doi:10.1016/j.molliq.2023.122758 .

Milovanović, Milan R., Živković, Jelena M., Ninković, Dragan, Zarić, Snežana D., "Potential energy surfaces of antiparallel water-water interactions" in Journal of Molecular Liquids, 389 (2023):122758,
https://doi.org/10.1016/j.molliq.2023.122758 . .

TY  - CONF
AU  - Milovanović, Milan R.
AU  - Živković, Jelena M.
AU  - Ninković, Dragan B.
AU  - Blagojević, Jelena P.
AU  - Zarić, Snežana D.
PY  - 2023
UR  - www.iccbikg2023.kg.ac.rs
UR  - http://cherry.chem.bg.ac.rs/handle/123456789/6342
AB  - Considering the properties of water and benzene molecules, one can expect very different benzene/benzene and water/water interactions. Benzene does not have a dipole moment, while water does. Analysis of the data in the crystal structures in the Cambridge Structural Database (CSD) revealed the most frequent benzene/benzene and water/water geometries. The majority of the benzene/benzene interactions in the crystal structures in the CSD are stacking interactions with large horizontal displacements, and not geometries that are minima on benzene/benzene potential surface. A large number of the water/water contacts in the CSD are hydrogen bonds, 70% of all attractive water/water interactions. In addition, water/water contacts with two water forming antiparallel interactions are 20% of all attractive water/water contacts. In these contacts, the O-H bonds of water molecules are in antiparallel orientation. In benzene/benzene interactions at large horizontal displacements, two C-H bonds also are in the antiparallel orientation. This shows that although the two molecules are different, both of them form antiparallel interactions with a local O-H and C-H dipole moments.
C3  - 2nd International Conference on Chemo and Bioinformatics (ICCBIKG_2023), Book of Proceedings, 28-29 September 2023, Kragujevac, Serbia
T1  - Benzene and water – different or similar?
UR  - https://hdl.handle.net/21.15107/rcub_cherry_6342
ER  - 

@conference{
author = "Milovanović, Milan R. and Živković, Jelena M. and Ninković, Dragan B. and Blagojević, Jelena P. and Zarić, Snežana D.",
year = "2023",
abstract = "Considering the properties of water and benzene molecules, one can expect very different benzene/benzene and water/water interactions. Benzene does not have a dipole moment, while water does. Analysis of the data in the crystal structures in the Cambridge Structural Database (CSD) revealed the most frequent benzene/benzene and water/water geometries. The majority of the benzene/benzene interactions in the crystal structures in the CSD are stacking interactions with large horizontal displacements, and not geometries that are minima on benzene/benzene potential surface. A large number of the water/water contacts in the CSD are hydrogen bonds, 70% of all attractive water/water interactions. In addition, water/water contacts with two water forming antiparallel interactions are 20% of all attractive water/water contacts. In these contacts, the O-H bonds of water molecules are in antiparallel orientation. In benzene/benzene interactions at large horizontal displacements, two C-H bonds also are in the antiparallel orientation. This shows that although the two molecules are different, both of them form antiparallel interactions with a local O-H and C-H dipole moments.",
journal = "2nd International Conference on Chemo and Bioinformatics (ICCBIKG_2023), Book of Proceedings, 28-29 September 2023, Kragujevac, Serbia",
title = "Benzene and water – different or similar?",
url = "https://hdl.handle.net/21.15107/rcub_cherry_6342"
}

Milovanović, M. R., Živković, J. M., Ninković, D. B., Blagojević, J. P.,& Zarić, S. D.. (2023). Benzene and water – different or similar?. in 2nd International Conference on Chemo and Bioinformatics (ICCBIKG_2023), Book of Proceedings, 28-29 September 2023, Kragujevac, Serbia.
https://hdl.handle.net/21.15107/rcub_cherry_6342

Milovanović MR, Živković JM, Ninković DB, Blagojević JP, Zarić SD. Benzene and water – different or similar?. in 2nd International Conference on Chemo and Bioinformatics (ICCBIKG_2023), Book of Proceedings, 28-29 September 2023, Kragujevac, Serbia. 2023;.
https://hdl.handle.net/21.15107/rcub_cherry_6342 .

Milovanović, Milan R., Živković, Jelena M., Ninković, Dragan B., Blagojević, Jelena P., Zarić, Snežana D., "Benzene and water – different or similar?" in 2nd International Conference on Chemo and Bioinformatics (ICCBIKG_2023), Book of Proceedings, 28-29 September 2023, Kragujevac, Serbia (2023),
https://hdl.handle.net/21.15107/rcub_cherry_6342 .

TY  - CONF
AU  - Milovanović, Milan R.
AU  - Živković, Jelena M.
AU  - Stanković, Ivana M.
AU  - Ninković, Dragan B.
AU  - Zarić, Snežana D.
PY  - 2023
UR  - www.iccbikg2023.kg.ac.rs
UR  - http://cherry.chem.bg.ac.rs/handle/123456789/6346
AB  - Water is one of the most important molecules on the Earth. Since water plays a crucial role in many life processes, it is of great importance to understand every aspect of its behavior and interactions with itself and its surroundings. It is known that water molecules can interact via classical hydrogen bonds and antiparallel interactions, with interaction energies of - 5.02 kcal/mol and -4.22 kcal/mol, respectively. Besides these attractive interactions, repulsive interactions were also noticed. In this work, we analyzed repulsive water-water contacts from the Cambridge Structural Database. All interaction energies were calculated at the so- called gold standard, i.e., CCSD(T)/CBS level of theory. It was found that among all water-water contacts, ca. 20% (2035 contacts) are repulsive with interaction energies mainly up to 2 kcal/mol. Most of these repulsive contacts do not belong to two main groups of water-water contacts. Namely, 12.8% of all repulsive contacts can be classified as classical hydrogen bonds, 2.1% to the antiparallel interactions, and the rest (85.3%) as remaining contacts. This study points out that additional attention should be paid when one deals with contacts including water or, eventually, hydrogen atoms in general.
C3  - 2nd International Conference on Chemo and Bioinformatics (ICCBIKG_2023), Book of Proceedings, 28-29 September 2023, Kragujevac, Serbia, 2023
T1  - Repulsive water-water contacts from Cambridge Structural Database
SP  - 637
EP  - 640
UR  - https://hdl.handle.net/21.15107/rcub_cherry_6346
ER  - 

@conference{
author = "Milovanović, Milan R. and Živković, Jelena M. and Stanković, Ivana M. and Ninković, Dragan B. and Zarić, Snežana D.",
year = "2023",
abstract = "Water is one of the most important molecules on the Earth. Since water plays a crucial role in many life processes, it is of great importance to understand every aspect of its behavior and interactions with itself and its surroundings. It is known that water molecules can interact via classical hydrogen bonds and antiparallel interactions, with interaction energies of - 5.02 kcal/mol and -4.22 kcal/mol, respectively. Besides these attractive interactions, repulsive interactions were also noticed. In this work, we analyzed repulsive water-water contacts from the Cambridge Structural Database. All interaction energies were calculated at the so- called gold standard, i.e., CCSD(T)/CBS level of theory. It was found that among all water-water contacts, ca. 20% (2035 contacts) are repulsive with interaction energies mainly up to 2 kcal/mol. Most of these repulsive contacts do not belong to two main groups of water-water contacts. Namely, 12.8% of all repulsive contacts can be classified as classical hydrogen bonds, 2.1% to the antiparallel interactions, and the rest (85.3%) as remaining contacts. This study points out that additional attention should be paid when one deals with contacts including water or, eventually, hydrogen atoms in general.",
journal = "2nd International Conference on Chemo and Bioinformatics (ICCBIKG_2023), Book of Proceedings, 28-29 September 2023, Kragujevac, Serbia, 2023",
title = "Repulsive water-water contacts from Cambridge Structural Database",
pages = "637-640",
url = "https://hdl.handle.net/21.15107/rcub_cherry_6346"
}

Milovanović, M. R., Živković, J. M., Stanković, I. M., Ninković, D. B.,& Zarić, S. D.. (2023). Repulsive water-water contacts from Cambridge Structural Database. in 2nd International Conference on Chemo and Bioinformatics (ICCBIKG_2023), Book of Proceedings, 28-29 September 2023, Kragujevac, Serbia, 2023, 637-640.
https://hdl.handle.net/21.15107/rcub_cherry_6346

Milovanović MR, Živković JM, Stanković IM, Ninković DB, Zarić SD. Repulsive water-water contacts from Cambridge Structural Database. in 2nd International Conference on Chemo and Bioinformatics (ICCBIKG_2023), Book of Proceedings, 28-29 September 2023, Kragujevac, Serbia, 2023. 2023;:637-640.
https://hdl.handle.net/21.15107/rcub_cherry_6346 .

Milovanović, Milan R., Živković, Jelena M., Stanković, Ivana M., Ninković, Dragan B., Zarić, Snežana D., "Repulsive water-water contacts from Cambridge Structural Database" in 2nd International Conference on Chemo and Bioinformatics (ICCBIKG_2023), Book of Proceedings, 28-29 September 2023, Kragujevac, Serbia, 2023 (2023):637-640,
https://hdl.handle.net/21.15107/rcub_cherry_6346 .

TY  - CONF
AU  - Milovanović, Milan R.
AU  - Živković, Jelena M.
AU  - Ninković, Dragan B.
AU  - Blagojević, Jelena P.
AU  - Zarić, Snežana D.
PY  - 2023
UR  - https://physics.mff.cuni.cz/kchfo/MIB23
UR  - http://cherry.chem.bg.ac.rs/handle/123456789/6350
AB  - Considering properties of water and benzene molecules, one can expect very different benzene/benzene and water/water interactions. Benzene does not have a dipole moment, while water has. Quantum chemical calculations showed that minima on potential surface of water/water interactions is hydrogen bond, where dipole moment of water plays important role. The calculations show that the minima on potential surface for benzene/benzene interactions are stacking (parallel displaced) geometry and T-shaped geometry. Analysis of the data in the crystal structures in the Cambridge Structural Database (CSD) revealed the most frequent benzene/benzene and water/water geometries. Majority of the benzene/benzene interactions in the crystal structures in the CSD are tacking interactions with large horizontal displacements, and not geometries that are minima on benzene/benzene potential surface. Large number of the water/water contacts in the CSD are hydrogen bonds, 70% of all attractive water/water interactions. In addition water/water contacts with two water forming antiparallel interactions are 20% of all attractive water/water contacts. In these contacts O-H bonds of water molecules are in antiparallel orientation (Fig. 1). In benzene/benzene interactions at large horizontal displacements two C-H bonds also are in the antiparallel orientation (Fig. 1).
C3  - Modeling Interactions in Biomolecules IX, Book of Abstracts, Pruhonice, Prague-Pruhonice, Czech Republic, 10th-14th September 2023
T1  - Differences and Similarities in Benzene/Benzene and Water/Water Interactions
SP  - 56
EP  - 56
UR  - https://hdl.handle.net/21.15107/rcub_cherry_6350
ER  - 

@conference{
author = "Milovanović, Milan R. and Živković, Jelena M. and Ninković, Dragan B. and Blagojević, Jelena P. and Zarić, Snežana D.",
year = "2023",
abstract = "Considering properties of water and benzene molecules, one can expect very different benzene/benzene and water/water interactions. Benzene does not have a dipole moment, while water has. Quantum chemical calculations showed that minima on potential surface of water/water interactions is hydrogen bond, where dipole moment of water plays important role. The calculations show that the minima on potential surface for benzene/benzene interactions are stacking (parallel displaced) geometry and T-shaped geometry. Analysis of the data in the crystal structures in the Cambridge Structural Database (CSD) revealed the most frequent benzene/benzene and water/water geometries. Majority of the benzene/benzene interactions in the crystal structures in the CSD are tacking interactions with large horizontal displacements, and not geometries that are minima on benzene/benzene potential surface. Large number of the water/water contacts in the CSD are hydrogen bonds, 70% of all attractive water/water interactions. In addition water/water contacts with two water forming antiparallel interactions are 20% of all attractive water/water contacts. In these contacts O-H bonds of water molecules are in antiparallel orientation (Fig. 1). In benzene/benzene interactions at large horizontal displacements two C-H bonds also are in the antiparallel orientation (Fig. 1).",
journal = "Modeling Interactions in Biomolecules IX, Book of Abstracts, Pruhonice, Prague-Pruhonice, Czech Republic, 10th-14th September 2023",
title = "Differences and Similarities in Benzene/Benzene and Water/Water Interactions",
pages = "56-56",
url = "https://hdl.handle.net/21.15107/rcub_cherry_6350"
}

Milovanović, M. R., Živković, J. M., Ninković, D. B., Blagojević, J. P.,& Zarić, S. D.. (2023). Differences and Similarities in Benzene/Benzene and Water/Water Interactions. in Modeling Interactions in Biomolecules IX, Book of Abstracts, Pruhonice, Prague-Pruhonice, Czech Republic, 10th-14th September 2023, 56-56.
https://hdl.handle.net/21.15107/rcub_cherry_6350

Milovanović MR, Živković JM, Ninković DB, Blagojević JP, Zarić SD. Differences and Similarities in Benzene/Benzene and Water/Water Interactions. in Modeling Interactions in Biomolecules IX, Book of Abstracts, Pruhonice, Prague-Pruhonice, Czech Republic, 10th-14th September 2023. 2023;:56-56.
https://hdl.handle.net/21.15107/rcub_cherry_6350 .

Milovanović, Milan R., Živković, Jelena M., Ninković, Dragan B., Blagojević, Jelena P., Zarić, Snežana D., "Differences and Similarities in Benzene/Benzene and Water/Water Interactions" in Modeling Interactions in Biomolecules IX, Book of Abstracts, Pruhonice, Prague-Pruhonice, Czech Republic, 10th-14th September 2023 (2023):56-56,
https://hdl.handle.net/21.15107/rcub_cherry_6350 .

TY  - CONF
AU  - Milovanović, Milan R.
AU  - Živković, Jelena M.
AU  - Ninković, Dragan B.
AU  - Blagojević, Jelena P.
AU  - Zarić, Snežana D.
PY  - 2023
UR  - http://cherry.chem.bg.ac.rs/handle/123456789/6371
AB  - In spite of being quite different substances, benzene and water can form similar noncovalent interactions. Analysis of the
data in the crystal structures in the Cambridge Structural Database (CSD) revealed similarities in benzene/benzene and
water/water interactions, since both benzene/benzene and water/water can form antiparallel interactions.
The quantum chemical calculations of potential surface of water/water interactions showed that the minimum is hydrogen
bond. Analysis of the data in the crystal structures in the Cambridge Structural Database (CSD) revealed antiparallel
water/water interactions, in addition to classical hydrogen bonds (1). The geometries of all water/water contacts in the CSD
were analyzed and for all contacts interaction energies were calculated at accurate CCSD(T)/CBS level. The results
showed that the most frequent water/water contacts are hydrogen bonds; hydrogen bonds are 70% of all attractive
water/water interactions. In addition, water/water contacts with antiparallel interactions are 20% of all attractive water/water
contacts. In these contacts O-H bonds of water molecules are in antiparallel orientation (Figure).
The quantum chemical calculations of potential surface of benzene/benzene interactions showed two minima stacking
(parallel displaced) geometry and T-shaped geometry. Analysis of all benzene/benzene contacts in the crystal structures
in the CSD revealed the most frequent benzene/benzene geometries (2). Majority of the benzene/benzene interactions in
the CSD are stacking interactions with large horizontal displacements, and not geometries that are minima on
benzene/benzene potential surface. In benzene/benzene interactions at large horizontal displacements two C-H bonds are in the antiparallel orientation (Figure).
In these O-H and C-H antiparallel interactions two dipoles are in antiparallel orientation enabling close contact of positive
and negative regions of the dipoles. Symmetry Adapted Perturbation Theory (SAPT) analysis showed that electrostatic is
the largest attractive force in the antiparallel interactions. Antiparallel interactions are also possible between O-H and C-H
bonds; in the crystal structures from the CSD these interactions are observed as one of the types of water benzene interactions (3).
PB  - University of Strasbourg
C3  - The van der Waals-London Discussions, Univesity of Strasbourg, October 26-27th 2023
T1  - Antiparallel Noncovalent Interactions
UR  - https://hdl.handle.net/21.15107/rcub_cherry_6371
ER  - 

@conference{
author = "Milovanović, Milan R. and Živković, Jelena M. and Ninković, Dragan B. and Blagojević, Jelena P. and Zarić, Snežana D.",
year = "2023",
abstract = "In spite of being quite different substances, benzene and water can form similar noncovalent interactions. Analysis of the
data in the crystal structures in the Cambridge Structural Database (CSD) revealed similarities in benzene/benzene and
water/water interactions, since both benzene/benzene and water/water can form antiparallel interactions.
The quantum chemical calculations of potential surface of water/water interactions showed that the minimum is hydrogen
bond. Analysis of the data in the crystal structures in the Cambridge Structural Database (CSD) revealed antiparallel
water/water interactions, in addition to classical hydrogen bonds (1). The geometries of all water/water contacts in the CSD
were analyzed and for all contacts interaction energies were calculated at accurate CCSD(T)/CBS level. The results
showed that the most frequent water/water contacts are hydrogen bonds; hydrogen bonds are 70% of all attractive
water/water interactions. In addition, water/water contacts with antiparallel interactions are 20% of all attractive water/water
contacts. In these contacts O-H bonds of water molecules are in antiparallel orientation (Figure).
The quantum chemical calculations of potential surface of benzene/benzene interactions showed two minima stacking
(parallel displaced) geometry and T-shaped geometry. Analysis of all benzene/benzene contacts in the crystal structures
in the CSD revealed the most frequent benzene/benzene geometries (2). Majority of the benzene/benzene interactions in
the CSD are stacking interactions with large horizontal displacements, and not geometries that are minima on
benzene/benzene potential surface. In benzene/benzene interactions at large horizontal displacements two C-H bonds are in the antiparallel orientation (Figure).
In these O-H and C-H antiparallel interactions two dipoles are in antiparallel orientation enabling close contact of positive
and negative regions of the dipoles. Symmetry Adapted Perturbation Theory (SAPT) analysis showed that electrostatic is
the largest attractive force in the antiparallel interactions. Antiparallel interactions are also possible between O-H and C-H
bonds; in the crystal structures from the CSD these interactions are observed as one of the types of water benzene interactions (3).",
publisher = "University of Strasbourg",
journal = "The van der Waals-London Discussions, Univesity of Strasbourg, October 26-27th 2023",
title = "Antiparallel Noncovalent Interactions",
url = "https://hdl.handle.net/21.15107/rcub_cherry_6371"
}

Milovanović, M. R., Živković, J. M., Ninković, D. B., Blagojević, J. P.,& Zarić, S. D.. (2023). Antiparallel Noncovalent Interactions. in The van der Waals-London Discussions, Univesity of Strasbourg, October 26-27th 2023
University of Strasbourg..
https://hdl.handle.net/21.15107/rcub_cherry_6371

Milovanović MR, Živković JM, Ninković DB, Blagojević JP, Zarić SD. Antiparallel Noncovalent Interactions. in The van der Waals-London Discussions, Univesity of Strasbourg, October 26-27th 2023. 2023;.
https://hdl.handle.net/21.15107/rcub_cherry_6371 .

Milovanović, Milan R., Živković, Jelena M., Ninković, Dragan B., Blagojević, Jelena P., Zarić, Snežana D., "Antiparallel Noncovalent Interactions" in The van der Waals-London Discussions, Univesity of Strasbourg, October 26-27th 2023 (2023),
https://hdl.handle.net/21.15107/rcub_cherry_6371 .

TY  - CONF
AU  - Zarić, Snežana D.
AU  - Milovanović, Milan R.
AU  - Stanković, Ivana M.
AU  - Živković, Jelena M.
AU  - Ninković, Dragan B.
AU  - Hall, Michael B.
PY  - 2023
UR  - http://cherry.chem.bg.ac.rs/handle/123456789/6372
AB  - Water is one of the most important molecules; it is clear that life on Earth depends on its anomalous properties derived from its unique structure: small size and high polarity [1] as well as flexibility [2]. A fundamental ability of water is hydrogen bonding.
Hydrogen bonds are generally considered strong when the H···Y distance is 2.2 to 2.5 Å and the X—H···Y angle is 170 to 180⁰, whereas for weak hydrogen-bond interactions, the H···Y distance is larger than 3.2 Å and the bond angle is less than 130⁰. Between strong and weak interactions are those ones of the moderate strength [3].
In this work [4], we analyzed geometries of all water–water interactions in the Cambridge Structural Database (CSD). We found 9928 water-water contacts and for all of them we calculated interaction energies at the accurate CCSD(T)/CBS level. Our results indicate two types of attractive water–water interactions; the first type involves the classical hydrogen bonds (dOH < 3.0 Å and α > 120⁰), whereas the second type involves antiparallel O—H bond interactions (Figure 1). Namely, c.a. 70% of attractive water–water contacts are classical hydrogen bonds with most being stronger than -3.3 kcal/mol, while c.a. 19% of attractive water–water contacts are antiparallel dipolar interactions with interaction energies up to -4.7 kcal/mol.
C3  - 17th International Congress of Quantum Chemistry (17thICQC), Book of abstracts, June 26 – July 1 2023, Bratislava, Slovakia
T1  - Antiparallel interactions as a mode of hydrogen bonding: Case of water in solid state
UR  - https://hdl.handle.net/21.15107/rcub_cherry_6372
ER  - 

@conference{
author = "Zarić, Snežana D. and Milovanović, Milan R. and Stanković, Ivana M. and Živković, Jelena M. and Ninković, Dragan B. and Hall, Michael B.",
year = "2023",
abstract = "Water is one of the most important molecules; it is clear that life on Earth depends on its anomalous properties derived from its unique structure: small size and high polarity [1] as well as flexibility [2]. A fundamental ability of water is hydrogen bonding.
Hydrogen bonds are generally considered strong when the H···Y distance is 2.2 to 2.5 Å and the X—H···Y angle is 170 to 180⁰, whereas for weak hydrogen-bond interactions, the H···Y distance is larger than 3.2 Å and the bond angle is less than 130⁰. Between strong and weak interactions are those ones of the moderate strength [3].
In this work [4], we analyzed geometries of all water–water interactions in the Cambridge Structural Database (CSD). We found 9928 water-water contacts and for all of them we calculated interaction energies at the accurate CCSD(T)/CBS level. Our results indicate two types of attractive water–water interactions; the first type involves the classical hydrogen bonds (dOH < 3.0 Å and α > 120⁰), whereas the second type involves antiparallel O—H bond interactions (Figure 1). Namely, c.a. 70% of attractive water–water contacts are classical hydrogen bonds with most being stronger than -3.3 kcal/mol, while c.a. 19% of attractive water–water contacts are antiparallel dipolar interactions with interaction energies up to -4.7 kcal/mol.",
journal = "17th International Congress of Quantum Chemistry (17thICQC), Book of abstracts, June 26 – July 1 2023, Bratislava, Slovakia",
title = "Antiparallel interactions as a mode of hydrogen bonding: Case of water in solid state",
url = "https://hdl.handle.net/21.15107/rcub_cherry_6372"
}

Zarić, S. D., Milovanović, M. R., Stanković, I. M., Živković, J. M., Ninković, D. B.,& Hall, M. B.. (2023). Antiparallel interactions as a mode of hydrogen bonding: Case of water in solid state. in 17th International Congress of Quantum Chemistry (17thICQC), Book of abstracts, June 26 – July 1 2023, Bratislava, Slovakia.
https://hdl.handle.net/21.15107/rcub_cherry_6372

Zarić SD, Milovanović MR, Stanković IM, Živković JM, Ninković DB, Hall MB. Antiparallel interactions as a mode of hydrogen bonding: Case of water in solid state. in 17th International Congress of Quantum Chemistry (17thICQC), Book of abstracts, June 26 – July 1 2023, Bratislava, Slovakia. 2023;.
https://hdl.handle.net/21.15107/rcub_cherry_6372 .

Zarić, Snežana D., Milovanović, Milan R., Stanković, Ivana M., Živković, Jelena M., Ninković, Dragan B., Hall, Michael B., "Antiparallel interactions as a mode of hydrogen bonding: Case of water in solid state" in 17th International Congress of Quantum Chemistry (17thICQC), Book of abstracts, June 26 – July 1 2023, Bratislava, Slovakia (2023),
https://hdl.handle.net/21.15107/rcub_cherry_6372 .

TY  - CONF
AU  - Živković, Jelena M.
AU  - Milovanović, Milan R.
AU  - Zarić, Snežana D.
PY  - 2022
UR  - http://cherry.chem.bg.ac.rs/handle/123456789/6352
AB  - Hydrogen bonds stabilize crystal packing of small molecules, structures of proteins, and geometries of coordination compounds.[1] Hydrogen bonds of coordinated ethylenediamine (en) play important roles in catalytic activity.[2] In this work,[3] geometrical parameters and strength of these interactions were studied. The Cambridge Structural Database (CSD) was searched to find crystal structures that contain at least one coordinated en to a transition metal, and at least one free water molecule interacting with en via NH...O hydrogen bond. All quantum chemical computations were performed at M06L-GD3/def2-TZVPP/BSSE level. The maximum of dOH (Figure 1) distribution is at 2.0 Å - 2.1 Å, while α (Figure 1) distribution revealed the maximum at 150⁰ - 160. These geometric parameters are correlated, i.e. larger angles correspond to shorter distances. Most abundant en complexes are those that contain cobalt. Most of complexes are in octahedral geometry. The interaction energies for neutral metal complexes are up to of  -6.7 kcal/mol. An increase of charge of complexes causes an increase in the energy of hydrogen bond. Namely, for singly charged metal complexes interaction energies are in range from -8.5 to -11.8 kcal/mol. Interaction energies of doubly charged metal complexes span from -15.6 kcal/mol to -19.9 kcal/mol. Triply charged complex has the strongest interaction energies, up to -28.0 kcal/mol.[3] In addition, a good correlation between the energies of hydrogen bond and electrostatic potential on interacting hydrogen atom is observed.
PB  - University of Strasbourg and the Centre National de la Recherche Scientifique
C3  - 2nd International Conferences on Noncovalent Interactions (ICNI2022), Book of abstracts, 18-22 July, 2022, Strasbourg, France
T1  - Hydrogen bonds of coordinated ethylenediamine and water
UR  - https://hdl.handle.net/21.15107/rcub_cherry_6352
ER  - 

@conference{
author = "Živković, Jelena M. and Milovanović, Milan R. and Zarić, Snežana D.",
year = "2022",
abstract = "Hydrogen bonds stabilize crystal packing of small molecules, structures of proteins, and geometries of coordination compounds.[1] Hydrogen bonds of coordinated ethylenediamine (en) play important roles in catalytic activity.[2] In this work,[3] geometrical parameters and strength of these interactions were studied. The Cambridge Structural Database (CSD) was searched to find crystal structures that contain at least one coordinated en to a transition metal, and at least one free water molecule interacting with en via NH...O hydrogen bond. All quantum chemical computations were performed at M06L-GD3/def2-TZVPP/BSSE level. The maximum of dOH (Figure 1) distribution is at 2.0 Å - 2.1 Å, while α (Figure 1) distribution revealed the maximum at 150⁰ - 160. These geometric parameters are correlated, i.e. larger angles correspond to shorter distances. Most abundant en complexes are those that contain cobalt. Most of complexes are in octahedral geometry. The interaction energies for neutral metal complexes are up to of  -6.7 kcal/mol. An increase of charge of complexes causes an increase in the energy of hydrogen bond. Namely, for singly charged metal complexes interaction energies are in range from -8.5 to -11.8 kcal/mol. Interaction energies of doubly charged metal complexes span from -15.6 kcal/mol to -19.9 kcal/mol. Triply charged complex has the strongest interaction energies, up to -28.0 kcal/mol.[3] In addition, a good correlation between the energies of hydrogen bond and electrostatic potential on interacting hydrogen atom is observed.",
publisher = "University of Strasbourg and the Centre National de la Recherche Scientifique",
journal = "2nd International Conferences on Noncovalent Interactions (ICNI2022), Book of abstracts, 18-22 July, 2022, Strasbourg, France",
title = "Hydrogen bonds of coordinated ethylenediamine and water",
url = "https://hdl.handle.net/21.15107/rcub_cherry_6352"
}

Živković, J. M., Milovanović, M. R.,& Zarić, S. D.. (2022). Hydrogen bonds of coordinated ethylenediamine and water. in 2nd International Conferences on Noncovalent Interactions (ICNI2022), Book of abstracts, 18-22 July, 2022, Strasbourg, France
University of Strasbourg and the Centre National de la Recherche Scientifique..
https://hdl.handle.net/21.15107/rcub_cherry_6352

Živković JM, Milovanović MR, Zarić SD. Hydrogen bonds of coordinated ethylenediamine and water. in 2nd International Conferences on Noncovalent Interactions (ICNI2022), Book of abstracts, 18-22 July, 2022, Strasbourg, France. 2022;.
https://hdl.handle.net/21.15107/rcub_cherry_6352 .

Živković, Jelena M., Milovanović, Milan R., Zarić, Snežana D., "Hydrogen bonds of coordinated ethylenediamine and water" in 2nd International Conferences on Noncovalent Interactions (ICNI2022), Book of abstracts, 18-22 July, 2022, Strasbourg, France (2022),
https://hdl.handle.net/21.15107/rcub_cherry_6352 .

TY  - CONF
AU  - Milovanović, Milan R.
PY  - 2022
UR  - https://wp.nyu.edu/abudhabi-iccoss2021
UR  - http://cherry.chem.bg.ac.rs/handle/123456789/6354
AB  - The hydrogen bonds of coordinated ethylenediamine (en) play important roles in catalytic activity [1], the aim of this work was to study geometrical parameters and strength of these interactions. The search of crystal structures archived in Cambridge Structural Database (CSD) was performed in order to find crystal structures containing at least one coordinated en to a transition metal, and at least one free water molecule interacting with en via NH···O hydrogen bond. All calculations were performed at M06L-GD3/def2-TZVPP/BSSE level of theory since it was confirmed that this level gives a good agreement with the CCSD(T)/CBS level. The distribution of dOH (Fig. 1) showed the maximum is at 2.0 Å - 2.1 Å, with a relatively large number of structures with distances shorter than 2.0 Å. The distribution of α (Fig 1.) revealed the maximum at 150⁰ - 160. The dOH and α are correlated, i.e. shorter distances correspond to larger angles. Most of en complexes contain cobalt, followed with palladium, nickel, and copper and most of them are in octahedral geometry. The coordination of en to the metal ions strengthens its hydrogen bonds with a water molecule. Namely, the energy of hydrogen bond of noncoordianted ethylenediamine is -2.3 kcal/mol, while the interaction energies for neutral metal complexes are in the range of -4.0 kcal/mol to -6.7 kcal/mol. Increasing of charge of complexes increases the energy of hydrogen bond. For singly charged complexes energy spans from -8.5 to -11.8 kcal/mol; for doubly charged complexes it spans from -15.6 kcal/mol to -19.9 kcal/mol; while triply charged complex has the strongest interaction of -28.0 kcal/mol [2]. In addition, the energies of hydrogen bond have a good correlation with the electrostatic potential on interacting hydrogen atom.
C3  - 25th International Conference on the Chemistry of the Organic Solid State (ICCOSS XXV), Book of abstracts, July 3 8, 2022, Ohrid, Macedonia
T1  - Joint Crystal Structure and Computational Study of Hydrogen Bonds of Ethylenediamine
SP  - 121
EP  - 121
UR  - https://hdl.handle.net/21.15107/rcub_cherry_6354
ER  - 

@conference{
author = "Milovanović, Milan R.",
year = "2022",
abstract = "The hydrogen bonds of coordinated ethylenediamine (en) play important roles in catalytic activity [1], the aim of this work was to study geometrical parameters and strength of these interactions. The search of crystal structures archived in Cambridge Structural Database (CSD) was performed in order to find crystal structures containing at least one coordinated en to a transition metal, and at least one free water molecule interacting with en via NH···O hydrogen bond. All calculations were performed at M06L-GD3/def2-TZVPP/BSSE level of theory since it was confirmed that this level gives a good agreement with the CCSD(T)/CBS level. The distribution of dOH (Fig. 1) showed the maximum is at 2.0 Å - 2.1 Å, with a relatively large number of structures with distances shorter than 2.0 Å. The distribution of α (Fig 1.) revealed the maximum at 150⁰ - 160. The dOH and α are correlated, i.e. shorter distances correspond to larger angles. Most of en complexes contain cobalt, followed with palladium, nickel, and copper and most of them are in octahedral geometry. The coordination of en to the metal ions strengthens its hydrogen bonds with a water molecule. Namely, the energy of hydrogen bond of noncoordianted ethylenediamine is -2.3 kcal/mol, while the interaction energies for neutral metal complexes are in the range of -4.0 kcal/mol to -6.7 kcal/mol. Increasing of charge of complexes increases the energy of hydrogen bond. For singly charged complexes energy spans from -8.5 to -11.8 kcal/mol; for doubly charged complexes it spans from -15.6 kcal/mol to -19.9 kcal/mol; while triply charged complex has the strongest interaction of -28.0 kcal/mol [2]. In addition, the energies of hydrogen bond have a good correlation with the electrostatic potential on interacting hydrogen atom.",
journal = "25th International Conference on the Chemistry of the Organic Solid State (ICCOSS XXV), Book of abstracts, July 3 8, 2022, Ohrid, Macedonia",
title = "Joint Crystal Structure and Computational Study of Hydrogen Bonds of Ethylenediamine",
pages = "121-121",
url = "https://hdl.handle.net/21.15107/rcub_cherry_6354"
}

Milovanović, M. R.. (2022). Joint Crystal Structure and Computational Study of Hydrogen Bonds of Ethylenediamine. in 25th International Conference on the Chemistry of the Organic Solid State (ICCOSS XXV), Book of abstracts, July 3 8, 2022, Ohrid, Macedonia, 121-121.
https://hdl.handle.net/21.15107/rcub_cherry_6354

Milovanović MR. Joint Crystal Structure and Computational Study of Hydrogen Bonds of Ethylenediamine. in 25th International Conference on the Chemistry of the Organic Solid State (ICCOSS XXV), Book of abstracts, July 3 8, 2022, Ohrid, Macedonia. 2022;:121-121.
https://hdl.handle.net/21.15107/rcub_cherry_6354 .

Milovanović, Milan R., "Joint Crystal Structure and Computational Study of Hydrogen Bonds of Ethylenediamine" in 25th International Conference on the Chemistry of the Organic Solid State (ICCOSS XXV), Book of abstracts, July 3 8, 2022, Ohrid, Macedonia (2022):121-121,
https://hdl.handle.net/21.15107/rcub_cherry_6354 .

TY  - JOUR
AU  - Živković, Jelena M.
AU  - Milovanović, Milan R.
AU  - Zarić, Snežana D.
PY  - 2022
UR  - http://cherry.chem.bg.ac.rs/handle/123456789/5698
AB  - In the study of hydrogen bonds between noncoordinated and metal-coordinated ethylenediamine and a water molecule, the data in the Cambridge Structural Database (CSD) were analyzed and DFT calculations were performed. For coordinated ethylenediamine in the CSD, the analyzed distributions of dOH distances show a maximum in the range of 2.0–2.1 Å, while the angle α shows a maximum in the range of 150–160°. The DFT calculations were done for octahedral geometries of cobalt(III), copper(II), and nickel(II) complexes and square-planar geometry of palladium(II) complexes. The coordination of ethylenediamine to the metal ions strengthens its hydrogen bond with the water molecule. Namely, noncoordinated ethylenediamine and the water molecule have an interaction energy of −2.3 kcal/mol, while for coordinated ethylenediamine, the interacting energy spans from −4.0 to −28.0 kcal/mol depending on the metal ion and charge of the complex. The hydrogen bond energies have a good correlation with the calculated electrostatic potential on the interacting hydrogen atom. The coordination number and oxidation states of the metal have a significant influence on the electrostatic potential on the interacting hydrogen atom and the energy of hydrogen bonds.
PB  - ACS Publication
T2  - Cryst. Growth Des.
T1  - Hydrogen Bonds of Coordinated Ethylenediamine and a Water Molecule: Joint Crystallographic and Computational Study of Second Coordination Sphere
VL  - 22
IS  - 9
SP  - 5198
EP  - 5205
DO  - 10.1021/acs.cgd.2c00196
ER  - 

@article{
author = "Živković, Jelena M. and Milovanović, Milan R. and Zarić, Snežana D.",
year = "2022",
abstract = "In the study of hydrogen bonds between noncoordinated and metal-coordinated ethylenediamine and a water molecule, the data in the Cambridge Structural Database (CSD) were analyzed and DFT calculations were performed. For coordinated ethylenediamine in the CSD, the analyzed distributions of dOH distances show a maximum in the range of 2.0–2.1 Å, while the angle α shows a maximum in the range of 150–160°. The DFT calculations were done for octahedral geometries of cobalt(III), copper(II), and nickel(II) complexes and square-planar geometry of palladium(II) complexes. The coordination of ethylenediamine to the metal ions strengthens its hydrogen bond with the water molecule. Namely, noncoordinated ethylenediamine and the water molecule have an interaction energy of −2.3 kcal/mol, while for coordinated ethylenediamine, the interacting energy spans from −4.0 to −28.0 kcal/mol depending on the metal ion and charge of the complex. The hydrogen bond energies have a good correlation with the calculated electrostatic potential on the interacting hydrogen atom. The coordination number and oxidation states of the metal have a significant influence on the electrostatic potential on the interacting hydrogen atom and the energy of hydrogen bonds.",
publisher = "ACS Publication",
journal = "Cryst. Growth Des.",
title = "Hydrogen Bonds of Coordinated Ethylenediamine and a Water Molecule: Joint Crystallographic and Computational Study of Second Coordination Sphere",
volume = "22",
number = "9",
pages = "5198-5205",
doi = "10.1021/acs.cgd.2c00196"
}

Živković, J. M., Milovanović, M. R.,& Zarić, S. D.. (2022). Hydrogen Bonds of Coordinated Ethylenediamine and a Water Molecule: Joint Crystallographic and Computational Study of Second Coordination Sphere. in Cryst. Growth Des.
ACS Publication., 22(9), 5198-5205.
https://doi.org/10.1021/acs.cgd.2c00196

Živković JM, Milovanović MR, Zarić SD. Hydrogen Bonds of Coordinated Ethylenediamine and a Water Molecule: Joint Crystallographic and Computational Study of Second Coordination Sphere. in Cryst. Growth Des.. 2022;22(9):5198-5205.
doi:10.1021/acs.cgd.2c00196 .

Živković, Jelena M., Milovanović, Milan R., Zarić, Snežana D., "Hydrogen Bonds of Coordinated Ethylenediamine and a Water Molecule: Joint Crystallographic and Computational Study of Second Coordination Sphere" in Cryst. Growth Des., 22, no. 9 (2022):5198-5205,
https://doi.org/10.1021/acs.cgd.2c00196 . .

TY  - JOUR
AU  - Živković, Jelena M.
AU  - Milovanović, Milan R.
AU  - Zarić, Snežana D.
PY  - 2022
UR  - http://cherry.chem.bg.ac.rs/handle/123456789/5699
AB  - In the study of hydrogen bonds between noncoordinated and metal-coordinated ethylenediamine and a water molecule, the data in the Cambridge Structural Database (CSD) were analyzed and DFT calculations were performed. For coordinated ethylenediamine in the CSD, the analyzed distributions of dOH distances show a maximum in the range of 2.0–2.1 Å, while the angle α shows a maximum in the range of 150–160°. The DFT calculations were done for octahedral geometries of cobalt(III), copper(II), and nickel(II) complexes and square-planar geometry of palladium(II) complexes. The coordination of ethylenediamine to the metal ions strengthens its hydrogen bond with the water molecule. Namely, noncoordinated ethylenediamine and the water molecule have an interaction energy of −2.3 kcal/mol, while for coordinated ethylenediamine, the interacting energy spans from −4.0 to −28.0 kcal/mol depending on the metal ion and charge of the complex. The hydrogen bond energies have a good correlation with the calculated electrostatic potential on the interacting hydrogen atom. The coordination number and oxidation states of the metal have a significant influence on the electrostatic potential on the interacting hydrogen atom and the energy of hydrogen bonds.
PB  - ACS Publication
T2  - Cryst. Growth Des.
T1  - Hydrogen Bonds of Coordinated Ethylenediamine and a Water Molecule: Joint Crystallographic and Computational Study of Second Coordination Sphere
VL  - 22
IS  - 9
SP  - 5198
EP  - 5205
DO  - 10.1021/acs.cgd.2c00196
ER  - 

@article{
author = "Živković, Jelena M. and Milovanović, Milan R. and Zarić, Snežana D.",
year = "2022",
abstract = "In the study of hydrogen bonds between noncoordinated and metal-coordinated ethylenediamine and a water molecule, the data in the Cambridge Structural Database (CSD) were analyzed and DFT calculations were performed. For coordinated ethylenediamine in the CSD, the analyzed distributions of dOH distances show a maximum in the range of 2.0–2.1 Å, while the angle α shows a maximum in the range of 150–160°. The DFT calculations were done for octahedral geometries of cobalt(III), copper(II), and nickel(II) complexes and square-planar geometry of palladium(II) complexes. The coordination of ethylenediamine to the metal ions strengthens its hydrogen bond with the water molecule. Namely, noncoordinated ethylenediamine and the water molecule have an interaction energy of −2.3 kcal/mol, while for coordinated ethylenediamine, the interacting energy spans from −4.0 to −28.0 kcal/mol depending on the metal ion and charge of the complex. The hydrogen bond energies have a good correlation with the calculated electrostatic potential on the interacting hydrogen atom. The coordination number and oxidation states of the metal have a significant influence on the electrostatic potential on the interacting hydrogen atom and the energy of hydrogen bonds.",
publisher = "ACS Publication",
journal = "Cryst. Growth Des.",
title = "Hydrogen Bonds of Coordinated Ethylenediamine and a Water Molecule: Joint Crystallographic and Computational Study of Second Coordination Sphere",
volume = "22",
number = "9",
pages = "5198-5205",
doi = "10.1021/acs.cgd.2c00196"
}

Živković, J. M., Milovanović, M. R.,& Zarić, S. D.. (2022). Hydrogen Bonds of Coordinated Ethylenediamine and a Water Molecule: Joint Crystallographic and Computational Study of Second Coordination Sphere. in Cryst. Growth Des.
ACS Publication., 22(9), 5198-5205.
https://doi.org/10.1021/acs.cgd.2c00196

Živković JM, Milovanović MR, Zarić SD. Hydrogen Bonds of Coordinated Ethylenediamine and a Water Molecule: Joint Crystallographic and Computational Study of Second Coordination Sphere. in Cryst. Growth Des.. 2022;22(9):5198-5205.
doi:10.1021/acs.cgd.2c00196 .

Živković, Jelena M., Milovanović, Milan R., Zarić, Snežana D., "Hydrogen Bonds of Coordinated Ethylenediamine and a Water Molecule: Joint Crystallographic and Computational Study of Second Coordination Sphere" in Cryst. Growth Des., 22, no. 9 (2022):5198-5205,
https://doi.org/10.1021/acs.cgd.2c00196 . .

TY  - DATA
AU  - Živković, Jelena M.
AU  - Milovanović, Milan R.
AU  - Zarić, Snežana D.
PY  - 2022
UR  - http://cherry.chem.bg.ac.rs/handle/123456789/5700
AB  - In the study of hydrogen bonds between noncoordinated and metal-coordinated ethylenediamine and a water molecule, the data in the Cambridge Structural Database (CSD) were analyzed and DFT calculations were performed. For coordinated ethylenediamine in the CSD, the analyzed distributions of dOH distances show a maximum in the range of 2.0–2.1 Å, while the angle α shows a maximum in the range of 150–160°. The DFT calculations were done for octahedral geometries of cobalt(III), copper(II), and nickel(II) complexes and square-planar geometry of palladium(II) complexes. The coordination of ethylenediamine to the metal ions strengthens its hydrogen bond with the water molecule. Namely, noncoordinated ethylenediamine and the water molecule have an interaction energy of −2.3 kcal/mol, while for coordinated ethylenediamine, the interacting energy spans from −4.0 to −28.0 kcal/mol depending on the metal ion and charge of the complex. The hydrogen bond energies have a good correlation with the calculated electrostatic potential on the interacting hydrogen atom. The coordination number and oxidation states of the metal have a significant influence on the electrostatic potential on the interacting hydrogen atom and the energy of hydrogen bonds.
PB  - ACS Publication
T2  - Cryst. Growth Des.
T1  - Supplementary material for: Živković, J. M., Milovanović, M. R.,& Zarić, S. D.. (2022). Hydrogen Bonds of Coordinated Ethylenediamine and a Water Molecule: Joint Crystallographic and Computational Study of Second Coordination Sphere. in Cryst. Growth Des.
ACS Publication., 22(9), 5198-5205.
https://doi.org/10.1021/acs.cgd.2c00196
UR  - https://hdl.handle.net/21.15107/rcub_cherry_5700
ER  - 

@misc{
author = "Živković, Jelena M. and Milovanović, Milan R. and Zarić, Snežana D.",
year = "2022",
abstract = "In the study of hydrogen bonds between noncoordinated and metal-coordinated ethylenediamine and a water molecule, the data in the Cambridge Structural Database (CSD) were analyzed and DFT calculations were performed. For coordinated ethylenediamine in the CSD, the analyzed distributions of dOH distances show a maximum in the range of 2.0–2.1 Å, while the angle α shows a maximum in the range of 150–160°. The DFT calculations were done for octahedral geometries of cobalt(III), copper(II), and nickel(II) complexes and square-planar geometry of palladium(II) complexes. The coordination of ethylenediamine to the metal ions strengthens its hydrogen bond with the water molecule. Namely, noncoordinated ethylenediamine and the water molecule have an interaction energy of −2.3 kcal/mol, while for coordinated ethylenediamine, the interacting energy spans from −4.0 to −28.0 kcal/mol depending on the metal ion and charge of the complex. The hydrogen bond energies have a good correlation with the calculated electrostatic potential on the interacting hydrogen atom. The coordination number and oxidation states of the metal have a significant influence on the electrostatic potential on the interacting hydrogen atom and the energy of hydrogen bonds.",
publisher = "ACS Publication",
journal = "Cryst. Growth Des.",
title = "Supplementary material for: Živković, J. M., Milovanović, M. R.,& Zarić, S. D.. (2022). Hydrogen Bonds of Coordinated Ethylenediamine and a Water Molecule: Joint Crystallographic and Computational Study of Second Coordination Sphere. in Cryst. Growth Des.
ACS Publication., 22(9), 5198-5205.
https://doi.org/10.1021/acs.cgd.2c00196",
url = "https://hdl.handle.net/21.15107/rcub_cherry_5700"
}

Živković, J. M., Milovanović, M. R.,& Zarić, S. D.. (2022). Supplementary material for: Živković, J. M., Milovanović, M. R.,& Zarić, S. D.. (2022). Hydrogen Bonds of Coordinated Ethylenediamine and a Water Molecule: Joint Crystallographic and Computational Study of Second Coordination Sphere. in Cryst. Growth Des.
ACS Publication., 22(9), 5198-5205.
https://doi.org/10.1021/acs.cgd.2c00196. in Cryst. Growth Des.
ACS Publication..
https://hdl.handle.net/21.15107/rcub_cherry_5700

Živković JM, Milovanović MR, Zarić SD. Supplementary material for: Živković, J. M., Milovanović, M. R.,& Zarić, S. D.. (2022). Hydrogen Bonds of Coordinated Ethylenediamine and a Water Molecule: Joint Crystallographic and Computational Study of Second Coordination Sphere. in Cryst. Growth Des.
ACS Publication., 22(9), 5198-5205.
https://doi.org/10.1021/acs.cgd.2c00196. in Cryst. Growth Des.. 2022;.
https://hdl.handle.net/21.15107/rcub_cherry_5700 .

Živković, Jelena M., Milovanović, Milan R., Zarić, Snežana D., "Supplementary material for: Živković, J. M., Milovanović, M. R.,& Zarić, S. D.. (2022). Hydrogen Bonds of Coordinated Ethylenediamine and a Water Molecule: Joint Crystallographic and Computational Study of Second Coordination Sphere. in Cryst. Growth Des.
ACS Publication., 22(9), 5198-5205.
https://doi.org/10.1021/acs.cgd.2c00196" in Cryst. Growth Des. (2022),
https://hdl.handle.net/21.15107/rcub_cherry_5700 .

TY  - JOUR
AU  - Milovanović, Milan R.
AU  - Stanković, Ivana M.
AU  - Živković, Jelena M.
AU  - Ninković, Dragan
AU  - Hall, Michael B.
AU  - Zarić, Snežana D.
AU  - Macgillivray, L. R.
PY  - 2022
UR  - http://cherry.chem.bg.ac.rs/handle/123456789/5638
AB  - All water-water contacts in the crystal structures from the Cambridge Structural Database with d OO ≤ 4.0 Å have been found. These contacts were analysed on the basis of their geometries and interaction energies from CCSD(T)/CBS calculations. The results show 6729 attractive water-water contacts, of which 4717 are classical hydrogen bonds (d OH ≤ 3.0 Å and α ≥ 120°) with most being stronger than -3.3 kcal mol-1. Beyond the region of these hydrogen bonds, there is a large number of attractive interactions (2062). The majority are antiparallel dipolar interactions, where the O - H bonds of two water molecules lying in parallel planes are oriented antiparallel to each other. Developing geometric criteria for these antiparallel dipoles (β1, β2 ≥ 160°, 80 ≤ α ≤ 140° and T HOHO > 40°) yielded 1282 attractive contacts. The interaction energies of these antiparallel oriented water molecules are up to -4.7 kcal mol-1, while most of the contacts have interaction energies in the range -0.9 to -2.1 kcal mol-1. This study suggests that the geometric criteria for defining attractive water-water interactions should be broader than the classical hydrogen-bonding criteria, a change that may reveal undiscovered and unappreciated interactions controlling molecular structure and chemistry. © 2022 Milan R. Milovanović et al.
PB  - International Union of Crystallography
T2  - IUCrJ
T1  - Water: new aspect of hydrogen bonding in the solid state
VL  - 9
IS  - 5
SP  - 639
EP  - 647
DO  - 10.1107/S2052252522006728
ER  - 

@article{
author = "Milovanović, Milan R. and Stanković, Ivana M. and Živković, Jelena M. and Ninković, Dragan and Hall, Michael B. and Zarić, Snežana D. and Macgillivray, L. R.",
year = "2022",
abstract = "All water-water contacts in the crystal structures from the Cambridge Structural Database with d OO ≤ 4.0 Å have been found. These contacts were analysed on the basis of their geometries and interaction energies from CCSD(T)/CBS calculations. The results show 6729 attractive water-water contacts, of which 4717 are classical hydrogen bonds (d OH ≤ 3.0 Å and α ≥ 120°) with most being stronger than -3.3 kcal mol-1. Beyond the region of these hydrogen bonds, there is a large number of attractive interactions (2062). The majority are antiparallel dipolar interactions, where the O - H bonds of two water molecules lying in parallel planes are oriented antiparallel to each other. Developing geometric criteria for these antiparallel dipoles (β1, β2 ≥ 160°, 80 ≤ α ≤ 140° and T HOHO > 40°) yielded 1282 attractive contacts. The interaction energies of these antiparallel oriented water molecules are up to -4.7 kcal mol-1, while most of the contacts have interaction energies in the range -0.9 to -2.1 kcal mol-1. This study suggests that the geometric criteria for defining attractive water-water interactions should be broader than the classical hydrogen-bonding criteria, a change that may reveal undiscovered and unappreciated interactions controlling molecular structure and chemistry. © 2022 Milan R. Milovanović et al.",
publisher = "International Union of Crystallography",
journal = "IUCrJ",
title = "Water: new aspect of hydrogen bonding in the solid state",
volume = "9",
number = "5",
pages = "639-647",
doi = "10.1107/S2052252522006728"
}

Milovanović, M. R., Stanković, I. M., Živković, J. M., Ninković, D., Hall, M. B., Zarić, S. D.,& Macgillivray, L. R.. (2022). Water: new aspect of hydrogen bonding in the solid state. in IUCrJ
International Union of Crystallography., 9(5), 639-647.
https://doi.org/10.1107/S2052252522006728

Milovanović MR, Stanković IM, Živković JM, Ninković D, Hall MB, Zarić SD, Macgillivray LR. Water: new aspect of hydrogen bonding in the solid state. in IUCrJ. 2022;9(5):639-647.
doi:10.1107/S2052252522006728 .

Milovanović, Milan R., Stanković, Ivana M., Živković, Jelena M., Ninković, Dragan, Hall, Michael B., Zarić, Snežana D., Macgillivray, L. R., "Water: new aspect of hydrogen bonding in the solid state" in IUCrJ, 9, no. 5 (2022):639-647,
https://doi.org/10.1107/S2052252522006728 . .

TY  - CONF
AU  - Milovanović, Milan R.
AU  - Živković, Jelena M.
AU  - Ninković, Dragan B.
AU  - Stanković, Ivana M.
AU  - Zarić, Snežana D.
PY  - 2021
UR  - http://cherry.chem.bg.ac.rs/handle/123456789/6355
AB  - Water molecules are omnipresent in nature and are a key part of many life processes. Due its ability of hydrogen binding water molecule plays an important role in the packing of small molecule crystal structures. Over the past years, the structure of a water molecule has been intensively studied. [1] The experimental values for a free water molecule in the gas phase are the bond angle (H–O–H) of 104.52 ± 0.05° and the bond (O–H) length of 0.9572 ± 0.0003 Å. [2] Neutron diffraction experiments of liquid water showed that the bond angle increases to 106.1 ± 1.8° and the bond length increases to 0.970 ± 0.005 Å. [3] Most of the bond angles in structures of ice have values close to a tetrahedral angle. However, in some of the ice structures, the bond angles and bond lengths remarkably deviates. Calculations based on the spectroscopic potential energy surface showed the equilibrium structure of a water molecule with the bond angle of 104.501 ± 0.005° and the bond length of 0.95785 ± 0.00005 Å. [4] In this study, [5] we performed an analysis of non-coordinated water containing structures archived in Cambridge Structural Database (CSD) as well as ab-initio calculations on a range of bond angles and bond lengths of water molecule. The results of the analysis of crystal structures solved by neutron as well as by X-ray diffraction analysis showed a large discrepancy of both the bond angle and bond length values. Namely, the ranges of the bond angle and the average bond lengths of neutron solved structures having R factor ≤ 0.05 are from 100.74° to 113.92° and from 0.91 Å to 0.99 Å respectively. The corresponding range of the bond angle of X-ray solved structures is from 13.27° to 180.00°. High level ab initio calculations predicted a possibility for energetically low-cost (±1 kcal mol–1) changes of both the bond angle and bond lengths in a wide range, from 96.4° to 112.8° (Fig. 1) and from 0.930 A to 0.989 A (Fig. 1), respectively. Consequently, it would lead to at least 15% of X-ray solved structures that contain questionable water molecule geometries.
PB  - Wiley
C3  - 25th Congress and General Assembly of the International Union of Crystallography, Prague, Czech Republic, August 2021
T1  - How flexible is the water molecule structure? Cambridge Structural Database and ab initio calculations study.
UR  - https://hdl.handle.net/21.15107/rcub_cherry_6355
ER  - 

@conference{
author = "Milovanović, Milan R. and Živković, Jelena M. and Ninković, Dragan B. and Stanković, Ivana M. and Zarić, Snežana D.",
year = "2021",
abstract = "Water molecules are omnipresent in nature and are a key part of many life processes. Due its ability of hydrogen binding water molecule plays an important role in the packing of small molecule crystal structures. Over the past years, the structure of a water molecule has been intensively studied. [1] The experimental values for a free water molecule in the gas phase are the bond angle (H–O–H) of 104.52 ± 0.05° and the bond (O–H) length of 0.9572 ± 0.0003 Å. [2] Neutron diffraction experiments of liquid water showed that the bond angle increases to 106.1 ± 1.8° and the bond length increases to 0.970 ± 0.005 Å. [3] Most of the bond angles in structures of ice have values close to a tetrahedral angle. However, in some of the ice structures, the bond angles and bond lengths remarkably deviates. Calculations based on the spectroscopic potential energy surface showed the equilibrium structure of a water molecule with the bond angle of 104.501 ± 0.005° and the bond length of 0.95785 ± 0.00005 Å. [4] In this study, [5] we performed an analysis of non-coordinated water containing structures archived in Cambridge Structural Database (CSD) as well as ab-initio calculations on a range of bond angles and bond lengths of water molecule. The results of the analysis of crystal structures solved by neutron as well as by X-ray diffraction analysis showed a large discrepancy of both the bond angle and bond length values. Namely, the ranges of the bond angle and the average bond lengths of neutron solved structures having R factor ≤ 0.05 are from 100.74° to 113.92° and from 0.91 Å to 0.99 Å respectively. The corresponding range of the bond angle of X-ray solved structures is from 13.27° to 180.00°. High level ab initio calculations predicted a possibility for energetically low-cost (±1 kcal mol–1) changes of both the bond angle and bond lengths in a wide range, from 96.4° to 112.8° (Fig. 1) and from 0.930 A to 0.989 A (Fig. 1), respectively. Consequently, it would lead to at least 15% of X-ray solved structures that contain questionable water molecule geometries.",
publisher = "Wiley",
journal = "25th Congress and General Assembly of the International Union of Crystallography, Prague, Czech Republic, August 2021",
title = "How flexible is the water molecule structure? Cambridge Structural Database and ab initio calculations study.",
url = "https://hdl.handle.net/21.15107/rcub_cherry_6355"
}

Milovanović, M. R., Živković, J. M., Ninković, D. B., Stanković, I. M.,& Zarić, S. D.. (2021). How flexible is the water molecule structure? Cambridge Structural Database and ab initio calculations study.. in 25th Congress and General Assembly of the International Union of Crystallography, Prague, Czech Republic, August 2021
Wiley..
https://hdl.handle.net/21.15107/rcub_cherry_6355

Milovanović MR, Živković JM, Ninković DB, Stanković IM, Zarić SD. How flexible is the water molecule structure? Cambridge Structural Database and ab initio calculations study.. in 25th Congress and General Assembly of the International Union of Crystallography, Prague, Czech Republic, August 2021. 2021;.
https://hdl.handle.net/21.15107/rcub_cherry_6355 .

Milovanović, Milan R., Živković, Jelena M., Ninković, Dragan B., Stanković, Ivana M., Zarić, Snežana D., "How flexible is the water molecule structure? Cambridge Structural Database and ab initio calculations study." in 25th Congress and General Assembly of the International Union of Crystallography, Prague, Czech Republic, August 2021 (2021),
https://hdl.handle.net/21.15107/rcub_cherry_6355 .

TY  - CONF
AU  - Milovanović, Milan R.
AU  - Živković, Jelena M.
AU  - Ninković, Dragan
AU  - Blagojević Filipović, Jelena P.
AU  - Vojislavljević-Vasilev, Dubravka
AU  - Veljković, Ivana S.
AU  - Stanković, Ivana M.
AU  - Malenov, Dušan P.
AU  - Medaković, Vesna
AU  - Veljković, Dušan Ž.
AU  - Zarić, Snežana D.
PY  - 2021
UR  - http://cherry.chem.bg.ac.rs/handle/123456789/5275
UR  - https://iucr25.org/
AB  - In the recent review it was point out that the crystal structures in the Cambridge Structural Database (CSD), collected, have contribute
to various fields of chemical research such as geometries of molecules, noncovalent interactions of molecules, and large assemblies of
molecules. The CSD also contributed to the study and the design of biologically active molecules and the study of gas storage and
delivery [1].
In our group we use analysis of the crystal structures in the CSD to recognize and characterize new types of noncovalent interactions
and to study already known noncovalent interactions. Based on the data from the CSD we can determine existence of the interactions,
frequency of the interactions, and preferred geometries of the interactions in the crystal structures. In addition, we perform quantum
chemical calculations to evaluate the energies of the interactions. Based on the calculated potential energy surfaces for the
interactions, we can determine the most stable geometries, as well as stability of various geometries. We also can determine the
interaction energies for the preferred geometries in the crystal structures. In the cases where the most preferred geometries in the
crystal structures are not the most stable geometries at the potential energy surface, one can find significant influence of the
supramolecular structures in the crystals.
Using this methodology our group recognized stacking interactions of planar metal-chelate rings; stacking interactions with organic
aromatic rings and stacking interactions between two chelate rings. The calculated energies indicate strong stacking interactions of
metal-chelate rings; the stacking of metal-chelate rings is stronger than stacking between two benzene molecules [2]. The data indicate
influence of the metal and ligand type in the metal chelate ring on the strength of the interactions. Our results also indicate strong
stacking interactions of coordinated aromatic rings [3]. Studies of interactions of coordinated water indicate stronger hydrogen bonds
and stronger OH/π interactions of coordinated in comparison to noncoordianted water molecule [4,5]. The calculations on OH/M
interactions between metal ion in square-planar complexes and water molecule indicate that these interactions are among the strongest
hydrogen bonds in any molecular system [6].
The studies on stacking interactions of benzene molecules in the crystal structures in the CSD show preference for interactions at large
horizontal displacements, while high level quantum chemical calculations indicate significantly strong interactions at large offsets; the
energy is 70% of the strongest stacking geometry [7].
PB  - Wiley
C3  - 25th Congress and General Assembly of the International Union of Crystallography, Prague, Czech Republic, August 2021
T1  - Study of noncovalent interactions using crystal structure data in the Cambridge Structural Database
VL  - A77
SP  - C192
UR  - https://hdl.handle.net/21.15107/rcub_cherry_5275
ER  - 

@conference{
author = "Milovanović, Milan R. and Živković, Jelena M. and Ninković, Dragan and Blagojević Filipović, Jelena P. and Vojislavljević-Vasilev, Dubravka and Veljković, Ivana S. and Stanković, Ivana M. and Malenov, Dušan P. and Medaković, Vesna and Veljković, Dušan Ž. and Zarić, Snežana D.",
year = "2021",
abstract = "In the recent review it was point out that the crystal structures in the Cambridge Structural Database (CSD), collected, have contribute
to various fields of chemical research such as geometries of molecules, noncovalent interactions of molecules, and large assemblies of
molecules. The CSD also contributed to the study and the design of biologically active molecules and the study of gas storage and
delivery [1].
In our group we use analysis of the crystal structures in the CSD to recognize and characterize new types of noncovalent interactions
and to study already known noncovalent interactions. Based on the data from the CSD we can determine existence of the interactions,
frequency of the interactions, and preferred geometries of the interactions in the crystal structures. In addition, we perform quantum
chemical calculations to evaluate the energies of the interactions. Based on the calculated potential energy surfaces for the
interactions, we can determine the most stable geometries, as well as stability of various geometries. We also can determine the
interaction energies for the preferred geometries in the crystal structures. In the cases where the most preferred geometries in the
crystal structures are not the most stable geometries at the potential energy surface, one can find significant influence of the
supramolecular structures in the crystals.
Using this methodology our group recognized stacking interactions of planar metal-chelate rings; stacking interactions with organic
aromatic rings and stacking interactions between two chelate rings. The calculated energies indicate strong stacking interactions of
metal-chelate rings; the stacking of metal-chelate rings is stronger than stacking between two benzene molecules [2]. The data indicate
influence of the metal and ligand type in the metal chelate ring on the strength of the interactions. Our results also indicate strong
stacking interactions of coordinated aromatic rings [3]. Studies of interactions of coordinated water indicate stronger hydrogen bonds
and stronger OH/π interactions of coordinated in comparison to noncoordianted water molecule [4,5]. The calculations on OH/M
interactions between metal ion in square-planar complexes and water molecule indicate that these interactions are among the strongest
hydrogen bonds in any molecular system [6].
The studies on stacking interactions of benzene molecules in the crystal structures in the CSD show preference for interactions at large
horizontal displacements, while high level quantum chemical calculations indicate significantly strong interactions at large offsets; the
energy is 70% of the strongest stacking geometry [7].",
publisher = "Wiley",
journal = "25th Congress and General Assembly of the International Union of Crystallography, Prague, Czech Republic, August 2021",
title = "Study of noncovalent interactions using crystal structure data in the Cambridge Structural Database",
volume = "A77",
pages = "C192",
url = "https://hdl.handle.net/21.15107/rcub_cherry_5275"
}

Milovanović, M. R., Živković, J. M., Ninković, D., Blagojević Filipović, J. P., Vojislavljević-Vasilev, D., Veljković, I. S., Stanković, I. M., Malenov, D. P., Medaković, V., Veljković, D. Ž.,& Zarić, S. D.. (2021). Study of noncovalent interactions using crystal structure data in the Cambridge Structural Database. in 25th Congress and General Assembly of the International Union of Crystallography, Prague, Czech Republic, August 2021
Wiley., A77, C192.
https://hdl.handle.net/21.15107/rcub_cherry_5275

Milovanović MR, Živković JM, Ninković D, Blagojević Filipović JP, Vojislavljević-Vasilev D, Veljković IS, Stanković IM, Malenov DP, Medaković V, Veljković DŽ, Zarić SD. Study of noncovalent interactions using crystal structure data in the Cambridge Structural Database. in 25th Congress and General Assembly of the International Union of Crystallography, Prague, Czech Republic, August 2021. 2021;A77:C192.
https://hdl.handle.net/21.15107/rcub_cherry_5275 .

Milovanović, Milan R., Živković, Jelena M., Ninković, Dragan, Blagojević Filipović, Jelena P., Vojislavljević-Vasilev, Dubravka, Veljković, Ivana S., Stanković, Ivana M., Malenov, Dušan P., Medaković, Vesna, Veljković, Dušan Ž., Zarić, Snežana D., "Study of noncovalent interactions using crystal structure data in the Cambridge Structural Database" in 25th Congress and General Assembly of the International Union of Crystallography, Prague, Czech Republic, August 2021, A77 (2021):C192,
https://hdl.handle.net/21.15107/rcub_cherry_5275 .

TY  - CONF
AU  - Milovanović, Milan R.
AU  - Živković, Jelena M.
AU  - Ninković, Dragan
AU  - Blagojević Filipović, Jelena P.
AU  - Vojislavljević-Vasilev, Dubravka
AU  - Veljković, Ivana S.
AU  - Stanković, Ivana M.
AU  - Malenov, Dušan P.
AU  - Medaković, Vesna
AU  - Veljković, Dušan Ž.
AU  - Zarić, Snežana D.
PY  - 2021
UR  - http://cherry.chem.bg.ac.rs/handle/123456789/5274
AB  - The analysis of the crystal structures in the CSD was used to recognize and characterize new types of noncovalent interactions. It was also used to study already known noncovalent interactions. Based on the data from the CSD we can determine existence of the interactions, frequency of the interactions, and preferred geometries of the interactions in the crystal structures [1,2].
The quantum chemical calculations were performed to evaluate the energies of the interactions. For the preferred geometries in the crystal structures we can calculate the interaction energies. By calculating potential energy surfaces for the interactions, we can determine the most stable geometries, as well as stability of various geometries [1,2].
Using this methodology our group recognized stacking interactions of planar metal-chelate rings; stacking interactions with organic aromatic rings, and stacking interactions between two chelate rings. The calculated energies showed that the stacking of metal-chelate rings is stronger than stacking between two benzene molecules. Studies of interactions of coordinated ligands indicate stronger noncovalent interactions that interactions of noncoordinated molecules [2].

REFERENCES
[1] Ninković, D. B., Blagojević Filipović, J. P., Hall, M. B., Brothers, E. N., Zarić, S. D. (2020) ACS Central Science, 6, 420.
[2] Malenov, D. P., Zarić, S. D. (2020) Cood. Chem. Rev. 419, 213338.
PB  - Society of Physical Chemists of Serbia
C3  - 15th International Conference on Fundamental and Applied Aspects of Physical Chemistry, Book of Abstracts
T1  - Study of noncovalent interactions using crystal strucutre data and quantum chemical calculations
UR  - https://hdl.handle.net/21.15107/rcub_cherry_5274
ER  - 

@conference{
author = "Milovanović, Milan R. and Živković, Jelena M. and Ninković, Dragan and Blagojević Filipović, Jelena P. and Vojislavljević-Vasilev, Dubravka and Veljković, Ivana S. and Stanković, Ivana M. and Malenov, Dušan P. and Medaković, Vesna and Veljković, Dušan Ž. and Zarić, Snežana D.",
year = "2021",
abstract = "The analysis of the crystal structures in the CSD was used to recognize and characterize new types of noncovalent interactions. It was also used to study already known noncovalent interactions. Based on the data from the CSD we can determine existence of the interactions, frequency of the interactions, and preferred geometries of the interactions in the crystal structures [1,2].
The quantum chemical calculations were performed to evaluate the energies of the interactions. For the preferred geometries in the crystal structures we can calculate the interaction energies. By calculating potential energy surfaces for the interactions, we can determine the most stable geometries, as well as stability of various geometries [1,2].
Using this methodology our group recognized stacking interactions of planar metal-chelate rings; stacking interactions with organic aromatic rings, and stacking interactions between two chelate rings. The calculated energies showed that the stacking of metal-chelate rings is stronger than stacking between two benzene molecules. Studies of interactions of coordinated ligands indicate stronger noncovalent interactions that interactions of noncoordinated molecules [2].

REFERENCES
[1] Ninković, D. B., Blagojević Filipović, J. P., Hall, M. B., Brothers, E. N., Zarić, S. D. (2020) ACS Central Science, 6, 420.
[2] Malenov, D. P., Zarić, S. D. (2020) Cood. Chem. Rev. 419, 213338.",
publisher = "Society of Physical Chemists of Serbia",
journal = "15th International Conference on Fundamental and Applied Aspects of Physical Chemistry, Book of Abstracts",
title = "Study of noncovalent interactions using crystal strucutre data and quantum chemical calculations",
url = "https://hdl.handle.net/21.15107/rcub_cherry_5274"
}

Milovanović, M. R., Živković, J. M., Ninković, D., Blagojević Filipović, J. P., Vojislavljević-Vasilev, D., Veljković, I. S., Stanković, I. M., Malenov, D. P., Medaković, V., Veljković, D. Ž.,& Zarić, S. D.. (2021). Study of noncovalent interactions using crystal strucutre data and quantum chemical calculations. in 15th International Conference on Fundamental and Applied Aspects of Physical Chemistry, Book of Abstracts
Society of Physical Chemists of Serbia..
https://hdl.handle.net/21.15107/rcub_cherry_5274

Milovanović MR, Živković JM, Ninković D, Blagojević Filipović JP, Vojislavljević-Vasilev D, Veljković IS, Stanković IM, Malenov DP, Medaković V, Veljković DŽ, Zarić SD. Study of noncovalent interactions using crystal strucutre data and quantum chemical calculations. in 15th International Conference on Fundamental and Applied Aspects of Physical Chemistry, Book of Abstracts. 2021;.
https://hdl.handle.net/21.15107/rcub_cherry_5274 .

Milovanović, Milan R., Živković, Jelena M., Ninković, Dragan, Blagojević Filipović, Jelena P., Vojislavljević-Vasilev, Dubravka, Veljković, Ivana S., Stanković, Ivana M., Malenov, Dušan P., Medaković, Vesna, Veljković, Dušan Ž., Zarić, Snežana D., "Study of noncovalent interactions using crystal strucutre data and quantum chemical calculations" in 15th International Conference on Fundamental and Applied Aspects of Physical Chemistry, Book of Abstracts (2021),
https://hdl.handle.net/21.15107/rcub_cherry_5274 .

TY  - CONF
AU  - Milovanović, Milan R.
AU  - Živković, Jelena M.
AU  - Ninković, Dragan
AU  - Blagojević Filipović, Jelena P.
AU  - Vojislavljević-Vasilev, Dubravka
AU  - Veljković, Ivana S.
AU  - Stanković, Ivana M.
AU  - Malenov, Dušan P.
AU  - Medaković, Vesna
AU  - Veljković, Dušan Ž.
AU  - Zarić, Snežana D.
PY  - 2021
UR  - http://cherry.chem.bg.ac.rs/handle/123456789/5354
AB  - The analysis of the crystal structures in the CSD was used to recognize and characterize new types of noncovalent interactions. It was also used to study already known noncovalent interactions. Based on the data from the CSD we can determine existence of the interactions, frequency of the interactions, and preferred geometries of the interactions in the crystal structures [1,2].
The quantum chemical calculations were performed to evaluate the energies of the interactions.
For the preferred geometries in the crystal structures we can calculate the interaction energies. By
calculating potential energy surfaces for the interactions, we can determine the most stable
geometries, as well as stability of various geometries [1,2].
Using this methodology our group recognized stacking interactions of planar metal-chelate rings;
stacking interactions with organic aromatic rings, and stacking interactions between two chelate rings.
The calculated energies showed that the stacking of metal-chelate rings is stronger than stacking
between two benzene molecules. Studies of interactions of coordinated ligands indicate stronger
noncovalent interactions that interactions of noncoordinated molecules [2].
PB  - Society of Physical Chemists of Serbia
C3  - 15th International Conference on Fundamental and Applied Aspects of Physical Chemistry, PC2021, 22-22
T1  - Study of noncovalent interactions using crystal strucutre data and quantum chemical calculations
SP  - 22
EP  - 22
UR  - https://hdl.handle.net/21.15107/rcub_cherry_5354
ER  - 

@conference{
author = "Milovanović, Milan R. and Živković, Jelena M. and Ninković, Dragan and Blagojević Filipović, Jelena P. and Vojislavljević-Vasilev, Dubravka and Veljković, Ivana S. and Stanković, Ivana M. and Malenov, Dušan P. and Medaković, Vesna and Veljković, Dušan Ž. and Zarić, Snežana D.",
year = "2021",
abstract = "The analysis of the crystal structures in the CSD was used to recognize and characterize new types of noncovalent interactions. It was also used to study already known noncovalent interactions. Based on the data from the CSD we can determine existence of the interactions, frequency of the interactions, and preferred geometries of the interactions in the crystal structures [1,2].
The quantum chemical calculations were performed to evaluate the energies of the interactions.
For the preferred geometries in the crystal structures we can calculate the interaction energies. By
calculating potential energy surfaces for the interactions, we can determine the most stable
geometries, as well as stability of various geometries [1,2].
Using this methodology our group recognized stacking interactions of planar metal-chelate rings;
stacking interactions with organic aromatic rings, and stacking interactions between two chelate rings.
The calculated energies showed that the stacking of metal-chelate rings is stronger than stacking
between two benzene molecules. Studies of interactions of coordinated ligands indicate stronger
noncovalent interactions that interactions of noncoordinated molecules [2].",
publisher = "Society of Physical Chemists of Serbia",
journal = "15th International Conference on Fundamental and Applied Aspects of Physical Chemistry, PC2021, 22-22",
title = "Study of noncovalent interactions using crystal strucutre data and quantum chemical calculations",
pages = "22-22",
url = "https://hdl.handle.net/21.15107/rcub_cherry_5354"
}

Milovanović, M. R., Živković, J. M., Ninković, D., Blagojević Filipović, J. P., Vojislavljević-Vasilev, D., Veljković, I. S., Stanković, I. M., Malenov, D. P., Medaković, V., Veljković, D. Ž.,& Zarić, S. D.. (2021). Study of noncovalent interactions using crystal strucutre data and quantum chemical calculations. in 15th International Conference on Fundamental and Applied Aspects of Physical Chemistry, PC2021, 22-22
Society of Physical Chemists of Serbia., 22-22.
https://hdl.handle.net/21.15107/rcub_cherry_5354

Milovanović MR, Živković JM, Ninković D, Blagojević Filipović JP, Vojislavljević-Vasilev D, Veljković IS, Stanković IM, Malenov DP, Medaković V, Veljković DŽ, Zarić SD. Study of noncovalent interactions using crystal strucutre data and quantum chemical calculations. in 15th International Conference on Fundamental and Applied Aspects of Physical Chemistry, PC2021, 22-22. 2021;:22-22.
https://hdl.handle.net/21.15107/rcub_cherry_5354 .

Milovanović, Milan R., Živković, Jelena M., Ninković, Dragan, Blagojević Filipović, Jelena P., Vojislavljević-Vasilev, Dubravka, Veljković, Ivana S., Stanković, Ivana M., Malenov, Dušan P., Medaković, Vesna, Veljković, Dušan Ž., Zarić, Snežana D., "Study of noncovalent interactions using crystal strucutre data and quantum chemical calculations" in 15th International Conference on Fundamental and Applied Aspects of Physical Chemistry, PC2021, 22-22 (2021):22-22,
https://hdl.handle.net/21.15107/rcub_cherry_5354 .

TY  - JOUR
AU  - Milovanović, Milan R.
AU  - Boucher, Mélanie
AU  - Cornaton, Yann
AU  - Zarić, Snežana D.
AU  - Pfeffer, Michel
AU  - Djukic, Jean-Pierre
PY  - 2021
UR  - https://onlinelibrary.wiley.com/doi/abs/10.1002/ejic.202100750
UR  - C:\Users\Ana\Zotero\storage\ZAYTN3C5\Milovanović et al. - 2021 - The Thermochemistry of Alkyne Insertion into a Pal.pdf
UR  - C:\Users\Ana\Zotero\storage\JYEI976E\ejic.html
UR  - http://cherry.chem.bg.ac.rs/handle/123456789/4783
AB  - In an effort to determine the thermochemistry of established organometallic transformation, the well documented reaction of alkynes with a palladacycle was investigated by isothermal titration calorimetry (ITC). Although the mechanism of the insertion of unsaturated substrates into the Pd−C bond of cyclopalladated compounds is known, no information is available so far about their thermochemistry. The enthalpies of the reactions of Ph−C≡C−Ph and MeOC(O)−C≡C(O)COMe with the bisacetonitrilo salt of the N,N-benzylamine palladacycle were determined by ITC in chlorobenzene after having optimized the conditions to ensure that only the double and a single insertion of alkynes were occurring respectively. The reaction energy profile established by DFT for the double insertion process involving Ph−C≡C−Ph confirmed earlier conclusions on the rate determining character of the first insertion. Further computations of reaction enthalpies reveal significant discrepancies between ITC and DFT-D/continuum solvation enthalpies, that are suspected to arise from an unexpected explicit noncovalent interaction of PhCl with the components of the reaction.
PB  - Wiley
T2  - European Journal of Inorganic Chemistry
T1  - The Thermochemistry of Alkyne Insertion into a Palladacycle Outlines the Solvation Conundrum in DFT
VL  - 2021
IS  - 45
SP  - 4690
EP  - 4699
DO  - 10.1002/ejic.202100750
ER  - 

@article{
author = "Milovanović, Milan R. and Boucher, Mélanie and Cornaton, Yann and Zarić, Snežana D. and Pfeffer, Michel and Djukic, Jean-Pierre",
year = "2021",
abstract = "In an effort to determine the thermochemistry of established organometallic transformation, the well documented reaction of alkynes with a palladacycle was investigated by isothermal titration calorimetry (ITC). Although the mechanism of the insertion of unsaturated substrates into the Pd−C bond of cyclopalladated compounds is known, no information is available so far about their thermochemistry. The enthalpies of the reactions of Ph−C≡C−Ph and MeOC(O)−C≡C(O)COMe with the bisacetonitrilo salt of the N,N-benzylamine palladacycle were determined by ITC in chlorobenzene after having optimized the conditions to ensure that only the double and a single insertion of alkynes were occurring respectively. The reaction energy profile established by DFT for the double insertion process involving Ph−C≡C−Ph confirmed earlier conclusions on the rate determining character of the first insertion. Further computations of reaction enthalpies reveal significant discrepancies between ITC and DFT-D/continuum solvation enthalpies, that are suspected to arise from an unexpected explicit noncovalent interaction of PhCl with the components of the reaction.",
publisher = "Wiley",
journal = "European Journal of Inorganic Chemistry",
title = "The Thermochemistry of Alkyne Insertion into a Palladacycle Outlines the Solvation Conundrum in DFT",
volume = "2021",
number = "45",
pages = "4690-4699",
doi = "10.1002/ejic.202100750"
}

Milovanović, M. R., Boucher, M., Cornaton, Y., Zarić, S. D., Pfeffer, M.,& Djukic, J.. (2021). The Thermochemistry of Alkyne Insertion into a Palladacycle Outlines the Solvation Conundrum in DFT. in European Journal of Inorganic Chemistry
Wiley., 2021(45), 4690-4699.
https://doi.org/10.1002/ejic.202100750

Milovanović MR, Boucher M, Cornaton Y, Zarić SD, Pfeffer M, Djukic J. The Thermochemistry of Alkyne Insertion into a Palladacycle Outlines the Solvation Conundrum in DFT. in European Journal of Inorganic Chemistry. 2021;2021(45):4690-4699.
doi:10.1002/ejic.202100750 .

Milovanović, Milan R., Boucher, Mélanie, Cornaton, Yann, Zarić, Snežana D., Pfeffer, Michel, Djukic, Jean-Pierre, "The Thermochemistry of Alkyne Insertion into a Palladacycle Outlines the Solvation Conundrum in DFT" in European Journal of Inorganic Chemistry, 2021, no. 45 (2021):4690-4699,
https://doi.org/10.1002/ejic.202100750 . .

TY  - CONF
AU  - Milovanović, Milan R.
AU  - Dherbassy, Quentin
AU  - Wencel-Delord, Joanna
AU  - Colobert, Françoise
AU  - Zarić, Snežana D.
AU  - Djukic, Jean-Pierre
PY  - 2020
UR  - http://cherry.chem.bg.ac.rs/handle/123456789/6357
AB  - HFIP, i.e. 1,1,1,3,3,3-hexafluoropropan-2-ol, was found to be an exceptional medium,[1] either as solvent or co-solvent, that allows many reactions to occur.[2-5] However, the exact role and mode of action of HFIP in various chemical transformations still remains elusive. Despite many reports dealing with water/HFIP complexes, little has been published on other molecular complexes of HFIP as well as on thermochemistry of the formation of such complexes.[6]
Within this study the affinity of a series of eight different Lewis bases (3 sulfoxides, 3 Nsp2 pyridine derivatives, 1 aromatic amine, 1 cyclic aliphatic ether) to HFIP (as Lewis acid) is investigated 
experimentally by Isothermal Titration Calorimetry (ITC) and theoretically using static DFT-D calculations. Measured ITC association enthalpy values ΔHaITC spanned -9.3 kcal/mol - -14
kcal/mol. Computations including a PCM implicit solvation model produced similar exothermicity of association of all studied systems - ΔHa values ranging -8.5 – -12.7 kcal/mol. In general, most of interaction energy is due to the hydrogen bonding and not due to formation of significantly strong halogen bonds. An additional set of calculations combining implicit and explicit solvation by chlorobenzene of the reactants, pointed out the relatively low interference of the solvent with the HFIPbase complexation, which main effect is to slightly enhance the Gibbs energy of the HFIP-Lewis base association. It is speculated that the interactions of bulk HFIP with Lewis bases therefore may significantly intervene in catalytic processes not only via the dynamic miscrostructuration of the medium but also more explicitly by affecting bonds’ polarization at the Lewis bases.
C3  - The 4th International Symposium on Halogen Bonding (ISXB4), Stellenbosch University, South Africa, 2-5 November 2020
T1  - Joint ITC and DFT Study of the Affinity of Some Lewis Bases to HIFP in Solution
SP  - 161
EP  - 161
UR  - https://hdl.handle.net/21.15107/rcub_cherry_6357
ER  - 

@conference{
author = "Milovanović, Milan R. and Dherbassy, Quentin and Wencel-Delord, Joanna and Colobert, Françoise and Zarić, Snežana D. and Djukic, Jean-Pierre",
year = "2020",
abstract = "HFIP, i.e. 1,1,1,3,3,3-hexafluoropropan-2-ol, was found to be an exceptional medium,[1] either as solvent or co-solvent, that allows many reactions to occur.[2-5] However, the exact role and mode of action of HFIP in various chemical transformations still remains elusive. Despite many reports dealing with water/HFIP complexes, little has been published on other molecular complexes of HFIP as well as on thermochemistry of the formation of such complexes.[6]
Within this study the affinity of a series of eight different Lewis bases (3 sulfoxides, 3 Nsp2 pyridine derivatives, 1 aromatic amine, 1 cyclic aliphatic ether) to HFIP (as Lewis acid) is investigated 
experimentally by Isothermal Titration Calorimetry (ITC) and theoretically using static DFT-D calculations. Measured ITC association enthalpy values ΔHaITC spanned -9.3 kcal/mol - -14
kcal/mol. Computations including a PCM implicit solvation model produced similar exothermicity of association of all studied systems - ΔHa values ranging -8.5 – -12.7 kcal/mol. In general, most of interaction energy is due to the hydrogen bonding and not due to formation of significantly strong halogen bonds. An additional set of calculations combining implicit and explicit solvation by chlorobenzene of the reactants, pointed out the relatively low interference of the solvent with the HFIPbase complexation, which main effect is to slightly enhance the Gibbs energy of the HFIP-Lewis base association. It is speculated that the interactions of bulk HFIP with Lewis bases therefore may significantly intervene in catalytic processes not only via the dynamic miscrostructuration of the medium but also more explicitly by affecting bonds’ polarization at the Lewis bases.",
journal = "The 4th International Symposium on Halogen Bonding (ISXB4), Stellenbosch University, South Africa, 2-5 November 2020",
title = "Joint ITC and DFT Study of the Affinity of Some Lewis Bases to HIFP in Solution",
pages = "161-161",
url = "https://hdl.handle.net/21.15107/rcub_cherry_6357"
}

Milovanović, M. R., Dherbassy, Q., Wencel-Delord, J., Colobert, F., Zarić, S. D.,& Djukic, J.. (2020). Joint ITC and DFT Study of the Affinity of Some Lewis Bases to HIFP in Solution. in The 4th International Symposium on Halogen Bonding (ISXB4), Stellenbosch University, South Africa, 2-5 November 2020, 161-161.
https://hdl.handle.net/21.15107/rcub_cherry_6357

Milovanović MR, Dherbassy Q, Wencel-Delord J, Colobert F, Zarić SD, Djukic J. Joint ITC and DFT Study of the Affinity of Some Lewis Bases to HIFP in Solution. in The 4th International Symposium on Halogen Bonding (ISXB4), Stellenbosch University, South Africa, 2-5 November 2020. 2020;:161-161.
https://hdl.handle.net/21.15107/rcub_cherry_6357 .

Milovanović, Milan R., Dherbassy, Quentin, Wencel-Delord, Joanna, Colobert, Françoise, Zarić, Snežana D., Djukic, Jean-Pierre, "Joint ITC and DFT Study of the Affinity of Some Lewis Bases to HIFP in Solution" in The 4th International Symposium on Halogen Bonding (ISXB4), Stellenbosch University, South Africa, 2-5 November 2020 (2020):161-161,
https://hdl.handle.net/21.15107/rcub_cherry_6357 .

TY  - JOUR
AU  - Milovanović, Milan R.
AU  - Živković, Jelena M.
AU  - Ninković, Dragan
AU  - Stanković, Ivana M.
AU  - Zarić, Snežana D.
PY  - 2020
UR  - https://cherry.chem.bg.ac.rs/handle/123456789/3977
AB  - Water molecules from crystal structures archived in the CSD show a relatively large range both in the bond angle and bond lengths. High level ab initio calculations at the CCSD(T)/CBS level predicted a possibility for energetically low-cost (±1 kcal mol−1) changes of the bond angle and bond lengths in a wide range, from 96.4° to 112.8° and from 0.930 Å to 0.989 Å, respectively.
PB  - Royal Society of Chemistry
T2  - Physical Chemistry Chemical Physics
T1  - How flexible is the water molecule structure? Analysis of crystal structures and the potential energy surface
VL  - 22
IS  - 7
SP  - 4138
EP  - 4143
DO  - 10.1039/C9CP07042G
ER  - 

@article{
author = "Milovanović, Milan R. and Živković, Jelena M. and Ninković, Dragan and Stanković, Ivana M. and Zarić, Snežana D.",
year = "2020",
abstract = "Water molecules from crystal structures archived in the CSD show a relatively large range both in the bond angle and bond lengths. High level ab initio calculations at the CCSD(T)/CBS level predicted a possibility for energetically low-cost (±1 kcal mol−1) changes of the bond angle and bond lengths in a wide range, from 96.4° to 112.8° and from 0.930 Å to 0.989 Å, respectively.",
publisher = "Royal Society of Chemistry",
journal = "Physical Chemistry Chemical Physics",
title = "How flexible is the water molecule structure? Analysis of crystal structures and the potential energy surface",
volume = "22",
number = "7",
pages = "4138-4143",
doi = "10.1039/C9CP07042G"
}

Milovanović, M. R., Živković, J. M., Ninković, D., Stanković, I. M.,& Zarić, S. D.. (2020). How flexible is the water molecule structure? Analysis of crystal structures and the potential energy surface. in Physical Chemistry Chemical Physics
Royal Society of Chemistry., 22(7), 4138-4143.
https://doi.org/10.1039/C9CP07042G

Milovanović MR, Živković JM, Ninković D, Stanković IM, Zarić SD. How flexible is the water molecule structure? Analysis of crystal structures and the potential energy surface. in Physical Chemistry Chemical Physics. 2020;22(7):4138-4143.
doi:10.1039/C9CP07042G .

Milovanović, Milan R., Živković, Jelena M., Ninković, Dragan, Stanković, Ivana M., Zarić, Snežana D., "How flexible is the water molecule structure? Analysis of crystal structures and the potential energy surface" in Physical Chemistry Chemical Physics, 22, no. 7 (2020):4138-4143,
https://doi.org/10.1039/C9CP07042G . .

TY  - JOUR
AU  - Milovanović, Milan R.
AU  - Zarić, Snežana D.
AU  - Cornaton, Yann
AU  - Đukić, Jean-Pierre
PY  - 2020
UR  - https://cherry.chem.bg.ac.rs/handle/123456789/4267
AB  - The thermochemistry of the aminolysis of three methoxy Fischer carbenes, pentacarbonyl(phenylmethoxyalkylidene)chromium(0), molybdenum(0) and tungsten(0), was studied experimentally and theoretically with three amines, namely benzylamine, aniline and 3-pyrroline. Enthalpies of reactions were all determined by Isotherm Calorimetric Titration (ITC) in chlorobenzene at 298.15 K, which provided in almost all cases values of ΔrH larger than -15 kcal/mol suggesting energetically favourable transformations for all amines except aniline. No significant dependence of the enthalpy of reaction upon the nature of the metal atom of the carbene complex was found. Further ITC experiments confirmed the partial second-order reaction in amine. All COSMO-DFT computed enthalpies of reaction (spanning ca. -5.5 kcal/mol up to -20 kcal/mol) were found to be in excellent agreement with experimental values, while calculated Gibbs free energies suggested spontaneous processes for all reactions except the one with aniline.
PB  - Elsevier
T2  - Journal of Organometallic Chemistry
T1  - Joint Isotherm Calorimetric Titration–DFT Investigation of the Demethoxy-Amination of Fischer Carbenes
VL  - 929
SP  - 121582
DO  - 10.1016/j.jorganchem.2020.121582
ER  - 

@article{
author = "Milovanović, Milan R. and Zarić, Snežana D. and Cornaton, Yann and Đukić, Jean-Pierre",
year = "2020",
abstract = "The thermochemistry of the aminolysis of three methoxy Fischer carbenes, pentacarbonyl(phenylmethoxyalkylidene)chromium(0), molybdenum(0) and tungsten(0), was studied experimentally and theoretically with three amines, namely benzylamine, aniline and 3-pyrroline. Enthalpies of reactions were all determined by Isotherm Calorimetric Titration (ITC) in chlorobenzene at 298.15 K, which provided in almost all cases values of ΔrH larger than -15 kcal/mol suggesting energetically favourable transformations for all amines except aniline. No significant dependence of the enthalpy of reaction upon the nature of the metal atom of the carbene complex was found. Further ITC experiments confirmed the partial second-order reaction in amine. All COSMO-DFT computed enthalpies of reaction (spanning ca. -5.5 kcal/mol up to -20 kcal/mol) were found to be in excellent agreement with experimental values, while calculated Gibbs free energies suggested spontaneous processes for all reactions except the one with aniline.",
publisher = "Elsevier",
journal = "Journal of Organometallic Chemistry",
title = "Joint Isotherm Calorimetric Titration–DFT Investigation of the Demethoxy-Amination of Fischer Carbenes",
volume = "929",
pages = "121582",
doi = "10.1016/j.jorganchem.2020.121582"
}

Milovanović, M. R., Zarić, S. D., Cornaton, Y.,& Đukić, J.. (2020). Joint Isotherm Calorimetric Titration–DFT Investigation of the Demethoxy-Amination of Fischer Carbenes. in Journal of Organometallic Chemistry
Elsevier., 929, 121582.
https://doi.org/10.1016/j.jorganchem.2020.121582

Milovanović MR, Zarić SD, Cornaton Y, Đukić J. Joint Isotherm Calorimetric Titration–DFT Investigation of the Demethoxy-Amination of Fischer Carbenes. in Journal of Organometallic Chemistry. 2020;929:121582.
doi:10.1016/j.jorganchem.2020.121582 .

Milovanović, Milan R., Zarić, Snežana D., Cornaton, Yann, Đukić, Jean-Pierre, "Joint Isotherm Calorimetric Titration–DFT Investigation of the Demethoxy-Amination of Fischer Carbenes" in Journal of Organometallic Chemistry, 929 (2020):121582,
https://doi.org/10.1016/j.jorganchem.2020.121582 . .

TY  - JOUR
AU  - Milovanović, Milan R.
AU  - Dherbassy, Quentin
AU  - Wencel‐Delord, Joanna
AU  - Colobert, Françoise
AU  - Zarić, Snežana D.
AU  - Đukić, Jean-Pierre
PY  - 2020
UR  - https://cherry.chem.bg.ac.rs/handle/123456789/4337
AB  - To figure out the possible role of 1,1,1,3,3,3-hexafluoropropan-2-ol (HFIP) as well as to provide reference thermochemical data in solution, the formation of Lewis acid-base complexes between HFIP (Lewis acid) and a series of 8 different Lewis bases (3 sulfoxides, 3 Nsp2 pyridine derivatives, 1 aromatic amine, 1 cyclic aliphatic ether) was examined by isothermal titration calorimetry (ITC) experiments and static density functional theory augmented with Dispersion (DFT−D) calculations. Measured ITC association enthalpy values (ΔHa) lie between −9.3 and −14 kcal mol−1. Computations including a PCM implicit solvation model produced similar exothermicity of association of all studied systems compared to the ITC data with ΔHa values ranging from −8.5 to −12.7 kcal mol−1. An additional set of calculations combining implicit and explicit solvation by chlorobenzene of the reactants, pointed out the relatively low interference of the solvent with the HFIP-base complexation: its main effect is to slightly enhance the Gibbs energy of the HFIP-Lewis base association. It is speculated that the interactions of bulk HFIP with Lewis bases therefore may significantly intervene in catalytic processes not only via the dynamic microstructuring of the medium but also more explicitly by affecting bonds’ polarization at the Lewis bases.
PB  - Wiley
T2  - ChemPhysChem
T1  - The Affinity of Some Lewis Bases for Hexafluoroisopropanol as a Reference Lewis Acid: An ITC/DFT Study
VL  - 21
IS  - 18
SP  - 2136
EP  - 2142
DO  - 10.1002/cphc.202000560
ER  - 

@article{
author = "Milovanović, Milan R. and Dherbassy, Quentin and Wencel‐Delord, Joanna and Colobert, Françoise and Zarić, Snežana D. and Đukić, Jean-Pierre",
year = "2020",
abstract = "To figure out the possible role of 1,1,1,3,3,3-hexafluoropropan-2-ol (HFIP) as well as to provide reference thermochemical data in solution, the formation of Lewis acid-base complexes between HFIP (Lewis acid) and a series of 8 different Lewis bases (3 sulfoxides, 3 Nsp2 pyridine derivatives, 1 aromatic amine, 1 cyclic aliphatic ether) was examined by isothermal titration calorimetry (ITC) experiments and static density functional theory augmented with Dispersion (DFT−D) calculations. Measured ITC association enthalpy values (ΔHa) lie between −9.3 and −14 kcal mol−1. Computations including a PCM implicit solvation model produced similar exothermicity of association of all studied systems compared to the ITC data with ΔHa values ranging from −8.5 to −12.7 kcal mol−1. An additional set of calculations combining implicit and explicit solvation by chlorobenzene of the reactants, pointed out the relatively low interference of the solvent with the HFIP-base complexation: its main effect is to slightly enhance the Gibbs energy of the HFIP-Lewis base association. It is speculated that the interactions of bulk HFIP with Lewis bases therefore may significantly intervene in catalytic processes not only via the dynamic microstructuring of the medium but also more explicitly by affecting bonds’ polarization at the Lewis bases.",
publisher = "Wiley",
journal = "ChemPhysChem",
title = "The Affinity of Some Lewis Bases for Hexafluoroisopropanol as a Reference Lewis Acid: An ITC/DFT Study",
volume = "21",
number = "18",
pages = "2136-2142",
doi = "10.1002/cphc.202000560"
}

Milovanović, M. R., Dherbassy, Q., Wencel‐Delord, J., Colobert, F., Zarić, S. D.,& Đukić, J.. (2020). The Affinity of Some Lewis Bases for Hexafluoroisopropanol as a Reference Lewis Acid: An ITC/DFT Study. in ChemPhysChem
Wiley., 21(18), 2136-2142.
https://doi.org/10.1002/cphc.202000560

Milovanović MR, Dherbassy Q, Wencel‐Delord J, Colobert F, Zarić SD, Đukić J. The Affinity of Some Lewis Bases for Hexafluoroisopropanol as a Reference Lewis Acid: An ITC/DFT Study. in ChemPhysChem. 2020;21(18):2136-2142.
doi:10.1002/cphc.202000560 .

Milovanović, Milan R., Dherbassy, Quentin, Wencel‐Delord, Joanna, Colobert, Françoise, Zarić, Snežana D., Đukić, Jean-Pierre, "The Affinity of Some Lewis Bases for Hexafluoroisopropanol as a Reference Lewis Acid: An ITC/DFT Study" in ChemPhysChem, 21, no. 18 (2020):2136-2142,
https://doi.org/10.1002/cphc.202000560 . .

TY  - JOUR
AU  - Milovanović, Milan R.
AU  - Dherbassy, Quentin
AU  - Wencel‐Delord, Joanna
AU  - Colobert, Françoise
AU  - Zarić, Snežana D.
AU  - Đukić, Jean-Pierre
PY  - 2020
UR  - https://cherry.chem.bg.ac.rs/handle/123456789/4339
AB  - To figure out the possible role of 1,1,1,3,3,3-hexafluoropropan-2-ol (HFIP) as well as to provide reference thermochemical data in solution, the formation of Lewis acid-base complexes between HFIP (Lewis acid) and a series of 8 different Lewis bases (3 sulfoxides, 3 Nsp2 pyridine derivatives, 1 aromatic amine, 1 cyclic aliphatic ether) was examined by isothermal titration calorimetry (ITC) experiments and static density functional theory augmented with Dispersion (DFT−D) calculations. Measured ITC association enthalpy values (ΔHa) lie between −9.3 and −14 kcal mol−1. Computations including a PCM implicit solvation model produced similar exothermicity of association of all studied systems compared to the ITC data with ΔHa values ranging from −8.5 to −12.7 kcal mol−1. An additional set of calculations combining implicit and explicit solvation by chlorobenzene of the reactants, pointed out the relatively low interference of the solvent with the HFIP-base complexation: its main effect is to slightly enhance the Gibbs energy of the HFIP-Lewis base association. It is speculated that the interactions of bulk HFIP with Lewis bases therefore may significantly intervene in catalytic processes not only via the dynamic microstructuring of the medium but also more explicitly by affecting bonds’ polarization at the Lewis bases.
PB  - Wiley
T2  - ChemPhysChem
T1  - The Affinity of Some Lewis Bases for Hexafluoroisopropanol as a Reference Lewis Acid: An ITC/DFT Study
VL  - 21
IS  - 18
SP  - 2136
EP  - 2142
DO  - 10.1002/cphc.202000560
ER  - 

@article{
author = "Milovanović, Milan R. and Dherbassy, Quentin and Wencel‐Delord, Joanna and Colobert, Françoise and Zarić, Snežana D. and Đukić, Jean-Pierre",
year = "2020",
abstract = "To figure out the possible role of 1,1,1,3,3,3-hexafluoropropan-2-ol (HFIP) as well as to provide reference thermochemical data in solution, the formation of Lewis acid-base complexes between HFIP (Lewis acid) and a series of 8 different Lewis bases (3 sulfoxides, 3 Nsp2 pyridine derivatives, 1 aromatic amine, 1 cyclic aliphatic ether) was examined by isothermal titration calorimetry (ITC) experiments and static density functional theory augmented with Dispersion (DFT−D) calculations. Measured ITC association enthalpy values (ΔHa) lie between −9.3 and −14 kcal mol−1. Computations including a PCM implicit solvation model produced similar exothermicity of association of all studied systems compared to the ITC data with ΔHa values ranging from −8.5 to −12.7 kcal mol−1. An additional set of calculations combining implicit and explicit solvation by chlorobenzene of the reactants, pointed out the relatively low interference of the solvent with the HFIP-base complexation: its main effect is to slightly enhance the Gibbs energy of the HFIP-Lewis base association. It is speculated that the interactions of bulk HFIP with Lewis bases therefore may significantly intervene in catalytic processes not only via the dynamic microstructuring of the medium but also more explicitly by affecting bonds’ polarization at the Lewis bases.",
publisher = "Wiley",
journal = "ChemPhysChem",
title = "The Affinity of Some Lewis Bases for Hexafluoroisopropanol as a Reference Lewis Acid: An ITC/DFT Study",
volume = "21",
number = "18",
pages = "2136-2142",
doi = "10.1002/cphc.202000560"
}

Milovanović, M. R., Dherbassy, Q., Wencel‐Delord, J., Colobert, F., Zarić, S. D.,& Đukić, J.. (2020). The Affinity of Some Lewis Bases for Hexafluoroisopropanol as a Reference Lewis Acid: An ITC/DFT Study. in ChemPhysChem
Wiley., 21(18), 2136-2142.
https://doi.org/10.1002/cphc.202000560

Milovanović MR, Dherbassy Q, Wencel‐Delord J, Colobert F, Zarić SD, Đukić J. The Affinity of Some Lewis Bases for Hexafluoroisopropanol as a Reference Lewis Acid: An ITC/DFT Study. in ChemPhysChem. 2020;21(18):2136-2142.
doi:10.1002/cphc.202000560 .

Milovanović, Milan R., Dherbassy, Quentin, Wencel‐Delord, Joanna, Colobert, Françoise, Zarić, Snežana D., Đukić, Jean-Pierre, "The Affinity of Some Lewis Bases for Hexafluoroisopropanol as a Reference Lewis Acid: An ITC/DFT Study" in ChemPhysChem, 21, no. 18 (2020):2136-2142,
https://doi.org/10.1002/cphc.202000560 . .

TY  - DATA
AU  - Milovanović, Milan R.
AU  - Dherbassy, Quentin
AU  - Wencel‐Delord, Joanna
AU  - Colobert, Françoise
AU  - Zarić, Snežana D.
AU  - Đukić, Jean-Pierre
PY  - 2020
UR  - https://cherry.chem.bg.ac.rs/handle/123456789/4346
PB  - Wiley
T2  - ChemPhysChem
T1  - Supplementary data for the article: Milovanović, M. R.; Dherbassy, Q.; Wencel‐Delord, J.; Colobert, F.; Zarić, S. D.; Đukić, J.-P. The Affinity of Some Lewis Bases for Hexafluoroisopropanol as a Reference Lewis Acid: An ITC/DFT Study. ChemPhysChem 2020, 21 (18), 2136–2142. https://doi.org/10.1002/cphc.202000560.
VL  - 21
IS  - 18
SP  - 2136
EP  - 2142
UR  - https://hdl.handle.net/21.15107/rcub_cherry_4346
ER  - 

@misc{
author = "Milovanović, Milan R. and Dherbassy, Quentin and Wencel‐Delord, Joanna and Colobert, Françoise and Zarić, Snežana D. and Đukić, Jean-Pierre",
year = "2020",
publisher = "Wiley",
journal = "ChemPhysChem",
title = "Supplementary data for the article: Milovanović, M. R.; Dherbassy, Q.; Wencel‐Delord, J.; Colobert, F.; Zarić, S. D.; Đukić, J.-P. The Affinity of Some Lewis Bases for Hexafluoroisopropanol as a Reference Lewis Acid: An ITC/DFT Study. ChemPhysChem 2020, 21 (18), 2136–2142. https://doi.org/10.1002/cphc.202000560.",
volume = "21",
number = "18",
pages = "2136-2142",
url = "https://hdl.handle.net/21.15107/rcub_cherry_4346"
}

Milovanović, M. R., Dherbassy, Q., Wencel‐Delord, J., Colobert, F., Zarić, S. D.,& Đukić, J.. (2020). Supplementary data for the article: Milovanović, M. R.; Dherbassy, Q.; Wencel‐Delord, J.; Colobert, F.; Zarić, S. D.; Đukić, J.-P. The Affinity of Some Lewis Bases for Hexafluoroisopropanol as a Reference Lewis Acid: An ITC/DFT Study. ChemPhysChem 2020, 21 (18), 2136–2142. https://doi.org/10.1002/cphc.202000560.. in ChemPhysChem
Wiley., 21(18), 2136-2142.
https://hdl.handle.net/21.15107/rcub_cherry_4346

Milovanović MR, Dherbassy Q, Wencel‐Delord J, Colobert F, Zarić SD, Đukić J. Supplementary data for the article: Milovanović, M. R.; Dherbassy, Q.; Wencel‐Delord, J.; Colobert, F.; Zarić, S. D.; Đukić, J.-P. The Affinity of Some Lewis Bases for Hexafluoroisopropanol as a Reference Lewis Acid: An ITC/DFT Study. ChemPhysChem 2020, 21 (18), 2136–2142. https://doi.org/10.1002/cphc.202000560.. in ChemPhysChem. 2020;21(18):2136-2142.
https://hdl.handle.net/21.15107/rcub_cherry_4346 .

Milovanović, Milan R., Dherbassy, Quentin, Wencel‐Delord, Joanna, Colobert, Françoise, Zarić, Snežana D., Đukić, Jean-Pierre, "Supplementary data for the article: Milovanović, M. R.; Dherbassy, Q.; Wencel‐Delord, J.; Colobert, F.; Zarić, S. D.; Đukić, J.-P. The Affinity of Some Lewis Bases for Hexafluoroisopropanol as a Reference Lewis Acid: An ITC/DFT Study. ChemPhysChem 2020, 21 (18), 2136–2142. https://doi.org/10.1002/cphc.202000560." in ChemPhysChem, 21, no. 18 (2020):2136-2142,
https://hdl.handle.net/21.15107/rcub_cherry_4346 .

TY  - CONF
AU  - Milovanović, Milan R.
AU  - Živković, Jelena M.
AU  - Ninković, Dragan B.
AU  - Stanković, Ivana M.
AU  - Zarić, Snežana D.
PY  - 2019
UR  - https://icni2019.eventos.chemistry.pt/
UR  - http://cherry.chem.bg.ac.rs/handle/123456789/6358
AB  - Water molecule is ubiquitous in nature. Due to polar structure and ability for hydrogen bonding water molecule plays important role in many life processes as well as in packing of small molecules crystal structures. Over the past decades, the structure of water molecule [1] and water dimers [2] has been intensively studied. The experimental values for a free water molecule in the gas phase are the bond (O-H) length of 0.9572 ± 0.0003 Å and the bond angle (H-O-H) of 104.52 ± 0.05⁰. [3] Calculations have showed that equilibrium structure of water molecule has the bond length of 0.95785 ± 0.00005 Å and the bond angle of 104.501± 0.005⁰. [4] Energy of hydrogen bonded water dimer predicted by theory is -4.77 kcal/mol. [5] In this study, we performed an analysis of non-coordinated water containing structures archived in Cambridge Structural Database (CSD) as well as ab-initio calculations on a range of bond angles and bond lengths of water molecule and water dimers. We analyzed different geometrical parameters. The results of analysis of crystal structures showed that there is a large discrepancy of both the bond length and the bond angle values form the ideal ones. For example, the range of the bond angles of X-ray solved structures having R factor ≤ 0.05 is 22.43⁰-180.00⁰, while reliable bond angles predicted by calculations are in the range of ca. 93.2⁰-116.4⁰. Consequently, it would lead to at least 15% of X-ray solved structures that contain questionable water molecule geometries. Calculations on hydrogen bond potential energy surface were compared with the analysis of the all hydrogen bonds of non-coordinated water molecules in the CSD. We were able to correlate the calculated data with two regions of hydrogen bonded water dimers found in the CSD.
C3  - 1st International Conferences on Noncovalent Interactions (ICNI-2019), Lisbon, Portugal, 2-6 September, 2019
T1  - Structure of water molecule and water hydrogen bonding: joint Cambridge Structural Database and ab-initio calculations study.
UR  - https://hdl.handle.net/21.15107/rcub_cherry_6358
ER  - 

@conference{
author = "Milovanović, Milan R. and Živković, Jelena M. and Ninković, Dragan B. and Stanković, Ivana M. and Zarić, Snežana D.",
year = "2019",
abstract = "Water molecule is ubiquitous in nature. Due to polar structure and ability for hydrogen bonding water molecule plays important role in many life processes as well as in packing of small molecules crystal structures. Over the past decades, the structure of water molecule [1] and water dimers [2] has been intensively studied. The experimental values for a free water molecule in the gas phase are the bond (O-H) length of 0.9572 ± 0.0003 Å and the bond angle (H-O-H) of 104.52 ± 0.05⁰. [3] Calculations have showed that equilibrium structure of water molecule has the bond length of 0.95785 ± 0.00005 Å and the bond angle of 104.501± 0.005⁰. [4] Energy of hydrogen bonded water dimer predicted by theory is -4.77 kcal/mol. [5] In this study, we performed an analysis of non-coordinated water containing structures archived in Cambridge Structural Database (CSD) as well as ab-initio calculations on a range of bond angles and bond lengths of water molecule and water dimers. We analyzed different geometrical parameters. The results of analysis of crystal structures showed that there is a large discrepancy of both the bond length and the bond angle values form the ideal ones. For example, the range of the bond angles of X-ray solved structures having R factor ≤ 0.05 is 22.43⁰-180.00⁰, while reliable bond angles predicted by calculations are in the range of ca. 93.2⁰-116.4⁰. Consequently, it would lead to at least 15% of X-ray solved structures that contain questionable water molecule geometries. Calculations on hydrogen bond potential energy surface were compared with the analysis of the all hydrogen bonds of non-coordinated water molecules in the CSD. We were able to correlate the calculated data with two regions of hydrogen bonded water dimers found in the CSD.",
journal = "1st International Conferences on Noncovalent Interactions (ICNI-2019), Lisbon, Portugal, 2-6 September, 2019",
title = "Structure of water molecule and water hydrogen bonding: joint Cambridge Structural Database and ab-initio calculations study.",
url = "https://hdl.handle.net/21.15107/rcub_cherry_6358"
}

Milovanović, M. R., Živković, J. M., Ninković, D. B., Stanković, I. M.,& Zarić, S. D.. (2019). Structure of water molecule and water hydrogen bonding: joint Cambridge Structural Database and ab-initio calculations study.. in 1st International Conferences on Noncovalent Interactions (ICNI-2019), Lisbon, Portugal, 2-6 September, 2019.
https://hdl.handle.net/21.15107/rcub_cherry_6358

Milovanović MR, Živković JM, Ninković DB, Stanković IM, Zarić SD. Structure of water molecule and water hydrogen bonding: joint Cambridge Structural Database and ab-initio calculations study.. in 1st International Conferences on Noncovalent Interactions (ICNI-2019), Lisbon, Portugal, 2-6 September, 2019. 2019;.
https://hdl.handle.net/21.15107/rcub_cherry_6358 .

Milovanović, Milan R., Živković, Jelena M., Ninković, Dragan B., Stanković, Ivana M., Zarić, Snežana D., "Structure of water molecule and water hydrogen bonding: joint Cambridge Structural Database and ab-initio calculations study." in 1st International Conferences on Noncovalent Interactions (ICNI-2019), Lisbon, Portugal, 2-6 September, 2019 (2019),
https://hdl.handle.net/21.15107/rcub_cherry_6358 .

TY  - CONF
AU  - Milovanović, Milan R.
AU  - Živković, Jelena M.
AU  - Ninković, Dragan B.
AU  - Stanković, Ivana M.
AU  - Zarić, Snežana D.
PY  - 2019
UR  - http://cherry.chem.bg.ac.rs/handle/123456789/6359
AB  - Water molecule is omnipresent in nature. Due to polar structure and ability for hydrogen bonding water molecule plays important role in many life processes as well as in packing of small molecules crystal structures. Over the past decades, the structure of water molecule has been intensively studied [1,2]. It has been found that a free water molecule in gas phase has the bond angle (H–O–H) of 104.52 ± 0.05° [3], while the bond angle of crystalline hydrates from over 40 structures solved by neutron diffraction analysis is in range from 102.50° to 115.25° [4]. Spectroscopic potential energy surface based calculations showed that equilibrium structure of water molecule has the bond angle of 104.501°± 0.005 [5].
In this study, we performed an analysis of water containing structures archived in Cambridge Structural Database (CSD) as well as ab-initio calculations on a range of bond angles of water molecule. 
Results of analysis of structures solved by neutron as well as by X-ray diffraction analysis with R factor ≤ 0.1 showed that there is a large discrepancy of the bond angle values from the ideal one(s). Namely, the range of the bond angle in neutron solved structures is 79.76–141.64° while in X-ray solved structures is 17.03–180.00°. By calculating the energy protentional curve of the bond angle change it is shown the bond angles beyond the range of ca. 93.0–116.0° are rather doubtful. Accordingly, it would lead to at least 15% of X-ray solved structures that contain questionable water molecule geometries.
PB  - Belgrade : Serbian Crystallographic Society
C3  - 26th Conference of the Serbian Crystallographic Society, June 27–28rd, 2019 Silver lake, Serbia
T1  - Are the bond angles of water molecules in crystal structures reliable? Joint cambridge structural database and ab-initio calculation analysis
SP  - 34
EP  - 35
UR  - https://hdl.handle.net/21.15107/rcub_cherry_6359
ER  - 

@conference{
author = "Milovanović, Milan R. and Živković, Jelena M. and Ninković, Dragan B. and Stanković, Ivana M. and Zarić, Snežana D.",
year = "2019",
abstract = "Water molecule is omnipresent in nature. Due to polar structure and ability for hydrogen bonding water molecule plays important role in many life processes as well as in packing of small molecules crystal structures. Over the past decades, the structure of water molecule has been intensively studied [1,2]. It has been found that a free water molecule in gas phase has the bond angle (H–O–H) of 104.52 ± 0.05° [3], while the bond angle of crystalline hydrates from over 40 structures solved by neutron diffraction analysis is in range from 102.50° to 115.25° [4]. Spectroscopic potential energy surface based calculations showed that equilibrium structure of water molecule has the bond angle of 104.501°± 0.005 [5].
In this study, we performed an analysis of water containing structures archived in Cambridge Structural Database (CSD) as well as ab-initio calculations on a range of bond angles of water molecule. 
Results of analysis of structures solved by neutron as well as by X-ray diffraction analysis with R factor ≤ 0.1 showed that there is a large discrepancy of the bond angle values from the ideal one(s). Namely, the range of the bond angle in neutron solved structures is 79.76–141.64° while in X-ray solved structures is 17.03–180.00°. By calculating the energy protentional curve of the bond angle change it is shown the bond angles beyond the range of ca. 93.0–116.0° are rather doubtful. Accordingly, it would lead to at least 15% of X-ray solved structures that contain questionable water molecule geometries.",
publisher = "Belgrade : Serbian Crystallographic Society",
journal = "26th Conference of the Serbian Crystallographic Society, June 27–28rd, 2019 Silver lake, Serbia",
title = "Are the bond angles of water molecules in crystal structures reliable? Joint cambridge structural database and ab-initio calculation analysis",
pages = "34-35",
url = "https://hdl.handle.net/21.15107/rcub_cherry_6359"
}

Milovanović, M. R., Živković, J. M., Ninković, D. B., Stanković, I. M.,& Zarić, S. D.. (2019). Are the bond angles of water molecules in crystal structures reliable? Joint cambridge structural database and ab-initio calculation analysis. in 26th Conference of the Serbian Crystallographic Society, June 27–28rd, 2019 Silver lake, Serbia
Belgrade : Serbian Crystallographic Society., 34-35.
https://hdl.handle.net/21.15107/rcub_cherry_6359

Milovanović MR, Živković JM, Ninković DB, Stanković IM, Zarić SD. Are the bond angles of water molecules in crystal structures reliable? Joint cambridge structural database and ab-initio calculation analysis. in 26th Conference of the Serbian Crystallographic Society, June 27–28rd, 2019 Silver lake, Serbia. 2019;:34-35.
https://hdl.handle.net/21.15107/rcub_cherry_6359 .

Milovanović, Milan R., Živković, Jelena M., Ninković, Dragan B., Stanković, Ivana M., Zarić, Snežana D., "Are the bond angles of water molecules in crystal structures reliable? Joint cambridge structural database and ab-initio calculation analysis" in 26th Conference of the Serbian Crystallographic Society, June 27–28rd, 2019 Silver lake, Serbia (2019):34-35,
https://hdl.handle.net/21.15107/rcub_cherry_6359 .