TY  - JOUR
AU  - Blagojević Filipović, Jelena P.
AU  - Vojislavljević-Vasilev, Dubravka Z.
AU  - Zarić, Snežana D.
PY  - 2024
UR  - http://cherry.chem.bg.ac.rs/handle/123456789/6457
AB  - Interactions of coordinated ammonia and C6-aromatic rings were studied by analyzing crystal structures in the Cambridge Structural Database (CSD) and by quantum chemical calculations. Interactions between coordinated ammonia and C6-aromatic rings in the crystal structures from the CSD can have one, two, or three ammine ligands interacting with the aromatic ring, while the most frequent are the interactions with one interacting ammine ligand. The distance between coordinated ammonia and the aromatic ring is significantly influenced by charges of the species; the shortest distances were observed for interactions with oppositely charged species. The interaction energies were calculated in model systems between the benzene molecule and coordinated ammonia in metal ammine complexes. In the calculations, we studied the influence of the number of interacting ammine ligands, the complex charge, the metal atom size and the coordination number on the strength of the interactions. The results show that the interaction strength increases with an increasing number of interacting ammine ligands, with an increasing complex charge and with a decreasing metal atom size and the coordination number in the ammine complex. For example, the interaction between the [Co(NH3)6]3+ complex and benzene is the weakest in the case of one interacting ammine ligand (−30.82 kcal/mol), stronger in the case of two interacting ammine ligands (−33.61 kcal/mol), and the strongest in the case of three interacting ligands (−34.16 kcal/mol). For metal complexes with charges +1, +2, and +3, the calculated interaction energies with one interacting ammine ligand can be as strong as −10.51, −15.75, and −30.82 kcal/mol. Complexes [Ni(NH3)6]2+ and [Cd(NH3)6]2+ differ by the metal atom size. The interaction is stronger in the case of the smaller [Ni(NH3)6]2+ complex (−15.75 kcal/mol) compared to the larger [Cd(NH3)6]2+ complex (−12.94 kcal/mol). In addition, complexes with coordination number four form stronger interactions than complexes with coordination number six. In the cases with two interacting ammine ligands, the interacting energy in the [Pt(NH3)4]2+/benzene system is −22.09 kcal/mol, while in the [Cd(NH3)6]2+/benzene system, it is −14.93 kcal/mol.
PB  - American Chemical Society
T2  - Crystal Growth & Design
T1  - Crystallographic and Quantum Chemical Study of NH/π Interactions of Metal Ammine Complexes with Aromatic Rings in the Second Coordination Sphere
VL  - 24
IS  - 4
SP  - 1705
EP  - 1714
DO  - 10.1021/acs.cgd.3c01346
ER  - 

@article{
author = "Blagojević Filipović, Jelena P. and Vojislavljević-Vasilev, Dubravka Z. and Zarić, Snežana D.",
year = "2024",
abstract = "Interactions of coordinated ammonia and C6-aromatic rings were studied by analyzing crystal structures in the Cambridge Structural Database (CSD) and by quantum chemical calculations. Interactions between coordinated ammonia and C6-aromatic rings in the crystal structures from the CSD can have one, two, or three ammine ligands interacting with the aromatic ring, while the most frequent are the interactions with one interacting ammine ligand. The distance between coordinated ammonia and the aromatic ring is significantly influenced by charges of the species; the shortest distances were observed for interactions with oppositely charged species. The interaction energies were calculated in model systems between the benzene molecule and coordinated ammonia in metal ammine complexes. In the calculations, we studied the influence of the number of interacting ammine ligands, the complex charge, the metal atom size and the coordination number on the strength of the interactions. The results show that the interaction strength increases with an increasing number of interacting ammine ligands, with an increasing complex charge and with a decreasing metal atom size and the coordination number in the ammine complex. For example, the interaction between the [Co(NH3)6]3+ complex and benzene is the weakest in the case of one interacting ammine ligand (−30.82 kcal/mol), stronger in the case of two interacting ammine ligands (−33.61 kcal/mol), and the strongest in the case of three interacting ligands (−34.16 kcal/mol). For metal complexes with charges +1, +2, and +3, the calculated interaction energies with one interacting ammine ligand can be as strong as −10.51, −15.75, and −30.82 kcal/mol. Complexes [Ni(NH3)6]2+ and [Cd(NH3)6]2+ differ by the metal atom size. The interaction is stronger in the case of the smaller [Ni(NH3)6]2+ complex (−15.75 kcal/mol) compared to the larger [Cd(NH3)6]2+ complex (−12.94 kcal/mol). In addition, complexes with coordination number four form stronger interactions than complexes with coordination number six. In the cases with two interacting ammine ligands, the interacting energy in the [Pt(NH3)4]2+/benzene system is −22.09 kcal/mol, while in the [Cd(NH3)6]2+/benzene system, it is −14.93 kcal/mol.",
publisher = "American Chemical Society",
journal = "Crystal Growth & Design",
title = "Crystallographic and Quantum Chemical Study of NH/π Interactions of Metal Ammine Complexes with Aromatic Rings in the Second Coordination Sphere",
volume = "24",
number = "4",
pages = "1705-1714",
doi = "10.1021/acs.cgd.3c01346"
}

Blagojević Filipović, J. P., Vojislavljević-Vasilev, D. Z.,& Zarić, S. D.. (2024). Crystallographic and Quantum Chemical Study of NH/π Interactions of Metal Ammine Complexes with Aromatic Rings in the Second Coordination Sphere. in Crystal Growth & Design
American Chemical Society., 24(4), 1705-1714.
https://doi.org/10.1021/acs.cgd.3c01346

Blagojević Filipović JP, Vojislavljević-Vasilev DZ, Zarić SD. Crystallographic and Quantum Chemical Study of NH/π Interactions of Metal Ammine Complexes with Aromatic Rings in the Second Coordination Sphere. in Crystal Growth & Design. 2024;24(4):1705-1714.
doi:10.1021/acs.cgd.3c01346 .

Blagojević Filipović, Jelena P., Vojislavljević-Vasilev, Dubravka Z., Zarić, Snežana D., "Crystallographic and Quantum Chemical Study of NH/π Interactions of Metal Ammine Complexes with Aromatic Rings in the Second Coordination Sphere" in Crystal Growth & Design, 24, no. 4 (2024):1705-1714,
https://doi.org/10.1021/acs.cgd.3c01346 . .

TY  - CONF
AU  - Blagojević Filipović, Jelena P.
AU  - Ninković, Dragan B.
AU  - Zarić, Snežana D.
PY  - 2023
UR  - http://cherry.chem.bg.ac.rs/handle/123456789/6343
AB  - Noncovalent interactions at large distances play important role in molecular recognition processes, early steps of protein folding or design of supramolecular structures. Plateaus or even shallow minima can occur at potential energy curves of stacking interactions between certain ring types. Stacking interactions at large horizontal displacements are also frequently found in crystal structures of various rings. In this work we discuss how the horizontal displacement affects stacking interactions on the basis of interaction energy calculations and energy decomposition analysis performed by Symmetry-Adapted Perturbation Theory (SAPT). We compared aromatic/aromatic to aromatic/aliphatic stacking as well as stacking interactions involving resonance-assisted hydrogen bridged (RAHB) rings, including RAHB/RAHB and RAHB/aromatic interactions. Among RAHB rings we observed different behavior of polar and nonpolar RAHB molecules. A comparison of aromatic/aromatic and aromatic/aliphatic systems provides an insight into fundamental differences in the nature between these two interaction types, while comparing stacking involving RAHB rings we can observe difference between polar and nonpolar RAHB rings.
C3  - 2nd International Conference on Chemo and Bioinformatics (ICCBIKG_2023), Book of Proceedings, 28-29 September 2023, Kragujevac, Serbia, 2023
T1  - Stacking Interactions at Large Horizontal Displacements—Comparison of Various Ring Types
SP  - 645
EP  - 648
DO  - 10.46793/ICCBI23.645BF
UR  - https://hdl.handle.net/21.15107/rcub_cherry_6343
ER  - 

@conference{
author = "Blagojević Filipović, Jelena P. and Ninković, Dragan B. and Zarić, Snežana D.",
year = "2023",
abstract = "Noncovalent interactions at large distances play important role in molecular recognition processes, early steps of protein folding or design of supramolecular structures. Plateaus or even shallow minima can occur at potential energy curves of stacking interactions between certain ring types. Stacking interactions at large horizontal displacements are also frequently found in crystal structures of various rings. In this work we discuss how the horizontal displacement affects stacking interactions on the basis of interaction energy calculations and energy decomposition analysis performed by Symmetry-Adapted Perturbation Theory (SAPT). We compared aromatic/aromatic to aromatic/aliphatic stacking as well as stacking interactions involving resonance-assisted hydrogen bridged (RAHB) rings, including RAHB/RAHB and RAHB/aromatic interactions. Among RAHB rings we observed different behavior of polar and nonpolar RAHB molecules. A comparison of aromatic/aromatic and aromatic/aliphatic systems provides an insight into fundamental differences in the nature between these two interaction types, while comparing stacking involving RAHB rings we can observe difference between polar and nonpolar RAHB rings.",
journal = "2nd International Conference on Chemo and Bioinformatics (ICCBIKG_2023), Book of Proceedings, 28-29 September 2023, Kragujevac, Serbia, 2023",
title = "Stacking Interactions at Large Horizontal Displacements—Comparison of Various Ring Types",
pages = "645-648",
doi = "10.46793/ICCBI23.645BF",
url = "https://hdl.handle.net/21.15107/rcub_cherry_6343"
}

Blagojević Filipović, J. P., Ninković, D. B.,& Zarić, S. D.. (2023). Stacking Interactions at Large Horizontal Displacements—Comparison of Various Ring Types. in 2nd International Conference on Chemo and Bioinformatics (ICCBIKG_2023), Book of Proceedings, 28-29 September 2023, Kragujevac, Serbia, 2023, 645-648.
https://doi.org/10.46793/ICCBI23.645BF
https://hdl.handle.net/21.15107/rcub_cherry_6343

Blagojević Filipović JP, Ninković DB, Zarić SD. Stacking Interactions at Large Horizontal Displacements—Comparison of Various Ring Types. in 2nd International Conference on Chemo and Bioinformatics (ICCBIKG_2023), Book of Proceedings, 28-29 September 2023, Kragujevac, Serbia, 2023. 2023;:645-648.
doi:10.46793/ICCBI23.645BF
https://hdl.handle.net/21.15107/rcub_cherry_6343 .

Blagojević Filipović, Jelena P., Ninković, Dragan B., Zarić, Snežana D., "Stacking Interactions at Large Horizontal Displacements—Comparison of Various Ring Types" in 2nd International Conference on Chemo and Bioinformatics (ICCBIKG_2023), Book of Proceedings, 28-29 September 2023, Kragujevac, Serbia, 2023 (2023):645-648,
https://doi.org/10.46793/ICCBI23.645BF .,
https://hdl.handle.net/21.15107/rcub_cherry_6343 .

TY  - CONF
AU  - Blagojević Filipović, Jelena P.
AU  - Vojislavljević-Vasilev, Dubravka
AU  - Zarić, Snežana D.
PY  - 2023
UR  - http://cherry.chem.bg.ac.rs/handle/123456789/6344
AB  - The interactions of noncoordinated water or ammonia molecules with aromatic rings, as well as coordintaed water or coordinated ammonia molecules with aromatic rings have been investigated by searching the Cambridge Structural Database (CSD) and through quantum-chemical calculations. The data from the CSD show that for noncoordinated systems distances between the interacting fragments are the shortest in case of negative C6-aromatic groups and the longest in case of positive C6-aromatic groups. In case of contacts between coordinated water or ammonia molecules and C6-aromatic group, oppositely charged fragments are mutually closer than the neutral fragments. The DFT calculations for the water/benzene system yield an interaction energy of -2.97 kcal/mol, while for the [Zn(H2O)6]2+/C6H6 system the interaction energy is -14.72 kcal/mol. For the ammonia/benzene system, the DFT calculations yield an interaction energy of -2.28 kcal/mol, while for the [Zn(NH3)6]2+/C6H6 system it is -15.50 kcal/mol. The results show that there is an influence of water or ammonia coordination on OH/π or NH/π interactions; the interactions of coordinated species are significantly stronger. OH/π and NH/π interactions are comparable in both cases. OH/π interactions are slightly stronger than NH/π interactions in case of noncoordinated molecules due to higher partially positive charge on hydrogen atom of the water molecule, but this is not necessarily the case for the coordinated molecules due to additional interactions that can occur between the benzene ring and the other ligands present in the complex.
C3  - 2nd International Conference on Chemo and Bioinformatics (ICCBIKG_2023), Book of Proceedings, 28-29 September 2023, Kragujevac, Serbia, 2023
T1  - Influence of Coordination on OH/π and NH/π Interactions
DO  - 10.46793/ICCBI23.649BF
ER  - 

@conference{
author = "Blagojević Filipović, Jelena P. and Vojislavljević-Vasilev, Dubravka and Zarić, Snežana D.",
year = "2023",
abstract = "The interactions of noncoordinated water or ammonia molecules with aromatic rings, as well as coordintaed water or coordinated ammonia molecules with aromatic rings have been investigated by searching the Cambridge Structural Database (CSD) and through quantum-chemical calculations. The data from the CSD show that for noncoordinated systems distances between the interacting fragments are the shortest in case of negative C6-aromatic groups and the longest in case of positive C6-aromatic groups. In case of contacts between coordinated water or ammonia molecules and C6-aromatic group, oppositely charged fragments are mutually closer than the neutral fragments. The DFT calculations for the water/benzene system yield an interaction energy of -2.97 kcal/mol, while for the [Zn(H2O)6]2+/C6H6 system the interaction energy is -14.72 kcal/mol. For the ammonia/benzene system, the DFT calculations yield an interaction energy of -2.28 kcal/mol, while for the [Zn(NH3)6]2+/C6H6 system it is -15.50 kcal/mol. The results show that there is an influence of water or ammonia coordination on OH/π or NH/π interactions; the interactions of coordinated species are significantly stronger. OH/π and NH/π interactions are comparable in both cases. OH/π interactions are slightly stronger than NH/π interactions in case of noncoordinated molecules due to higher partially positive charge on hydrogen atom of the water molecule, but this is not necessarily the case for the coordinated molecules due to additional interactions that can occur between the benzene ring and the other ligands present in the complex.",
journal = "2nd International Conference on Chemo and Bioinformatics (ICCBIKG_2023), Book of Proceedings, 28-29 September 2023, Kragujevac, Serbia, 2023",
title = "Influence of Coordination on OH/π and NH/π Interactions",
doi = "10.46793/ICCBI23.649BF"
}

Blagojević Filipović, J. P., Vojislavljević-Vasilev, D.,& Zarić, S. D.. (2023). Influence of Coordination on OH/π and NH/π Interactions. in 2nd International Conference on Chemo and Bioinformatics (ICCBIKG_2023), Book of Proceedings, 28-29 September 2023, Kragujevac, Serbia, 2023.
https://doi.org/10.46793/ICCBI23.649BF

Blagojević Filipović JP, Vojislavljević-Vasilev D, Zarić SD. Influence of Coordination on OH/π and NH/π Interactions. in 2nd International Conference on Chemo and Bioinformatics (ICCBIKG_2023), Book of Proceedings, 28-29 September 2023, Kragujevac, Serbia, 2023. 2023;.
doi:10.46793/ICCBI23.649BF .

Blagojević Filipović, Jelena P., Vojislavljević-Vasilev, Dubravka, Zarić, Snežana D., "Influence of Coordination on OH/π and NH/π Interactions" in 2nd International Conference on Chemo and Bioinformatics (ICCBIKG_2023), Book of Proceedings, 28-29 September 2023, Kragujevac, Serbia, 2023 (2023),
https://doi.org/10.46793/ICCBI23.649BF . .

TY  - CONF
AU  - Malenov, Dušan P.
AU  - Blagojević Filipović, Jelena P.
AU  - Zarić, Snežana D.
PY  - 2023
UR  - http://cherry.chem.bg.ac.rs/handle/123456789/6345
AB  - The effects of alkyl substituents on stacking interactions of aromatic ligands in organometallic compounds were studied on two most common ligands with substituents pentamethylcyclopentadienyl (Cp*) and 1-methyl-4-isopropylbenzene (p-cymene). The analysis ofgeometries of interactions found in crystal structures deposited in the Cambridge Structural Database indicated that substituents are involved in interactions with aromatic rings, indicating the combination of stacking and C-and p-cymene ligands. Quantum chemical calculations on p-cymene half-sandwich ruthenium(II) compound showed that additional CB97D2/def2-TZVP interaction energy between two p-cymenecomplexes is -7.56 kcal/mol, while the interaction energy between two corresponding benzene complexes is -3.93 kcal/mol. Ruthenium p-cymene complexes can engage in stacking interactions with large horizontal displacements combined with interactions between the substituents, with a significant interaction energy of -4.57 kcal/mol. These studies show that substituents strengthen stacking interactions of coordinated aromatic rings and modulate their geometries by providing additional simultaneous interactions.
C3  - 2nd International Conference on Chemo and Bioinformatics (ICCBIKG_2023), Book of Proceedings, 28-29 September 2023, Kragujevac, Serbia, 2023
T1  - Substituent effects on stacking interactions of aromatic ligands in organometallic compounds – chemoinformatics and quantum chemical study
SP  - 625
EP  - 628
DO  - 10.46793/ICCBI23.625M
ER  - 

@conference{
author = "Malenov, Dušan P. and Blagojević Filipović, Jelena P. and Zarić, Snežana D.",
year = "2023",
abstract = "The effects of alkyl substituents on stacking interactions of aromatic ligands in organometallic compounds were studied on two most common ligands with substituents pentamethylcyclopentadienyl (Cp*) and 1-methyl-4-isopropylbenzene (p-cymene). The analysis ofgeometries of interactions found in crystal structures deposited in the Cambridge Structural Database indicated that substituents are involved in interactions with aromatic rings, indicating the combination of stacking and C-and p-cymene ligands. Quantum chemical calculations on p-cymene half-sandwich ruthenium(II) compound showed that additional CB97D2/def2-TZVP interaction energy between two p-cymenecomplexes is -7.56 kcal/mol, while the interaction energy between two corresponding benzene complexes is -3.93 kcal/mol. Ruthenium p-cymene complexes can engage in stacking interactions with large horizontal displacements combined with interactions between the substituents, with a significant interaction energy of -4.57 kcal/mol. These studies show that substituents strengthen stacking interactions of coordinated aromatic rings and modulate their geometries by providing additional simultaneous interactions.",
journal = "2nd International Conference on Chemo and Bioinformatics (ICCBIKG_2023), Book of Proceedings, 28-29 September 2023, Kragujevac, Serbia, 2023",
title = "Substituent effects on stacking interactions of aromatic ligands in organometallic compounds – chemoinformatics and quantum chemical study",
pages = "625-628",
doi = "10.46793/ICCBI23.625M"
}

Malenov, D. P., Blagojević Filipović, J. P.,& Zarić, S. D.. (2023). Substituent effects on stacking interactions of aromatic ligands in organometallic compounds – chemoinformatics and quantum chemical study. in 2nd International Conference on Chemo and Bioinformatics (ICCBIKG_2023), Book of Proceedings, 28-29 September 2023, Kragujevac, Serbia, 2023, 625-628.
https://doi.org/10.46793/ICCBI23.625M

Malenov DP, Blagojević Filipović JP, Zarić SD. Substituent effects on stacking interactions of aromatic ligands in organometallic compounds – chemoinformatics and quantum chemical study. in 2nd International Conference on Chemo and Bioinformatics (ICCBIKG_2023), Book of Proceedings, 28-29 September 2023, Kragujevac, Serbia, 2023. 2023;:625-628.
doi:10.46793/ICCBI23.625M .

Malenov, Dušan P., Blagojević Filipović, Jelena P., Zarić, Snežana D., "Substituent effects on stacking interactions of aromatic ligands in organometallic compounds – chemoinformatics and quantum chemical study" in 2nd International Conference on Chemo and Bioinformatics (ICCBIKG_2023), Book of Proceedings, 28-29 September 2023, Kragujevac, Serbia, 2023 (2023):625-628,
https://doi.org/10.46793/ICCBI23.625M . .

TY  - CONF
AU  - Blagojević Filipović, Jelena P.
AU  - Zarić, Snežana D.
PY  - 2023
UR  - http://cherry.chem.bg.ac.rs/handle/123456789/6404
AB  - Resonance-assisted hydrogen-bridged rings (RAHB) are promising structures in material design due to synergistic effects between hydrogen bonding and resonance. We investigated mutual contacts between RAHB ring structures deposited in the Cambridge Structural Database (CSD), as well as contacts between RAHB rings and C6-aromatic fragments. Stacking interactions in crystal structures are identified by parallel alignment of interacting fragments and a characteristic distance between the planes of the interacting fragments, which is between 3.0 and 4.0 Å. The existence of stacking interactions is then confirmed by quantum chemical calculations of interaction energies at dimer model systems. Namely, more than 90% of mutual RAHB/RAHB contacts found in the CSD are parallel and anti oriented. A smaller part of RAHB/C6-aromatic contacts (around 60%) is in parallel orientation. Both RAHB/RAHB and RAHB/C6-aromatic contacts typically form parallel layers at a specific distance (between 3.0 and 4.0 Å), which distinguishes them from benzene/benzene parallel contacts found in the CSD, where layers are not formed. The most abundant RAHB ring types found in the CSD are used as model systems for quantum chemical calculations of interaction energies. Malonaldehyde (H4C3O2), its mononitrigen analogue (H5C3NO) and dinitrogen analogue (H4C2N2O) are used as model systems for RAHB rings, while benzene molecule is used as a model system for a C6-aromatic fragment. RAHB/RAHB interactions can be quite strong (up to -4.7 kcal/mol in case of H5C3NO/H5C3NO dimer). RAHB/benzene interactions are generally weaker (up to -3.5 kcal/mol in case of H4C3O2/benzene dimer), but they can be also stronger than the corresponding RAHB/RAHB interactions, depending on the system. Both RAHB/RAHB and RAHB/benzene interactions are stronger than benzene/benzene stacking interactions (-2.7 kcal/mol). Stacking interactions can remain strong in some systems even when placed to large horizontal displacements. For example, benzene/benzene stacking preserves 70% of its maximum strength upon shifting to the displacement of 5.0 Å. Stacking interactions of RAHB rings can, in some cases, preserve similar portion of their strength (around 70%) at large displacements.
C3  - VIII International Congress “Engineering, Environment and Materials in Process Industry“
T1  - Resonance-Assisted Hydrogen-Bridged Rings: Parallel Alignment in Crystal Structures and Significant Noncovalent Attraction
UR  - https://hdl.handle.net/21.15107/rcub_cherry_6404
ER  - 

@conference{
author = "Blagojević Filipović, Jelena P. and Zarić, Snežana D.",
year = "2023",
abstract = "Resonance-assisted hydrogen-bridged rings (RAHB) are promising structures in material design due to synergistic effects between hydrogen bonding and resonance. We investigated mutual contacts between RAHB ring structures deposited in the Cambridge Structural Database (CSD), as well as contacts between RAHB rings and C6-aromatic fragments. Stacking interactions in crystal structures are identified by parallel alignment of interacting fragments and a characteristic distance between the planes of the interacting fragments, which is between 3.0 and 4.0 Å. The existence of stacking interactions is then confirmed by quantum chemical calculations of interaction energies at dimer model systems. Namely, more than 90% of mutual RAHB/RAHB contacts found in the CSD are parallel and anti oriented. A smaller part of RAHB/C6-aromatic contacts (around 60%) is in parallel orientation. Both RAHB/RAHB and RAHB/C6-aromatic contacts typically form parallel layers at a specific distance (between 3.0 and 4.0 Å), which distinguishes them from benzene/benzene parallel contacts found in the CSD, where layers are not formed. The most abundant RAHB ring types found in the CSD are used as model systems for quantum chemical calculations of interaction energies. Malonaldehyde (H4C3O2), its mononitrigen analogue (H5C3NO) and dinitrogen analogue (H4C2N2O) are used as model systems for RAHB rings, while benzene molecule is used as a model system for a C6-aromatic fragment. RAHB/RAHB interactions can be quite strong (up to -4.7 kcal/mol in case of H5C3NO/H5C3NO dimer). RAHB/benzene interactions are generally weaker (up to -3.5 kcal/mol in case of H4C3O2/benzene dimer), but they can be also stronger than the corresponding RAHB/RAHB interactions, depending on the system. Both RAHB/RAHB and RAHB/benzene interactions are stronger than benzene/benzene stacking interactions (-2.7 kcal/mol). Stacking interactions can remain strong in some systems even when placed to large horizontal displacements. For example, benzene/benzene stacking preserves 70% of its maximum strength upon shifting to the displacement of 5.0 Å. Stacking interactions of RAHB rings can, in some cases, preserve similar portion of their strength (around 70%) at large displacements.",
journal = "VIII International Congress “Engineering, Environment and Materials in Process Industry“",
title = "Resonance-Assisted Hydrogen-Bridged Rings: Parallel Alignment in Crystal Structures and Significant Noncovalent Attraction",
url = "https://hdl.handle.net/21.15107/rcub_cherry_6404"
}

Blagojević Filipović, J. P.,& Zarić, S. D.. (2023). Resonance-Assisted Hydrogen-Bridged Rings: Parallel Alignment in Crystal Structures and Significant Noncovalent Attraction. in VIII International Congress “Engineering, Environment and Materials in Process Industry“.
https://hdl.handle.net/21.15107/rcub_cherry_6404

Blagojević Filipović JP, Zarić SD. Resonance-Assisted Hydrogen-Bridged Rings: Parallel Alignment in Crystal Structures and Significant Noncovalent Attraction. in VIII International Congress “Engineering, Environment and Materials in Process Industry“. 2023;.
https://hdl.handle.net/21.15107/rcub_cherry_6404 .

Blagojević Filipović, Jelena P., Zarić, Snežana D., "Resonance-Assisted Hydrogen-Bridged Rings: Parallel Alignment in Crystal Structures and Significant Noncovalent Attraction" in VIII International Congress “Engineering, Environment and Materials in Process Industry“ (2023),
https://hdl.handle.net/21.15107/rcub_cherry_6404 .

TY  - CONF
AU  - Blagojević Filipović, Jelena P.
AU  - Zarić, Snežana D.
PY  - 2022
UR  - http://cherry.chem.bg.ac.rs/handle/123456789/6443
AB  - Some systems that form stacking interactions conserve large portion of their strength upon shifting to large horizontal displacements, which might have implications on molecular recognition.[1] The possibility of RAHB/RAHB and RAHB/C6-aromatic systems to form stacking at large horizontal displacements is studied in this work. Large part of parallel RAHB/RAHB and RAHB/C6-aromatic contacts found in the Cambridge Structural Database (CSD) are classified as large offset stacking (44% and 47%, respectively).[2] Crystal structures of both RAHB/RAHB and RAHB/C6-aromatic systems are organized into parallel layers, unlike benzene crystal structures. Quantum chemical calculations show that the contacts at large offsets found in the CSD are not just the consequence of crystal packing. The calculated potential energy curves reveal the existence of certain stabilizations at large offsets (plateaus and even shallow minima). The large offset stacking interaction energies can be significant even at interplane separations typical for stacking (3.0-4.0 Å), or slightly smaller (Figure 1). In some systems, up to 66% of the strongest calculated interaction energy can be preserved upon shifting to large offsets.[2]
PB  - University of Strasbourg
C3  - 2nd International Conferences on Noncovalent Interactions (ICNI2022), 18-22 July, 2022, Strasbourg, France
T1  - Stacking Interactions of Resonance-Assisted Hydrogen-Bridged (RAHB) Rings; Significant Attraction at Large Displacements
UR  - https://hdl.handle.net/21.15107/rcub_cherry_6443
ER  - 

@conference{
author = "Blagojević Filipović, Jelena P. and Zarić, Snežana D.",
year = "2022",
abstract = "Some systems that form stacking interactions conserve large portion of their strength upon shifting to large horizontal displacements, which might have implications on molecular recognition.[1] The possibility of RAHB/RAHB and RAHB/C6-aromatic systems to form stacking at large horizontal displacements is studied in this work. Large part of parallel RAHB/RAHB and RAHB/C6-aromatic contacts found in the Cambridge Structural Database (CSD) are classified as large offset stacking (44% and 47%, respectively).[2] Crystal structures of both RAHB/RAHB and RAHB/C6-aromatic systems are organized into parallel layers, unlike benzene crystal structures. Quantum chemical calculations show that the contacts at large offsets found in the CSD are not just the consequence of crystal packing. The calculated potential energy curves reveal the existence of certain stabilizations at large offsets (plateaus and even shallow minima). The large offset stacking interaction energies can be significant even at interplane separations typical for stacking (3.0-4.0 Å), or slightly smaller (Figure 1). In some systems, up to 66% of the strongest calculated interaction energy can be preserved upon shifting to large offsets.[2]",
publisher = "University of Strasbourg",
journal = "2nd International Conferences on Noncovalent Interactions (ICNI2022), 18-22 July, 2022, Strasbourg, France",
title = "Stacking Interactions of Resonance-Assisted Hydrogen-Bridged (RAHB) Rings; Significant Attraction at Large Displacements",
url = "https://hdl.handle.net/21.15107/rcub_cherry_6443"
}

Blagojević Filipović, J. P.,& Zarić, S. D.. (2022). Stacking Interactions of Resonance-Assisted Hydrogen-Bridged (RAHB) Rings; Significant Attraction at Large Displacements. in 2nd International Conferences on Noncovalent Interactions (ICNI2022), 18-22 July, 2022, Strasbourg, France
University of Strasbourg..
https://hdl.handle.net/21.15107/rcub_cherry_6443

Blagojević Filipović JP, Zarić SD. Stacking Interactions of Resonance-Assisted Hydrogen-Bridged (RAHB) Rings; Significant Attraction at Large Displacements. in 2nd International Conferences on Noncovalent Interactions (ICNI2022), 18-22 July, 2022, Strasbourg, France. 2022;.
https://hdl.handle.net/21.15107/rcub_cherry_6443 .

Blagojević Filipović, Jelena P., Zarić, Snežana D., "Stacking Interactions of Resonance-Assisted Hydrogen-Bridged (RAHB) Rings; Significant Attraction at Large Displacements" in 2nd International Conferences on Noncovalent Interactions (ICNI2022), 18-22 July, 2022, Strasbourg, France (2022),
https://hdl.handle.net/21.15107/rcub_cherry_6443 .

TY  - CONF
AU  - Malenov, Dušan P.
AU  - Blagojević Filipović, Jelena P.
AU  - Zarić, Snežana D.
PY  - 2022
UR  - http://cherry.chem.bg.ac.rs/handle/123456789/6349
AB  - Crystal structures of the methylated cyclopentadienyl (Cp) complexes are systematically analysed by searching the Cambridge Structural Database (CSD) and the preferred positions of the stacked methylated Cp ligands are described. The stacking contacts of the Me5Cp complexes are by far the most frequently found in the CSD (3632 contacts), followed by MeCp (446) and Me4Cp (151). These contacts mostly correspond to simultaneous parallel-displaced stacking and CH/π interactions, as well as paralleldisplaced stacking and stacking interactions at large horizontal displacements. With increasing the number of methyl substituents the occurrence of stacking with large displacements decreases (48.4% for MeCp, 28.5% for Me4Cp, 3.8% for Me5Cp), because CH/π interactions stabilize geometries with smaller displacements. Different interaction types can be explained by the electrostatic potential maps of the studied complexes.
AB  - Кристалне структуре метилованих (Me) циклопентадиенилних (Cp) комплекса су систематски анализиране претрагом Кембричке базе структурних података (CSD) и описани су преовлађујући положаји метилованих Cp лиганада у стекинг оријентацији. Стекинг контакти Me5Cp комплекса су далеко најучесталији (3632 контакта), a затим следе MeCp (446) и Me4Cp (151). Kонтакти у највећој мери садрже симултане паралелно-померене стекинг интеракције и CH/π интеракције, али се јављају и саме паралелно-померене стекинг интеракције и стекинг интеракције са великим хоризонталним померањима. Са повећањем броја метил-супституената опада заступљеност стекинга на великим померањима (48,4% за MeCp, 28,5% за Me4Cp, 3,8% за Me5Cp), пошто CH/π интеракције стабилизују геометрије на мањим померањима. Различити типови интеракција се могу објаснити на основу мапа електростатичких потенцијала испитиваних комплекса.
C3  - 58th Meeting of the Serbian Chemical Society, Belgrade, Serbia, 9th-10th June, 2022. In: Book of Abstracts and Proceedings
T1  - Stacking of the methylated cyclopentadienyl ligands in crystal structures of transition metal complexes
T1  - Стекинг метилованих циклопентадиенилних лиганада у кристалним структурама комплекса прелазних метала
UR  - https://hdl.handle.net/21.15107/rcub_cherry_6349
ER  - 

@conference{
author = "Malenov, Dušan P. and Blagojević Filipović, Jelena P. and Zarić, Snežana D.",
year = "2022",
abstract = "Crystal structures of the methylated cyclopentadienyl (Cp) complexes are systematically analysed by searching the Cambridge Structural Database (CSD) and the preferred positions of the stacked methylated Cp ligands are described. The stacking contacts of the Me5Cp complexes are by far the most frequently found in the CSD (3632 contacts), followed by MeCp (446) and Me4Cp (151). These contacts mostly correspond to simultaneous parallel-displaced stacking and CH/π interactions, as well as paralleldisplaced stacking and stacking interactions at large horizontal displacements. With increasing the number of methyl substituents the occurrence of stacking with large displacements decreases (48.4% for MeCp, 28.5% for Me4Cp, 3.8% for Me5Cp), because CH/π interactions stabilize geometries with smaller displacements. Different interaction types can be explained by the electrostatic potential maps of the studied complexes., Кристалне структуре метилованих (Me) циклопентадиенилних (Cp) комплекса су систематски анализиране претрагом Кембричке базе структурних података (CSD) и описани су преовлађујући положаји метилованих Cp лиганада у стекинг оријентацији. Стекинг контакти Me5Cp комплекса су далеко најучесталији (3632 контакта), a затим следе MeCp (446) и Me4Cp (151). Kонтакти у највећој мери садрже симултане паралелно-померене стекинг интеракције и CH/π интеракције, али се јављају и саме паралелно-померене стекинг интеракције и стекинг интеракције са великим хоризонталним померањима. Са повећањем броја метил-супституената опада заступљеност стекинга на великим померањима (48,4% за MeCp, 28,5% за Me4Cp, 3,8% за Me5Cp), пошто CH/π интеракције стабилизују геометрије на мањим померањима. Различити типови интеракција се могу објаснити на основу мапа електростатичких потенцијала испитиваних комплекса.",
journal = "58th Meeting of the Serbian Chemical Society, Belgrade, Serbia, 9th-10th June, 2022. In: Book of Abstracts and Proceedings",
title = "Stacking of the methylated cyclopentadienyl ligands in crystal structures of transition metal complexes, Стекинг метилованих циклопентадиенилних лиганада у кристалним структурама комплекса прелазних метала",
url = "https://hdl.handle.net/21.15107/rcub_cherry_6349"
}

Malenov, D. P., Blagojević Filipović, J. P.,& Zarić, S. D.. (2022). Stacking of the methylated cyclopentadienyl ligands in crystal structures of transition metal complexes. in 58th Meeting of the Serbian Chemical Society, Belgrade, Serbia, 9th-10th June, 2022. In: Book of Abstracts and Proceedings.
https://hdl.handle.net/21.15107/rcub_cherry_6349

Malenov DP, Blagojević Filipović JP, Zarić SD. Stacking of the methylated cyclopentadienyl ligands in crystal structures of transition metal complexes. in 58th Meeting of the Serbian Chemical Society, Belgrade, Serbia, 9th-10th June, 2022. In: Book of Abstracts and Proceedings. 2022;.
https://hdl.handle.net/21.15107/rcub_cherry_6349 .

Malenov, Dušan P., Blagojević Filipović, Jelena P., Zarić, Snežana D., "Stacking of the methylated cyclopentadienyl ligands in crystal structures of transition metal complexes" in 58th Meeting of the Serbian Chemical Society, Belgrade, Serbia, 9th-10th June, 2022. In: Book of Abstracts and Proceedings (2022),
https://hdl.handle.net/21.15107/rcub_cherry_6349 .

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  - Blagojević Filipović, Jelena P.
AU  - Zarić, Snežana D.
PY  - 2021
UR  - http://cherry.chem.bg.ac.rs/handle/123456789/4790
AB  - The stacking contacts between two resonance-assisted hydrogen-bridged (RAHB) rings and stacking contacts between RAHB rings and C6-aromatic groups are frequently found at large horizontal displacements in the crystal structures found in the Cambridge Structural Database (CSD), particularly in the range of 4.0–6.0 and 5.5–6.5 Å, respectively. Ab initio calculations reveal that interactions at large offsets, although weaker than interactions at smaller offsets, can be significant, since a large portion of interaction energy (in some systems up to 66%) can be preserved upon shifting to larger offset values.
PB  - American Chemical Society
T2  - Crystal Growth & Design
T1  - Significant Stacking Interactions of Resonance-Assisted Hydrogen-Bridged (RAHB) Rings at Large Horizontal Displacements
VL  - 21
IS  - 9
SP  - 4947
EP  - 4958
DO  - 10.1021/acs.cgd.1c00392
ER  - 

@article{
author = "Blagojević Filipović, Jelena P. and Zarić, Snežana D.",
year = "2021",
abstract = "The stacking contacts between two resonance-assisted hydrogen-bridged (RAHB) rings and stacking contacts between RAHB rings and C6-aromatic groups are frequently found at large horizontal displacements in the crystal structures found in the Cambridge Structural Database (CSD), particularly in the range of 4.0–6.0 and 5.5–6.5 Å, respectively. Ab initio calculations reveal that interactions at large offsets, although weaker than interactions at smaller offsets, can be significant, since a large portion of interaction energy (in some systems up to 66%) can be preserved upon shifting to larger offset values.",
publisher = "American Chemical Society",
journal = "Crystal Growth & Design",
title = "Significant Stacking Interactions of Resonance-Assisted Hydrogen-Bridged (RAHB) Rings at Large Horizontal Displacements",
volume = "21",
number = "9",
pages = "4947-4958",
doi = "10.1021/acs.cgd.1c00392"
}

Blagojević Filipović, J. P.,& Zarić, S. D.. (2021). Significant Stacking Interactions of Resonance-Assisted Hydrogen-Bridged (RAHB) Rings at Large Horizontal Displacements. in Crystal Growth & Design
American Chemical Society., 21(9), 4947-4958.
https://doi.org/10.1021/acs.cgd.1c00392

Blagojević Filipović JP, Zarić SD. Significant Stacking Interactions of Resonance-Assisted Hydrogen-Bridged (RAHB) Rings at Large Horizontal Displacements. in Crystal Growth & Design. 2021;21(9):4947-4958.
doi:10.1021/acs.cgd.1c00392 .

Blagojević Filipović, Jelena P., Zarić, Snežana D., "Significant Stacking Interactions of Resonance-Assisted Hydrogen-Bridged (RAHB) Rings at Large Horizontal Displacements" in Crystal Growth & Design, 21, no. 9 (2021):4947-4958,
https://doi.org/10.1021/acs.cgd.1c00392 . .

TY  - CONF
AU  - Blagojević Filipović, Jelena P.
AU  - Zarić, Snežana D.
PY  - 2021
UR  - http://cherry.chem.bg.ac.rs/handle/123456789/5264
AB  - The Cambridge Structural Database (CSD) is searched for mutual contacts between six-membered resonance-assisted hydrogenbridged
rings (RAHB) (the example of a fragment is shown in Fig. 1a) [1] and for contacts between six-membered RAHB rings and
C6-aromatic rings (Fig. 1b). There is a quite large prevalence of parallel contacts in the set of RAHB/RAHB contacts, since 91% from
totally 678 contacts found are parallel contacts, mostly with antiparallel orientation of the rings [1]. At the other side, the prevalence of
parallel contacts in the set of RAHB/C6-aromatic contacts is not so pronounced, since 59% from totally 677 contacts found are parallel
contacts. The distances between the interacting ring planes are mostly between 3.0 and 4.0 Å, while horizontal displacements are
mostly in the range 0.0-3.0 Å in both parallel RAHB/RAHB and RAHB/C6-aromatic contacts.
The interaction energy calculations were performed on stacked dimer model systems based on abundance in the CSD. The strongest
calculated RAHB/RAHB interaction is -4.7 kcal/mol, while the strongest calculated RAHB/benzene interaction is significantly weaker
-3.7 kcal/mol. However, RAHB/RAHB stacking interactions can be stronger or weaker than the corresponding RAHB/benzene
stacking interactions, depending on the RAHB ring system. The Symmetry Adopted Perturbation Theory (SAPT) calculations show
that the dominant contribution in total RAHB/RAHB stacking interaction energy is the dispersion term, which can be mostly or
completely cancelled by the exchange repulsion term, hence, the electrostatic term can be effectively dominant. Depending on the
RAHB ring system, the electrostatic contribution can be practically equal to the net dispersion contribution (the sum of dispersion and
exchange-repulsion terms) [1]. The electrostatic term is effectively dominant in all RAHB/benzene systems observed, due to the
almost complete cancellation of the dispersion by the exchange-repulsion terms.
C3  - 25th Congress of the International Union of Crystallography
T1  - Supramolecular arrangements in the crystal structures and the interaction energy calculations of resonance-assisted hydrogen-bridged (RAHB) rings - RAHB/RAHB and RAHB/C6-aromatic contacts
UR  - https://hdl.handle.net/21.15107/rcub_cherry_5264
ER  - 

@conference{
author = "Blagojević Filipović, Jelena P. and Zarić, Snežana D.",
year = "2021",
abstract = "The Cambridge Structural Database (CSD) is searched for mutual contacts between six-membered resonance-assisted hydrogenbridged
rings (RAHB) (the example of a fragment is shown in Fig. 1a) [1] and for contacts between six-membered RAHB rings and
C6-aromatic rings (Fig. 1b). There is a quite large prevalence of parallel contacts in the set of RAHB/RAHB contacts, since 91% from
totally 678 contacts found are parallel contacts, mostly with antiparallel orientation of the rings [1]. At the other side, the prevalence of
parallel contacts in the set of RAHB/C6-aromatic contacts is not so pronounced, since 59% from totally 677 contacts found are parallel
contacts. The distances between the interacting ring planes are mostly between 3.0 and 4.0 Å, while horizontal displacements are
mostly in the range 0.0-3.0 Å in both parallel RAHB/RAHB and RAHB/C6-aromatic contacts.
The interaction energy calculations were performed on stacked dimer model systems based on abundance in the CSD. The strongest
calculated RAHB/RAHB interaction is -4.7 kcal/mol, while the strongest calculated RAHB/benzene interaction is significantly weaker
-3.7 kcal/mol. However, RAHB/RAHB stacking interactions can be stronger or weaker than the corresponding RAHB/benzene
stacking interactions, depending on the RAHB ring system. The Symmetry Adopted Perturbation Theory (SAPT) calculations show
that the dominant contribution in total RAHB/RAHB stacking interaction energy is the dispersion term, which can be mostly or
completely cancelled by the exchange repulsion term, hence, the electrostatic term can be effectively dominant. Depending on the
RAHB ring system, the electrostatic contribution can be practically equal to the net dispersion contribution (the sum of dispersion and
exchange-repulsion terms) [1]. The electrostatic term is effectively dominant in all RAHB/benzene systems observed, due to the
almost complete cancellation of the dispersion by the exchange-repulsion terms.",
journal = "25th Congress of the International Union of Crystallography",
title = "Supramolecular arrangements in the crystal structures and the interaction energy calculations of resonance-assisted hydrogen-bridged (RAHB) rings - RAHB/RAHB and RAHB/C6-aromatic contacts",
url = "https://hdl.handle.net/21.15107/rcub_cherry_5264"
}

Blagojević Filipović, J. P.,& Zarić, S. D.. (2021). Supramolecular arrangements in the crystal structures and the interaction energy calculations of resonance-assisted hydrogen-bridged (RAHB) rings - RAHB/RAHB and RAHB/C6-aromatic contacts. in 25th Congress of the International Union of Crystallography.
https://hdl.handle.net/21.15107/rcub_cherry_5264

Blagojević Filipović JP, Zarić SD. Supramolecular arrangements in the crystal structures and the interaction energy calculations of resonance-assisted hydrogen-bridged (RAHB) rings - RAHB/RAHB and RAHB/C6-aromatic contacts. in 25th Congress of the International Union of Crystallography. 2021;.
https://hdl.handle.net/21.15107/rcub_cherry_5264 .

Blagojević Filipović, Jelena P., Zarić, Snežana D., "Supramolecular arrangements in the crystal structures and the interaction energy calculations of resonance-assisted hydrogen-bridged (RAHB) rings - RAHB/RAHB and RAHB/C6-aromatic contacts" in 25th Congress of the International Union of Crystallography (2021),
https://hdl.handle.net/21.15107/rcub_cherry_5264 .

TY  - CONF
AU  - Blagojević Filipović, Jelena P.
AU  - Zarić, Snežana D.
PY  - 2021
UR  - http://cherry.chem.bg.ac.rs/handle/123456789/5270
AB  - The Symmetry Adapted Perturbation Theory (SAPT) energy decomposition
analysis is applied for studying the nature of stacking interaction occurring
in homodimers of resonance-assisted hydrogen-bridged (RAHB) rings and
heterodimers of RAHB and benzene rings. The contribution of various
energy terms is dependent on the composition of a RAHB ring and can be
rationalized based on electrostatic potential maps.
C3  - 15th International Conference on Fundamental and Applied Aspects of Physical Chemistry
T1  - The nature of stacking interactions of the resonance-assisted hydrogen-bridged rings
UR  - https://hdl.handle.net/21.15107/rcub_cherry_5270
ER  - 

@conference{
author = "Blagojević Filipović, Jelena P. and Zarić, Snežana D.",
year = "2021",
abstract = "The Symmetry Adapted Perturbation Theory (SAPT) energy decomposition
analysis is applied for studying the nature of stacking interaction occurring
in homodimers of resonance-assisted hydrogen-bridged (RAHB) rings and
heterodimers of RAHB and benzene rings. The contribution of various
energy terms is dependent on the composition of a RAHB ring and can be
rationalized based on electrostatic potential maps.",
journal = "15th International Conference on Fundamental and Applied Aspects of Physical Chemistry",
title = "The nature of stacking interactions of the resonance-assisted hydrogen-bridged rings",
url = "https://hdl.handle.net/21.15107/rcub_cherry_5270"
}

Blagojević Filipović, J. P.,& Zarić, S. D.. (2021). The nature of stacking interactions of the resonance-assisted hydrogen-bridged rings. in 15th International Conference on Fundamental and Applied Aspects of Physical Chemistry.
https://hdl.handle.net/21.15107/rcub_cherry_5270

Blagojević Filipović JP, Zarić SD. The nature of stacking interactions of the resonance-assisted hydrogen-bridged rings. in 15th International Conference on Fundamental and Applied Aspects of Physical Chemistry. 2021;.
https://hdl.handle.net/21.15107/rcub_cherry_5270 .

Blagojević Filipović, Jelena P., Zarić, Snežana D., "The nature of stacking interactions of the resonance-assisted hydrogen-bridged rings" in 15th International Conference on Fundamental and Applied Aspects of Physical Chemistry (2021),
https://hdl.handle.net/21.15107/rcub_cherry_5270 .

TY  - JOUR
AU  - Malenov, Dušan P.
AU  - Blagojević Filipović, Jelena P.
AU  - Zarić, Snežana D.
PY  - 2020
UR  - https://cherry.chem.bg.ac.rs/handle/123456789/4029
AB  - In the crystal structures of methylated cyclopentadienyl (Cp) complexes (MeCp, Me4Cp and Me5Cp) deposited in the Cambridge Structural Database, certain orientation types of stacked contacts can be noted as the most frequent. These orientation preferences can be well explained by the matching of oppositely charged regions of electrostatic potential. Parallel displaced stacking, large offset stacking and C - H⋯π interactions are the dominant interaction types that are responsible for the arrangement in the crystal structures of stacked methylated Cp complexes.
PB  - International Union of Crystallography
T2  - Acta Crystallographica Section B: Structural Science, Crystal Engineering and Materials
T1  - Stacking interactions of the methyl­ated cyclo­pentadienyl ligands in the crystal structures of transition metal complexes
VL  - 76
IS  - 2
SP  - 252
EP  - 258
DO  - 10.1107/S2052520620002206
ER  - 

@article{
author = "Malenov, Dušan P. and Blagojević Filipović, Jelena P. and Zarić, Snežana D.",
year = "2020",
abstract = "In the crystal structures of methylated cyclopentadienyl (Cp) complexes (MeCp, Me4Cp and Me5Cp) deposited in the Cambridge Structural Database, certain orientation types of stacked contacts can be noted as the most frequent. These orientation preferences can be well explained by the matching of oppositely charged regions of electrostatic potential. Parallel displaced stacking, large offset stacking and C - H⋯π interactions are the dominant interaction types that are responsible for the arrangement in the crystal structures of stacked methylated Cp complexes.",
publisher = "International Union of Crystallography",
journal = "Acta Crystallographica Section B: Structural Science, Crystal Engineering and Materials",
title = "Stacking interactions of the methyl­ated cyclo­pentadienyl ligands in the crystal structures of transition metal complexes",
volume = "76",
number = "2",
pages = "252-258",
doi = "10.1107/S2052520620002206"
}

Malenov, D. P., Blagojević Filipović, J. P.,& Zarić, S. D.. (2020). Stacking interactions of the methyl­ated cyclo­pentadienyl ligands in the crystal structures of transition metal complexes. in Acta Crystallographica Section B: Structural Science, Crystal Engineering and Materials
International Union of Crystallography., 76(2), 252-258.
https://doi.org/10.1107/S2052520620002206

Malenov DP, Blagojević Filipović JP, Zarić SD. Stacking interactions of the methyl­ated cyclo­pentadienyl ligands in the crystal structures of transition metal complexes. in Acta Crystallographica Section B: Structural Science, Crystal Engineering and Materials. 2020;76(2):252-258.
doi:10.1107/S2052520620002206 .

Malenov, Dušan P., Blagojević Filipović, Jelena P., Zarić, Snežana D., "Stacking interactions of the methyl­ated cyclo­pentadienyl ligands in the crystal structures of transition metal complexes" in Acta Crystallographica Section B: Structural Science, Crystal Engineering and Materials, 76, no. 2 (2020):252-258,
https://doi.org/10.1107/S2052520620002206 . .

TY  - JOUR
AU  - Blagojević Filipović, Jelena P.
AU  - Hall, Michael B.
AU  - Zarić, Snežana D.
PY  - 2020
UR  - http://cherry.chem.bg.ac.rs/handle/123456789/5307
AB  - Stacking interactions between six-membered resonance-assisted hydrogen-bridged rings (RAHB) and C6-aromatic rings are systematically studied by analyzing crystal structures in Cambridge Structural Database (CSD). The interaction energies were calculated by quantum-chemical methods. Although the interactions are stronger than benzene/benzene stacking interactions (-2.7 kcal/mol) the strongest calculated RAHB/benzene stacking interaction (-3.7 kcal/mol) is significantly weaker than the strongest calculated RAHB/RAHB stacking interaction (-4.7 kcal/mol), but for particular composition of RAHB rings RAHB/benzene stacking interactions can be weaker or stronger than the corresponding RAHB/RAHB stacking interactions. They are also weaker than the strongest calculated stacking interaction between five-membered saturated hydrogen-bridged rings and benzene (-4.4 kcal/mol) and between two five-membered saturated hydrogen-bridged rings (-4.9 kcal/mol). SAPT energy decomposition analyses show that the strongest attractive term in RAHB/benzene stacking interactions is dispersion, however, it is mostly canceled by repulsive exchange term, hence the geometries of the most stable structures are determined by electrostatic term.
PB  - Royal Society of Chemistry
T2  - Physical Chemistry Chemical Physics
T1  - Stacking Interactions of Resonance-Assisted Hydrogen-Bridged Rings and C6-Aromatic Rings
VL  - 22
IS  - 24
SP  - 13721
EP  - 13728
DO  - 10.1039/D0CP01624A
ER  - 

@article{
author = "Blagojević Filipović, Jelena P. and Hall, Michael B. and Zarić, Snežana D.",
year = "2020",
abstract = "Stacking interactions between six-membered resonance-assisted hydrogen-bridged rings (RAHB) and C6-aromatic rings are systematically studied by analyzing crystal structures in Cambridge Structural Database (CSD). The interaction energies were calculated by quantum-chemical methods. Although the interactions are stronger than benzene/benzene stacking interactions (-2.7 kcal/mol) the strongest calculated RAHB/benzene stacking interaction (-3.7 kcal/mol) is significantly weaker than the strongest calculated RAHB/RAHB stacking interaction (-4.7 kcal/mol), but for particular composition of RAHB rings RAHB/benzene stacking interactions can be weaker or stronger than the corresponding RAHB/RAHB stacking interactions. They are also weaker than the strongest calculated stacking interaction between five-membered saturated hydrogen-bridged rings and benzene (-4.4 kcal/mol) and between two five-membered saturated hydrogen-bridged rings (-4.9 kcal/mol). SAPT energy decomposition analyses show that the strongest attractive term in RAHB/benzene stacking interactions is dispersion, however, it is mostly canceled by repulsive exchange term, hence the geometries of the most stable structures are determined by electrostatic term.",
publisher = "Royal Society of Chemistry",
journal = "Physical Chemistry Chemical Physics",
title = "Stacking Interactions of Resonance-Assisted Hydrogen-Bridged Rings and C6-Aromatic Rings",
volume = "22",
number = "24",
pages = "13721-13728",
doi = "10.1039/D0CP01624A"
}

Blagojević Filipović, J. P., Hall, M. B.,& Zarić, S. D.. (2020). Stacking Interactions of Resonance-Assisted Hydrogen-Bridged Rings and C6-Aromatic Rings. in Physical Chemistry Chemical Physics
Royal Society of Chemistry., 22(24), 13721-13728.
https://doi.org/10.1039/D0CP01624A

Blagojević Filipović JP, Hall MB, Zarić SD. Stacking Interactions of Resonance-Assisted Hydrogen-Bridged Rings and C6-Aromatic Rings. in Physical Chemistry Chemical Physics. 2020;22(24):13721-13728.
doi:10.1039/D0CP01624A .

Blagojević Filipović, Jelena P., Hall, Michael B., Zarić, Snežana D., "Stacking Interactions of Resonance-Assisted Hydrogen-Bridged Rings and C6-Aromatic Rings" in Physical Chemistry Chemical Physics, 22, no. 24 (2020):13721-13728,
https://doi.org/10.1039/D0CP01624A . .

TY  - CONF
AU  - Blagojević Filipović, Jelena P.
AU  - Zarić, Snežana D.
PY  - 2020
UR  - http://cherry.chem.bg.ac.rs/handle/123456789/5308
AB  - Supramolecular arrangements of RAHB/RAHB and RAHB/C6-aromatic contacts were studied by the Cambridge Structural Database (CSD) search, while interaction energies of these interactions were calculated on dimer model systems by using quantum-chemical methods. Parallel alignment contacts are quite dominant in the crystal structures of these species, since 91% of the RAHB/RAHB contacts, satisfying the search criteria [1], are parallel, while that preference is not so large in RAHB/C6-aromatic contacts, since 59% of them are parallel [2]. Interplane separations of the parallel contacts of both systems are between 3.0 and 4.0 Å, which is a characteristic of stacking interactions. Examples of the RAHB/RAHB and RAHB/C6-aromatic contacts are given in Figure 1.
Model systems for quantum chemical calculations are based on abundance in the crystal structures. Energy decomposition analysis is also performed by using Symmetry Adopted Perturbation Theory (SAPT) calculations. The strongest calculated RAHB/RAHB interaction is -4.7 kcal/mol. Electrostatic contribution is dominant or equal to the net dispersion (the sum of dispersion and exchange-repulsion terms). The strongest calculated RAHB/benzene interaction is -3.7 kcal/mol, but RAHB/benzene interactions can be stronger or weaker than the corresponding RAHB/RAHB interactions.
C3  - 4th International Symposium on Halogen Bonding, ISXB4
T1  - Stacking interactions of resonance-assisted hydrogen-bridged (RAHB) rings - RAHB/RAHB and RAHB/C6-aromatic systems
UR  - https://hdl.handle.net/21.15107/rcub_cherry_5308
ER  - 

@conference{
author = "Blagojević Filipović, Jelena P. and Zarić, Snežana D.",
year = "2020",
abstract = "Supramolecular arrangements of RAHB/RAHB and RAHB/C6-aromatic contacts were studied by the Cambridge Structural Database (CSD) search, while interaction energies of these interactions were calculated on dimer model systems by using quantum-chemical methods. Parallel alignment contacts are quite dominant in the crystal structures of these species, since 91% of the RAHB/RAHB contacts, satisfying the search criteria [1], are parallel, while that preference is not so large in RAHB/C6-aromatic contacts, since 59% of them are parallel [2]. Interplane separations of the parallel contacts of both systems are between 3.0 and 4.0 Å, which is a characteristic of stacking interactions. Examples of the RAHB/RAHB and RAHB/C6-aromatic contacts are given in Figure 1.
Model systems for quantum chemical calculations are based on abundance in the crystal structures. Energy decomposition analysis is also performed by using Symmetry Adopted Perturbation Theory (SAPT) calculations. The strongest calculated RAHB/RAHB interaction is -4.7 kcal/mol. Electrostatic contribution is dominant or equal to the net dispersion (the sum of dispersion and exchange-repulsion terms). The strongest calculated RAHB/benzene interaction is -3.7 kcal/mol, but RAHB/benzene interactions can be stronger or weaker than the corresponding RAHB/RAHB interactions.",
journal = "4th International Symposium on Halogen Bonding, ISXB4",
title = "Stacking interactions of resonance-assisted hydrogen-bridged (RAHB) rings - RAHB/RAHB and RAHB/C6-aromatic systems",
url = "https://hdl.handle.net/21.15107/rcub_cherry_5308"
}

Blagojević Filipović, J. P.,& Zarić, S. D.. (2020). Stacking interactions of resonance-assisted hydrogen-bridged (RAHB) rings - RAHB/RAHB and RAHB/C6-aromatic systems. in 4th International Symposium on Halogen Bonding, ISXB4.
https://hdl.handle.net/21.15107/rcub_cherry_5308

Blagojević Filipović JP, Zarić SD. Stacking interactions of resonance-assisted hydrogen-bridged (RAHB) rings - RAHB/RAHB and RAHB/C6-aromatic systems. in 4th International Symposium on Halogen Bonding, ISXB4. 2020;.
https://hdl.handle.net/21.15107/rcub_cherry_5308 .

Blagojević Filipović, Jelena P., Zarić, Snežana D., "Stacking interactions of resonance-assisted hydrogen-bridged (RAHB) rings - RAHB/RAHB and RAHB/C6-aromatic systems" in 4th International Symposium on Halogen Bonding, ISXB4 (2020),
https://hdl.handle.net/21.15107/rcub_cherry_5308 .

TY  - JOUR
AU  - Ninković, Dragan
AU  - Blagojević Filipović, Jelena P.
AU  - Hall, Michael B.
AU  - Brothers, Edward N.
AU  - Zarić, Snežana D.
PY  - 2020
UR  - https://cherry.chem.bg.ac.rs/handle/123456789/3946
AB  - High-level ab initio calculations show that the most stable stacking for benzene-cyclohexane is 17% stronger than that for benzene-benzene. However, as these systems are displaced horizontally the benzene-benzene attraction retains its strength. At a displacement of 5.0 Å, the benzene-benzene attraction is still ∼70% of its maximum strength, while benzene-cyclohexane attraction has fallen to ∼40% of its maximum strength. Alternatively, the radius of attraction (>2.0 kcal/mol) for benzene-benzene is 250% larger than that for benzene-cyclohexane. Thus, at relatively large distances aromatic rings can recognize each other, a phenomenon that helps explain their importance in protein folding and supramolecular structures.
PB  - American Chemical Society
T2  - ACS Central Science
T1  - What Is Special about Aromatic-Aromatic Interactions? Significant Attraction at Large Horizontal Displacement
VL  - 6
IS  - 3
SP  - 420
EP  - 425
DO  - 10.1021/acscentsci.0c00005
ER  - 

@article{
author = "Ninković, Dragan and Blagojević Filipović, Jelena P. and Hall, Michael B. and Brothers, Edward N. and Zarić, Snežana D.",
year = "2020",
abstract = "High-level ab initio calculations show that the most stable stacking for benzene-cyclohexane is 17% stronger than that for benzene-benzene. However, as these systems are displaced horizontally the benzene-benzene attraction retains its strength. At a displacement of 5.0 Å, the benzene-benzene attraction is still ∼70% of its maximum strength, while benzene-cyclohexane attraction has fallen to ∼40% of its maximum strength. Alternatively, the radius of attraction (>2.0 kcal/mol) for benzene-benzene is 250% larger than that for benzene-cyclohexane. Thus, at relatively large distances aromatic rings can recognize each other, a phenomenon that helps explain their importance in protein folding and supramolecular structures.",
publisher = "American Chemical Society",
journal = "ACS Central Science",
title = "What Is Special about Aromatic-Aromatic Interactions? Significant Attraction at Large Horizontal Displacement",
volume = "6",
number = "3",
pages = "420-425",
doi = "10.1021/acscentsci.0c00005"
}

Ninković, D., Blagojević Filipović, J. P., Hall, M. B., Brothers, E. N.,& Zarić, S. D.. (2020). What Is Special about Aromatic-Aromatic Interactions? Significant Attraction at Large Horizontal Displacement. in ACS Central Science
American Chemical Society., 6(3), 420-425.
https://doi.org/10.1021/acscentsci.0c00005

Ninković D, Blagojević Filipović JP, Hall MB, Brothers EN, Zarić SD. What Is Special about Aromatic-Aromatic Interactions? Significant Attraction at Large Horizontal Displacement. in ACS Central Science. 2020;6(3):420-425.
doi:10.1021/acscentsci.0c00005 .

Ninković, Dragan, Blagojević Filipović, Jelena P., Hall, Michael B., Brothers, Edward N., Zarić, Snežana D., "What Is Special about Aromatic-Aromatic Interactions? Significant Attraction at Large Horizontal Displacement" in ACS Central Science, 6, no. 3 (2020):420-425,
https://doi.org/10.1021/acscentsci.0c00005 . .

TY  - JOUR
AU  - Stanković, Ivana M.
AU  - Blagojević Filipović, Jelena P.
AU  - Zarić, Snežana D.
PY  - 2020
UR  - https://cherry.chem.bg.ac.rs/handle/123456789/3983
AB  - The geometries of the contacts between monosaccharides and aromatic rings of amino acids found in X-ray crystallography structures, in the Protein Data Bank (PDB), were analyzed, while the energies of the interactions were calculated using quantum chemical method. We found 1913 sugar/aromatic ring contacts, 1054 of them (55%) with CH/π interactions and 859 of them (45%) without CH/π interactions. We showed that only the carbohydrate/aromatic contacts with CH/π interactions are preferentially parallel and enable sliding in the plane parallel to aromatic ring. The calculated interaction energies in systems with CH/π interactions are in the range from −1.7 kcal/mol to −6.8 kcal/mol, while in the systems without CH/π interactions are in the range −0.2 to −3.2 kcal/mol. Hence, the binding that does not include CH/π interactions, can also be important for aromatic amino acid and carbohydrate binding processes, since some of these interactions can be as strong as the CH/π interactions. At the same time, these interactions can be weak enough to enable releasing of small carbohydrate fragments after the enzymatic reaction. The analysis of the protein-substrate patterns showed that every second or third carbohydrate unit in long substrates stacks with protein aromatic amino acids.
PB  - Elsevier
T2  - International Journal of Biological Macromolecules
T1  - Carbohydrate – Protein aromatic ring interactions beyond CH/π interactions: A Protein Data Bank survey and quantum chemical calculations
VL  - 157
SP  - 1
EP  - 9
DO  - 10.1016/j.ijbiomac.2020.03.251
ER  - 

@article{
author = "Stanković, Ivana M. and Blagojević Filipović, Jelena P. and Zarić, Snežana D.",
year = "2020",
abstract = "The geometries of the contacts between monosaccharides and aromatic rings of amino acids found in X-ray crystallography structures, in the Protein Data Bank (PDB), were analyzed, while the energies of the interactions were calculated using quantum chemical method. We found 1913 sugar/aromatic ring contacts, 1054 of them (55%) with CH/π interactions and 859 of them (45%) without CH/π interactions. We showed that only the carbohydrate/aromatic contacts with CH/π interactions are preferentially parallel and enable sliding in the plane parallel to aromatic ring. The calculated interaction energies in systems with CH/π interactions are in the range from −1.7 kcal/mol to −6.8 kcal/mol, while in the systems without CH/π interactions are in the range −0.2 to −3.2 kcal/mol. Hence, the binding that does not include CH/π interactions, can also be important for aromatic amino acid and carbohydrate binding processes, since some of these interactions can be as strong as the CH/π interactions. At the same time, these interactions can be weak enough to enable releasing of small carbohydrate fragments after the enzymatic reaction. The analysis of the protein-substrate patterns showed that every second or third carbohydrate unit in long substrates stacks with protein aromatic amino acids.",
publisher = "Elsevier",
journal = "International Journal of Biological Macromolecules",
title = "Carbohydrate – Protein aromatic ring interactions beyond CH/π interactions: A Protein Data Bank survey and quantum chemical calculations",
volume = "157",
pages = "1-9",
doi = "10.1016/j.ijbiomac.2020.03.251"
}

Stanković, I. M., Blagojević Filipović, J. P.,& Zarić, S. D.. (2020). Carbohydrate – Protein aromatic ring interactions beyond CH/π interactions: A Protein Data Bank survey and quantum chemical calculations. in International Journal of Biological Macromolecules
Elsevier., 157, 1-9.
https://doi.org/10.1016/j.ijbiomac.2020.03.251

Stanković IM, Blagojević Filipović JP, Zarić SD. Carbohydrate – Protein aromatic ring interactions beyond CH/π interactions: A Protein Data Bank survey and quantum chemical calculations. in International Journal of Biological Macromolecules. 2020;157:1-9.
doi:10.1016/j.ijbiomac.2020.03.251 .

Stanković, Ivana M., Blagojević Filipović, Jelena P., Zarić, Snežana D., "Carbohydrate – Protein aromatic ring interactions beyond CH/π interactions: A Protein Data Bank survey and quantum chemical calculations" in International Journal of Biological Macromolecules, 157 (2020):1-9,
https://doi.org/10.1016/j.ijbiomac.2020.03.251 . .

TY  - JOUR
AU  - Stanković, Ivana M.
AU  - Blagojević Filipović, Jelena P.
AU  - Zarić, Snežana D.
PY  - 2020
UR  - https://cherry.chem.bg.ac.rs/handle/123456789/3984
AB  - The geometries of the contacts between monosaccharides and aromatic rings of amino acids found in X-ray crystallography structures, in the Protein Data Bank (PDB), were analyzed, while the energies of the interactions were calculated using quantum chemical method. We found 1913 sugar/aromatic ring contacts, 1054 of them (55%) with CH/π interactions and 859 of them (45%) without CH/π interactions. We showed that only the carbohydrate/aromatic contacts with CH/π interactions are preferentially parallel and enable sliding in the plane parallel to aromatic ring. The calculated interaction energies in systems with CH/π interactions are in the range from −1.7 kcal/mol to −6.8 kcal/mol, while in the systems without CH/π interactions are in the range −0.2 to −3.2 kcal/mol. Hence, the binding that does not include CH/π interactions, can also be important for aromatic amino acid and carbohydrate binding processes, since some of these interactions can be as strong as the CH/π interactions. At the same time, these interactions can be weak enough to enable releasing of small carbohydrate fragments after the enzymatic reaction. The analysis of the protein-substrate patterns showed that every second or third carbohydrate unit in long substrates stacks with protein aromatic amino acids.
PB  - Elsevier
T2  - International Journal of Biological Macromolecules
T1  - Carbohydrate – Protein aromatic ring interactions beyond CH/π interactions: A Protein Data Bank survey and quantum chemical calculations
VL  - 157
SP  - 1
EP  - 9
DO  - 10.1016/j.ijbiomac.2020.03.251
ER  - 

@article{
author = "Stanković, Ivana M. and Blagojević Filipović, Jelena P. and Zarić, Snežana D.",
year = "2020",
abstract = "The geometries of the contacts between monosaccharides and aromatic rings of amino acids found in X-ray crystallography structures, in the Protein Data Bank (PDB), were analyzed, while the energies of the interactions were calculated using quantum chemical method. We found 1913 sugar/aromatic ring contacts, 1054 of them (55%) with CH/π interactions and 859 of them (45%) without CH/π interactions. We showed that only the carbohydrate/aromatic contacts with CH/π interactions are preferentially parallel and enable sliding in the plane parallel to aromatic ring. The calculated interaction energies in systems with CH/π interactions are in the range from −1.7 kcal/mol to −6.8 kcal/mol, while in the systems without CH/π interactions are in the range −0.2 to −3.2 kcal/mol. Hence, the binding that does not include CH/π interactions, can also be important for aromatic amino acid and carbohydrate binding processes, since some of these interactions can be as strong as the CH/π interactions. At the same time, these interactions can be weak enough to enable releasing of small carbohydrate fragments after the enzymatic reaction. The analysis of the protein-substrate patterns showed that every second or third carbohydrate unit in long substrates stacks with protein aromatic amino acids.",
publisher = "Elsevier",
journal = "International Journal of Biological Macromolecules",
title = "Carbohydrate – Protein aromatic ring interactions beyond CH/π interactions: A Protein Data Bank survey and quantum chemical calculations",
volume = "157",
pages = "1-9",
doi = "10.1016/j.ijbiomac.2020.03.251"
}

Stanković, I. M., Blagojević Filipović, J. P.,& Zarić, S. D.. (2020). Carbohydrate – Protein aromatic ring interactions beyond CH/π interactions: A Protein Data Bank survey and quantum chemical calculations. in International Journal of Biological Macromolecules
Elsevier., 157, 1-9.
https://doi.org/10.1016/j.ijbiomac.2020.03.251

Stanković IM, Blagojević Filipović JP, Zarić SD. Carbohydrate – Protein aromatic ring interactions beyond CH/π interactions: A Protein Data Bank survey and quantum chemical calculations. in International Journal of Biological Macromolecules. 2020;157:1-9.
doi:10.1016/j.ijbiomac.2020.03.251 .

Stanković, Ivana M., Blagojević Filipović, Jelena P., Zarić, Snežana D., "Carbohydrate – Protein aromatic ring interactions beyond CH/π interactions: A Protein Data Bank survey and quantum chemical calculations" in International Journal of Biological Macromolecules, 157 (2020):1-9,
https://doi.org/10.1016/j.ijbiomac.2020.03.251 . .

TY  - DATA
AU  - Stanković, Ivana M.
AU  - Blagojević Filipović, Jelena P.
AU  - Zarić, Snežana D.
PY  - 2020
UR  - https://cherry.chem.bg.ac.rs/handle/123456789/3987
PB  - Elsevier
T2  - International Journal of Biological Macromolecules
T1  - Supplementary material for the article: Stanković, I. M.; Blagojević Filipović, J. P.; Zarić, S. D. Carbohydrate – Protein Aromatic Ring Interactions beyond CH/π Interactions: A Protein Data Bank Survey and Quantum Chemical Calculations. Int. J. Biol. Macromol. 2020, 157, 1–9. https://doi.org/10.1016/j.ijbiomac.2020.03.251
UR  - https://hdl.handle.net/21.15107/rcub_cherry_3987
ER  - 

@misc{
author = "Stanković, Ivana M. and Blagojević Filipović, Jelena P. and Zarić, Snežana D.",
year = "2020",
publisher = "Elsevier",
journal = "International Journal of Biological Macromolecules",
title = "Supplementary material for the article: Stanković, I. M.; Blagojević Filipović, J. P.; Zarić, S. D. Carbohydrate – Protein Aromatic Ring Interactions beyond CH/π Interactions: A Protein Data Bank Survey and Quantum Chemical Calculations. Int. J. Biol. Macromol. 2020, 157, 1–9. https://doi.org/10.1016/j.ijbiomac.2020.03.251",
url = "https://hdl.handle.net/21.15107/rcub_cherry_3987"
}

Stanković, I. M., Blagojević Filipović, J. P.,& Zarić, S. D.. (2020). Supplementary material for the article: Stanković, I. M.; Blagojević Filipović, J. P.; Zarić, S. D. Carbohydrate – Protein Aromatic Ring Interactions beyond CH/π Interactions: A Protein Data Bank Survey and Quantum Chemical Calculations. Int. J. Biol. Macromol. 2020, 157, 1–9. https://doi.org/10.1016/j.ijbiomac.2020.03.251. in International Journal of Biological Macromolecules
Elsevier..
https://hdl.handle.net/21.15107/rcub_cherry_3987

Stanković IM, Blagojević Filipović JP, Zarić SD. Supplementary material for the article: Stanković, I. M.; Blagojević Filipović, J. P.; Zarić, S. D. Carbohydrate – Protein Aromatic Ring Interactions beyond CH/π Interactions: A Protein Data Bank Survey and Quantum Chemical Calculations. Int. J. Biol. Macromol. 2020, 157, 1–9. https://doi.org/10.1016/j.ijbiomac.2020.03.251. in International Journal of Biological Macromolecules. 2020;.
https://hdl.handle.net/21.15107/rcub_cherry_3987 .

Stanković, Ivana M., Blagojević Filipović, Jelena P., Zarić, Snežana D., "Supplementary material for the article: Stanković, I. M.; Blagojević Filipović, J. P.; Zarić, S. D. Carbohydrate – Protein Aromatic Ring Interactions beyond CH/π Interactions: A Protein Data Bank Survey and Quantum Chemical Calculations. Int. J. Biol. Macromol. 2020, 157, 1–9. https://doi.org/10.1016/j.ijbiomac.2020.03.251" in International Journal of Biological Macromolecules (2020),
https://hdl.handle.net/21.15107/rcub_cherry_3987 .

TY  - CONF
AU  - Ninković, Dragan B.
AU  - Malenov, Dušan P.
AU  - Blagojević Filipović, Jelena P.
AU  - Živković, Jelena M.
AU  - Zarić, Snežana D.
PY  - 2019
UR  - http://cherry.chem.bg.ac.rs/handle/123456789/6369
C3  - 1st International Conference on Noncovalent Interactions (ICNI-2019)
T1  - π-π interactions in organic, coordination, and organometallic compounds
UR  - https://hdl.handle.net/21.15107/rcub_cherry_6369
ER  - 

@conference{
author = "Ninković, Dragan B. and Malenov, Dušan P. and Blagojević Filipović, Jelena P. and Živković, Jelena M. and Zarić, Snežana D.",
year = "2019",
journal = "1st International Conference on Noncovalent Interactions (ICNI-2019)",
title = "π-π interactions in organic, coordination, and organometallic compounds",
url = "https://hdl.handle.net/21.15107/rcub_cherry_6369"
}

Ninković, D. B., Malenov, D. P., Blagojević Filipović, J. P., Živković, J. M.,& Zarić, S. D.. (2019). π-π interactions in organic, coordination, and organometallic compounds. in 1st International Conference on Noncovalent Interactions (ICNI-2019).
https://hdl.handle.net/21.15107/rcub_cherry_6369

Ninković DB, Malenov DP, Blagojević Filipović JP, Živković JM, Zarić SD. π-π interactions in organic, coordination, and organometallic compounds. in 1st International Conference on Noncovalent Interactions (ICNI-2019). 2019;.
https://hdl.handle.net/21.15107/rcub_cherry_6369 .

Ninković, Dragan B., Malenov, Dušan P., Blagojević Filipović, Jelena P., Živković, Jelena M., Zarić, Snežana D., "π-π interactions in organic, coordination, and organometallic compounds" in 1st International Conference on Noncovalent Interactions (ICNI-2019) (2019),
https://hdl.handle.net/21.15107/rcub_cherry_6369 .

TY  - CONF
AU  - Ninković, Dragan
AU  - Veljković, Dušan Ž.
AU  - Malenov, Dušan P.
AU  - Milovanović, Milan R.
AU  - Živković, Jelena M.
AU  - Stanković, Ivana M.
AU  - Veljković, Ivana S.
AU  - Medaković, Vesna
AU  - Blagojević Filipović, Jelena P.
AU  - Vojislavljević-Vasilev, Dubravka
AU  - Zarić, Snežana D.
PY  - 2019
UR  - http://cherry.chem.bg.ac.rs/handle/123456789/5266
AB  - Наше истраживање се заснива на анализи података у кристалним структурама
из Кембичке базе структурних података (CSD) и на квантнo хемијским
прорачунима. Анализа података из CSD-а омогућава да се препознају интеракције у
кристалним структурама и да се опишу геометрије ових интеракција, док помоћу
квантно-хемијских прорачуна можемо проценити интеракционе енергије и пронаћи
најстабилније геометрије интеракција. Користећи ову методологију успели смо да
препознамо и опишемо неколико нових типова интеракција.
Наше проучавање интеракција планарних метал-хелатних прстенова показало је
могућност стекинг интеракција са органским ароматичним прстеновима и
интеракције између два хелатна прстена. Израчунате енергије указују на јаке
стекинг интеракције метал-хелатних прстенова; стекинг метал-хелатних прстенова
је јачи од стекинга између два молекула бензена. Испитивања интеракција
координираних молекула воде и амонијака указују на јаче водоничне везе и јаче
ОH/π и NH/π интеракције координираних у односу на некоординоване молекуле
воде и амонијака. Прорачуни ОH/М интеракција између металног јона у квадратнo
планарним комплексима и молекулa воде указују да су ове интеракције међу
најјачим водоничним везама у било ком молекулском систему.
Студије о ароматичним молекулима указују на стекинг интеракције са великим
хоризонталним померањима између два ароматична молекула са значајно јаким
интеракцијама, енергија је 70% најјаче стекинг интеракције. Наши подаци такође
указују на то да су интеракције алифатичних прстенова са ароматичним прстеном
јаче од интеракција између два ароматична молекула, док су
алифатично/ароматичне интеракције веома честе у протеинским структурама.
AB  - Our research is based on analyzing data in crystal structures from the Cambridge
Structural Database (CSD) and on quantum chemical calculations. The analysis of the
data from the CSD enable to recognize interactions in crystal structures and to describe
the geometries of these interactions, while by quantum chemical calculations we can
evaluate interaction energies and find the most stable interaction geometries. Using this
methodology we were able to recognize and describe several new types of noncovalent
interactions.
Our study of planar metal-chelate rings interactions showed possibility of chelate ring
stacking interactions with organic aromatic rings, and stacking interactions between two
chelate rings. The calculated energies indicate strong stacking interactions of metalchelate rings; the stacking of metal-chelate rings is stronger than stacking between two
benzene molecules. Studies of interactions of coordinated water and ammonia indicate
stronger hydrogen bonds and stronger OH/π and NH/π interactions of coordinated in
comparison to noncoordianted water and ammonia. 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.
The studies on aromatic molecules indicate stacking interactions at large horizontal
dispacements between two aromatic molecules with significantly strong interacitons, the
energy is 70% of the strongest stacking geometry. Our data also indicate that stacking
interactions of an aliphatic rings with an aromatic ring are stonger than interactions between two aromatic molecules, while aliphatic/aromatic interactions are very frequent in
protein structures.
PB  - Српско кристалографско друштво
C3  - XXVI Конференција Српског кристалографског друштва, Књига апстраката
T1  - Нековалентне интеракције комплекса метала и ароматичних молекула
T1  - Noncovalent interactions of metal complexes and aromatic molecules
UR  - https://hdl.handle.net/21.15107/rcub_cherry_5266
ER  - 

@conference{
author = "Ninković, Dragan and Veljković, Dušan Ž. and Malenov, Dušan P. and Milovanović, Milan R. and Živković, Jelena M. and Stanković, Ivana M. and Veljković, Ivana S. and Medaković, Vesna and Blagojević Filipović, Jelena P. and Vojislavljević-Vasilev, Dubravka and Zarić, Snežana D.",
year = "2019",
abstract = "Наше истраживање се заснива на анализи података у кристалним структурама
из Кембичке базе структурних података (CSD) и на квантнo хемијским
прорачунима. Анализа података из CSD-а омогућава да се препознају интеракције у
кристалним структурама и да се опишу геометрије ових интеракција, док помоћу
квантно-хемијских прорачуна можемо проценити интеракционе енергије и пронаћи
најстабилније геометрије интеракција. Користећи ову методологију успели смо да
препознамо и опишемо неколико нових типова интеракција.
Наше проучавање интеракција планарних метал-хелатних прстенова показало је
могућност стекинг интеракција са органским ароматичним прстеновима и
интеракције између два хелатна прстена. Израчунате енергије указују на јаке
стекинг интеракције метал-хелатних прстенова; стекинг метал-хелатних прстенова
је јачи од стекинга између два молекула бензена. Испитивања интеракција
координираних молекула воде и амонијака указују на јаче водоничне везе и јаче
ОH/π и NH/π интеракције координираних у односу на некоординоване молекуле
воде и амонијака. Прорачуни ОH/М интеракција између металног јона у квадратнo
планарним комплексима и молекулa воде указују да су ове интеракције међу
најјачим водоничним везама у било ком молекулском систему.
Студије о ароматичним молекулима указују на стекинг интеракције са великим
хоризонталним померањима између два ароматична молекула са значајно јаким
интеракцијама, енергија је 70% најјаче стекинг интеракције. Наши подаци такође
указују на то да су интеракције алифатичних прстенова са ароматичним прстеном
јаче од интеракција између два ароматична молекула, док су
алифатично/ароматичне интеракције веома честе у протеинским структурама., Our research is based on analyzing data in crystal structures from the Cambridge
Structural Database (CSD) and on quantum chemical calculations. The analysis of the
data from the CSD enable to recognize interactions in crystal structures and to describe
the geometries of these interactions, while by quantum chemical calculations we can
evaluate interaction energies and find the most stable interaction geometries. Using this
methodology we were able to recognize and describe several new types of noncovalent
interactions.
Our study of planar metal-chelate rings interactions showed possibility of chelate ring
stacking interactions with organic aromatic rings, and stacking interactions between two
chelate rings. The calculated energies indicate strong stacking interactions of metalchelate rings; the stacking of metal-chelate rings is stronger than stacking between two
benzene molecules. Studies of interactions of coordinated water and ammonia indicate
stronger hydrogen bonds and stronger OH/π and NH/π interactions of coordinated in
comparison to noncoordianted water and ammonia. 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.
The studies on aromatic molecules indicate stacking interactions at large horizontal
dispacements between two aromatic molecules with significantly strong interacitons, the
energy is 70% of the strongest stacking geometry. Our data also indicate that stacking
interactions of an aliphatic rings with an aromatic ring are stonger than interactions between two aromatic molecules, while aliphatic/aromatic interactions are very frequent in
protein structures.",
publisher = "Српско кристалографско друштво",
journal = "XXVI Конференција Српског кристалографског друштва, Књига апстраката",
title = "Нековалентне интеракције комплекса метала и ароматичних молекула, Noncovalent interactions of metal complexes and aromatic molecules",
url = "https://hdl.handle.net/21.15107/rcub_cherry_5266"
}

Ninković, D., Veljković, D. Ž., Malenov, D. P., Milovanović, M. R., Živković, J. M., Stanković, I. M., Veljković, I. S., Medaković, V., Blagojević Filipović, J. P., Vojislavljević-Vasilev, D.,& Zarić, S. D.. (2019). Нековалентне интеракције комплекса метала и ароматичних молекула. in XXVI Конференција Српског кристалографског друштва, Књига апстраката
Српско кристалографско друштво..
https://hdl.handle.net/21.15107/rcub_cherry_5266

Ninković D, Veljković DŽ, Malenov DP, Milovanović MR, Živković JM, Stanković IM, Veljković IS, Medaković V, Blagojević Filipović JP, Vojislavljević-Vasilev D, Zarić SD. Нековалентне интеракције комплекса метала и ароматичних молекула. in XXVI Конференција Српског кристалографског друштва, Књига апстраката. 2019;.
https://hdl.handle.net/21.15107/rcub_cherry_5266 .

Ninković, Dragan, Veljković, Dušan Ž., Malenov, Dušan P., Milovanović, Milan R., Živković, Jelena M., Stanković, Ivana M., Veljković, Ivana S., Medaković, Vesna, Blagojević Filipović, Jelena P., Vojislavljević-Vasilev, Dubravka, Zarić, Snežana D., "Нековалентне интеракције комплекса метала и ароматичних молекула" in XXVI Конференција Српског кристалографског друштва, Књига апстраката (2019),
https://hdl.handle.net/21.15107/rcub_cherry_5266 .

TY  - CONF
AU  - Blagojević Filipović, Jelena P.
AU  - Zarić, Snežana D.
PY  - 2019
UR  - http://cherry.chem.bg.ac.rs/handle/123456789/5271
AB  - The arrangement corresponding to stacking interactions is observed in crystal
structures of six-membered resonance-assisted hydrogen-bridged rings (RAHB) [1] and
five-membered saturated hydrogen-bridged rings [2]
- 91% and 86% of all contacts in
Cambridge Structural Database (CSD), respectively, with preferentially antiparallel
orientation (Figure 1). Stacking arrangement is also observed in crystal structures
between six-membered RAHB and C6-aromatic rings (59% of all contacts in CSD) and
between five-membered saturated hydrogen-bridged rings and C6-aromatic rings [3]
(45% of all contacts in CSD).
Interaction energies, calculated on dimer model systems in the gas phase at
CCSD(T)/CBS level, are relatively strong. They are similar for RAHB/RAHB dimers [1]
and saturated hydrogen-bridged ring dimers [2] (up to -4.7 kcal/mol and -4.9 kcal/mol,
respectively). Difference is larger between interaction energies of RAHB/benzene and
saturated hydrogen-bridged ring/benzene dimers [3] (up to -3.5 kcal/mol and -4.4
kcal/mol, respectively). These findings can be usefull for widening the concept of
stacking interactions, since stacking interactions of saturated hydrogen-bridged systems
were recently observed [2,3] and also in the design of supramolecular structures involving
hydrogen-bridged rings.
C3  - 1st International Conferences on Noncovalent Interactions (ICNI-2019)
T1  - Stacking Interactions of Planar Hydrogen-Bridged Rings
UR  - https://hdl.handle.net/21.15107/rcub_cherry_5271
ER  - 

@conference{
author = "Blagojević Filipović, Jelena P. and Zarić, Snežana D.",
year = "2019",
abstract = "The arrangement corresponding to stacking interactions is observed in crystal
structures of six-membered resonance-assisted hydrogen-bridged rings (RAHB) [1] and
five-membered saturated hydrogen-bridged rings [2]
- 91% and 86% of all contacts in
Cambridge Structural Database (CSD), respectively, with preferentially antiparallel
orientation (Figure 1). Stacking arrangement is also observed in crystal structures
between six-membered RAHB and C6-aromatic rings (59% of all contacts in CSD) and
between five-membered saturated hydrogen-bridged rings and C6-aromatic rings [3]
(45% of all contacts in CSD).
Interaction energies, calculated on dimer model systems in the gas phase at
CCSD(T)/CBS level, are relatively strong. They are similar for RAHB/RAHB dimers [1]
and saturated hydrogen-bridged ring dimers [2] (up to -4.7 kcal/mol and -4.9 kcal/mol,
respectively). Difference is larger between interaction energies of RAHB/benzene and
saturated hydrogen-bridged ring/benzene dimers [3] (up to -3.5 kcal/mol and -4.4
kcal/mol, respectively). These findings can be usefull for widening the concept of
stacking interactions, since stacking interactions of saturated hydrogen-bridged systems
were recently observed [2,3] and also in the design of supramolecular structures involving
hydrogen-bridged rings.",
journal = "1st International Conferences on Noncovalent Interactions (ICNI-2019)",
title = "Stacking Interactions of Planar Hydrogen-Bridged Rings",
url = "https://hdl.handle.net/21.15107/rcub_cherry_5271"
}

Blagojević Filipović, J. P.,& Zarić, S. D.. (2019). Stacking Interactions of Planar Hydrogen-Bridged Rings. in 1st International Conferences on Noncovalent Interactions (ICNI-2019).
https://hdl.handle.net/21.15107/rcub_cherry_5271

Blagojević Filipović JP, Zarić SD. Stacking Interactions of Planar Hydrogen-Bridged Rings. in 1st International Conferences on Noncovalent Interactions (ICNI-2019). 2019;.
https://hdl.handle.net/21.15107/rcub_cherry_5271 .

Blagojević Filipović, Jelena P., Zarić, Snežana D., "Stacking Interactions of Planar Hydrogen-Bridged Rings" in 1st International Conferences on Noncovalent Interactions (ICNI-2019) (2019),
https://hdl.handle.net/21.15107/rcub_cherry_5271 .

TY  - CONF
AU  - Blagojević Filipović, Jelena P.
AU  - Zarić, Snežana D.
PY  - 2019
UR  - http://cherry.chem.bg.ac.rs/handle/123456789/5276
AB  - У Кембричкој бази структурних података паралелни контакти чине 59,4%
контаката између С6-ароматичних прстенова и шесточланих прстенова формираних
водоничном везом потпомогнутом резонанцијом. Растојања у кристалним
структурама између паралелних равни ових прстенова одговарају растојањима
карактеристичним за стекинг интеракције (3,0–4,0 Å).
Квантнохемијски прорачуни енергија интеракције на модел-системима, који су
засновани на учесталости у кристалним структурама, показују да се енергије
најстабилнијих интеракција налазе у опсегу од –3,2 до –3,5 kcal/mol. Ове
интеракције су нешто слабије од међусобних интеракција шесточланих прстенова
формираних водоничном везом потпомогнутом резонанцијом (–4,7 kcal/mol) [1],
међусобних интеракција засићених петочланих прстенова формираних водоничном
везом (–4,9 kcal/mol) [2], као и интеракција засићених петочланих прстенова
формираних водоничном везом и С6-ароматичних прстенова (–4,4 kcal/mol) [3].
Ипак, оне су довољно јаке да би могле бити врло корисне у дизајнирању
кристалних структура.
AB  - Parallel contacts form 59.4% of contacts between C6-aromatic rings and sixmembered resonance-assisted hydrogen-bridged rings found in Cambridge Structural
Database. Distances between parallel planes of these rings in crystal structures correspond to distances typical for stacking interactions (3.0–4.0 Å).
Quantum chemical calculations of interaction energies, performed on model systems
based on abundance in crystal structures, show that the stongest interactions are in the
range between –3.2 kcal/mol and –3.5 kcal/mol. These interactions are somewhat weaker
than mutual interactions between six-membered resonance-assisted hydrogen-bridged
rings (–4.7 kcal/mol) [1], mutual interactions of saturated five-membered hydrogenbridged rings (–4.9 kcal/mol) [2], as well as the interations between saturated fivemembered hydrogen-bridged rings and C6-aromatic rings (–4.4 kcal/mol) [3]. However,
they are strong enough to be possibly very useful in crystal engineering.
C3  - XXVI Conference of Serbian Crystallographic Society
T1  - Stacking Interactions of С6-aromatic rings and six-memberd resonance-assisted hydrogen-bridged rings
T1  - Стекинг интеракције C6-ароматичних прстенова и шесточланих прстенова формираних водоничном езом потпомогнутом резонанцијом
UR  - https://hdl.handle.net/21.15107/rcub_cherry_5276
ER  - 

@conference{
author = "Blagojević Filipović, Jelena P. and Zarić, Snežana D.",
year = "2019",
abstract = "У Кембричкој бази структурних података паралелни контакти чине 59,4%
контаката између С6-ароматичних прстенова и шесточланих прстенова формираних
водоничном везом потпомогнутом резонанцијом. Растојања у кристалним
структурама између паралелних равни ових прстенова одговарају растојањима
карактеристичним за стекинг интеракције (3,0–4,0 Å).
Квантнохемијски прорачуни енергија интеракције на модел-системима, који су
засновани на учесталости у кристалним структурама, показују да се енергије
најстабилнијих интеракција налазе у опсегу од –3,2 до –3,5 kcal/mol. Ове
интеракције су нешто слабије од међусобних интеракција шесточланих прстенова
формираних водоничном везом потпомогнутом резонанцијом (–4,7 kcal/mol) [1],
међусобних интеракција засићених петочланих прстенова формираних водоничном
везом (–4,9 kcal/mol) [2], као и интеракција засићених петочланих прстенова
формираних водоничном везом и С6-ароматичних прстенова (–4,4 kcal/mol) [3].
Ипак, оне су довољно јаке да би могле бити врло корисне у дизајнирању
кристалних структура., Parallel contacts form 59.4% of contacts between C6-aromatic rings and sixmembered resonance-assisted hydrogen-bridged rings found in Cambridge Structural
Database. Distances between parallel planes of these rings in crystal structures correspond to distances typical for stacking interactions (3.0–4.0 Å).
Quantum chemical calculations of interaction energies, performed on model systems
based on abundance in crystal structures, show that the stongest interactions are in the
range between –3.2 kcal/mol and –3.5 kcal/mol. These interactions are somewhat weaker
than mutual interactions between six-membered resonance-assisted hydrogen-bridged
rings (–4.7 kcal/mol) [1], mutual interactions of saturated five-membered hydrogenbridged rings (–4.9 kcal/mol) [2], as well as the interations between saturated fivemembered hydrogen-bridged rings and C6-aromatic rings (–4.4 kcal/mol) [3]. However,
they are strong enough to be possibly very useful in crystal engineering.",
journal = "XXVI Conference of Serbian Crystallographic Society",
title = "Stacking Interactions of С6-aromatic rings and six-memberd resonance-assisted hydrogen-bridged rings, Стекинг интеракције C6-ароматичних прстенова и шесточланих прстенова формираних водоничном езом потпомогнутом резонанцијом",
url = "https://hdl.handle.net/21.15107/rcub_cherry_5276"
}

Blagojević Filipović, J. P.,& Zarić, S. D.. (2019). Stacking Interactions of С6-aromatic rings and six-memberd resonance-assisted hydrogen-bridged rings. in XXVI Conference of Serbian Crystallographic Society.
https://hdl.handle.net/21.15107/rcub_cherry_5276

Blagojević Filipović JP, Zarić SD. Stacking Interactions of С6-aromatic rings and six-memberd resonance-assisted hydrogen-bridged rings. in XXVI Conference of Serbian Crystallographic Society. 2019;.
https://hdl.handle.net/21.15107/rcub_cherry_5276 .

Blagojević Filipović, Jelena P., Zarić, Snežana D., "Stacking Interactions of С6-aromatic rings and six-memberd resonance-assisted hydrogen-bridged rings" in XXVI Conference of Serbian Crystallographic Society (2019),
https://hdl.handle.net/21.15107/rcub_cherry_5276 .

TY  - CONF
AU  - Blagojević Filipović, Jelena P.
AU  - Zarić, Snežana D.
PY  - 2019
UR  - http://cherry.chem.bg.ac.rs/handle/123456789/5272
AB  - Mutual contacts between resonance-assisted hydrogen-bridged (RAHB) rings,1
as
well as contacts between RAHB rings and C6
-aromatic rings2
are systematically
analyzed by searching Cambridge Structural Database (CSD) (Fig. 1) It is observed
that the tendency of forming stacking interactions is very high in RAHB/RAHB
contacts, since 91% of them corresponds to stacked arrangement. At the other side,
the tendency of forming stacked contacts is not so pronounced in RAHB/C6
-
aromatic contacts, although the majority of them (59%) corresponds also to
stacking. The high level quantum-chemical calculations (CCSD(T)/CBS) are
performed on model systems that are based on abundance in CSD. The energies of
the strongest calculated RAHB/RAHB stacking interactions can reach -4.7
kcal/mol. The strongest calculated RAHB/benzene stacking interactions are weaker
(-3.7 kcal/mol), but they can be also stronger than the corresponding RAHB/RAHB
stacking interactions, depending on the RAHB system considered.
C3  - 7th Conference of the Young Chemists of Serbia
T1  - Crystallographic and quantum-chemical study of stacking interactions of resonance-assisted hydrogen-bridged rings
UR  - https://hdl.handle.net/21.15107/rcub_cherry_5272
ER  - 

@conference{
author = "Blagojević Filipović, Jelena P. and Zarić, Snežana D.",
year = "2019",
abstract = "Mutual contacts between resonance-assisted hydrogen-bridged (RAHB) rings,1
as
well as contacts between RAHB rings and C6
-aromatic rings2
are systematically
analyzed by searching Cambridge Structural Database (CSD) (Fig. 1) It is observed
that the tendency of forming stacking interactions is very high in RAHB/RAHB
contacts, since 91% of them corresponds to stacked arrangement. At the other side,
the tendency of forming stacked contacts is not so pronounced in RAHB/C6
-
aromatic contacts, although the majority of them (59%) corresponds also to
stacking. The high level quantum-chemical calculations (CCSD(T)/CBS) are
performed on model systems that are based on abundance in CSD. The energies of
the strongest calculated RAHB/RAHB stacking interactions can reach -4.7
kcal/mol. The strongest calculated RAHB/benzene stacking interactions are weaker
(-3.7 kcal/mol), but they can be also stronger than the corresponding RAHB/RAHB
stacking interactions, depending on the RAHB system considered.",
journal = "7th Conference of the Young Chemists of Serbia",
title = "Crystallographic and quantum-chemical study of stacking interactions of resonance-assisted hydrogen-bridged rings",
url = "https://hdl.handle.net/21.15107/rcub_cherry_5272"
}

Blagojević Filipović, J. P.,& Zarić, S. D.. (2019). Crystallographic and quantum-chemical study of stacking interactions of resonance-assisted hydrogen-bridged rings. in 7th Conference of the Young Chemists of Serbia.
https://hdl.handle.net/21.15107/rcub_cherry_5272

Blagojević Filipović JP, Zarić SD. Crystallographic and quantum-chemical study of stacking interactions of resonance-assisted hydrogen-bridged rings. in 7th Conference of the Young Chemists of Serbia. 2019;.
https://hdl.handle.net/21.15107/rcub_cherry_5272 .

Blagojević Filipović, Jelena P., Zarić, Snežana D., "Crystallographic and quantum-chemical study of stacking interactions of resonance-assisted hydrogen-bridged rings" in 7th Conference of the Young Chemists of Serbia (2019),
https://hdl.handle.net/21.15107/rcub_cherry_5272 .