TY  - JOUR
AU  - Baranac-Stojanović, Marija
PY  - 2020
UR  - https://cherry.chem.bg.ac.rs/handle/123456789/4027
AB  - Density functional theory calculations have been performed to explore the substituent effect on benzene's structure and aromaticity upon excitation to the first triplet excited state (T1). Discussion is based on spin density analysis, HOMA (harmonic oscillator model of aromaticity), NICS (nucleus-independent chemical shift), ACID (anisotropy of the induced current density), and monohydrogenation free energies and shows that a large span of aromatic properties, from highly antiaromatic to strongly aromatic, could be achieved by varying the substituent. This opens up a possibility of controlling benzene's physicochemical behavior in its excited state, while molecular motion, predicted for several derivatives, could be of interest for the development of photomechanical materials.
PB  - American Chemical Society
T2  - The Journal of Organic Chemistry
T1  - Substituent Effect on Triplet State Aromaticity of Benzene
VL  - 85
IS  - 6
SP  - 4289
EP  - 4297
DO  - 10.1021/acs.joc.9b03472
ER  - 

@article{
author = "Baranac-Stojanović, Marija",
year = "2020",
abstract = "Density functional theory calculations have been performed to explore the substituent effect on benzene's structure and aromaticity upon excitation to the first triplet excited state (T1). Discussion is based on spin density analysis, HOMA (harmonic oscillator model of aromaticity), NICS (nucleus-independent chemical shift), ACID (anisotropy of the induced current density), and monohydrogenation free energies and shows that a large span of aromatic properties, from highly antiaromatic to strongly aromatic, could be achieved by varying the substituent. This opens up a possibility of controlling benzene's physicochemical behavior in its excited state, while molecular motion, predicted for several derivatives, could be of interest for the development of photomechanical materials.",
publisher = "American Chemical Society",
journal = "The Journal of Organic Chemistry",
title = "Substituent Effect on Triplet State Aromaticity of Benzene",
volume = "85",
number = "6",
pages = "4289-4297",
doi = "10.1021/acs.joc.9b03472"
}

Baranac-Stojanović, M.. (2020). Substituent Effect on Triplet State Aromaticity of Benzene. in The Journal of Organic Chemistry
American Chemical Society., 85(6), 4289-4297.
https://doi.org/10.1021/acs.joc.9b03472

Baranac-Stojanović M. Substituent Effect on Triplet State Aromaticity of Benzene. in The Journal of Organic Chemistry. 2020;85(6):4289-4297.
doi:10.1021/acs.joc.9b03472 .

Baranac-Stojanović, Marija, "Substituent Effect on Triplet State Aromaticity of Benzene" in The Journal of Organic Chemistry, 85, no. 6 (2020):4289-4297,
https://doi.org/10.1021/acs.joc.9b03472 . .

TY  - JOUR
AU  - Baranac-Stojanović, Marija
AU  - Stojanović, Milovan
PY  - 2019
UR  - https://cherry.chem.bg.ac.rs/handle/123456789/2847
AB  - The effect of two types of dibenzo-fusion of pentalene in the singlet and triplet states on its molecular energies and magnetically induced ring currents was examined via density functional calculations. The isomerization energy decomposition analysis (IEDA) together with the calculated aromaticity indices (NICS(1) zz , HOMA and FLU π ), estimation of resonance energies (RE) and extra cyclic resonance energies (ECRE) via the NBO method, and the NICS-XY-scans revealed that the π-electronic system is the most important factor controlling the molecular energies. The [a,f] topology features greater delocalization, which results in two opposing effects: larger ECRE, but weaker π-bonding. The latter is mainly responsible for the higher energy of [a,f]-dibenzopentalene (DBP) (ΔE iso = 21.7 kcal mol -1 ), with the other effects being σ-orbital and electrostatic interactions. The reversal of energetic stability in the triplet states (ΔE iso = -10.8 kcal mol -1 ) mainly comes from the reduced Pauli repulsion in [a,f]-DBP, which stabilizes the unpaired spin density over the central trimethylenemethane subunit vs. the central pentalene subunit in [a,e]-DBP. Although the [a,e] topology only reduces the diatropic and paratropic currents of the elementary subunits, benzene and pentalene, the [a,f] topology also creates strong global paratropicity involving the benzene rings. Both DBP isomers are characterized by global and smaller semi-global and local diatropic currents in the triplet state.
PB  - Royal Society of Chemistry
T2  - Physical Chemistry Chemical Physics
T1  - The effect of two types of dibenzoannulation of pentalene on molecular energies and magnetically induced currents
VL  - 21
IS  - 6
SP  - 3250
EP  - 3263
DO  - 10.1039/c8cp07875k
ER  - 

@article{
author = "Baranac-Stojanović, Marija and Stojanović, Milovan",
year = "2019",
abstract = "The effect of two types of dibenzo-fusion of pentalene in the singlet and triplet states on its molecular energies and magnetically induced ring currents was examined via density functional calculations. The isomerization energy decomposition analysis (IEDA) together with the calculated aromaticity indices (NICS(1) zz , HOMA and FLU π ), estimation of resonance energies (RE) and extra cyclic resonance energies (ECRE) via the NBO method, and the NICS-XY-scans revealed that the π-electronic system is the most important factor controlling the molecular energies. The [a,f] topology features greater delocalization, which results in two opposing effects: larger ECRE, but weaker π-bonding. The latter is mainly responsible for the higher energy of [a,f]-dibenzopentalene (DBP) (ΔE iso = 21.7 kcal mol -1 ), with the other effects being σ-orbital and electrostatic interactions. The reversal of energetic stability in the triplet states (ΔE iso = -10.8 kcal mol -1 ) mainly comes from the reduced Pauli repulsion in [a,f]-DBP, which stabilizes the unpaired spin density over the central trimethylenemethane subunit vs. the central pentalene subunit in [a,e]-DBP. Although the [a,e] topology only reduces the diatropic and paratropic currents of the elementary subunits, benzene and pentalene, the [a,f] topology also creates strong global paratropicity involving the benzene rings. Both DBP isomers are characterized by global and smaller semi-global and local diatropic currents in the triplet state.",
publisher = "Royal Society of Chemistry",
journal = "Physical Chemistry Chemical Physics",
title = "The effect of two types of dibenzoannulation of pentalene on molecular energies and magnetically induced currents",
volume = "21",
number = "6",
pages = "3250-3263",
doi = "10.1039/c8cp07875k"
}

Baranac-Stojanović, M.,& Stojanović, M.. (2019). The effect of two types of dibenzoannulation of pentalene on molecular energies and magnetically induced currents. in Physical Chemistry Chemical Physics
Royal Society of Chemistry., 21(6), 3250-3263.
https://doi.org/10.1039/c8cp07875k

Baranac-Stojanović M, Stojanović M. The effect of two types of dibenzoannulation of pentalene on molecular energies and magnetically induced currents. in Physical Chemistry Chemical Physics. 2019;21(6):3250-3263.
doi:10.1039/c8cp07875k .

Baranac-Stojanović, Marija, Stojanović, Milovan, "The effect of two types of dibenzoannulation of pentalene on molecular energies and magnetically induced currents" in Physical Chemistry Chemical Physics, 21, no. 6 (2019):3250-3263,
https://doi.org/10.1039/c8cp07875k . .

TY  - JOUR
AU  - Baranac-Stojanović, Marija
AU  - Stojanović, Milovan
PY  - 2019
UR  - https://cherry.chem.bg.ac.rs/handle/123456789/2863
AB  - The effect of two types of dibenzo-fusion of pentalene in the singlet and triplet states on its molecular energies and magnetically induced ring currents was examined via density functional calculations. The isomerization energy decomposition analysis (IEDA) together with the calculated aromaticity indices (NICS(1) zz , HOMA and FLU π ), estimation of resonance energies (RE) and extra cyclic resonance energies (ECRE) via the NBO method, and the NICS-XY-scans revealed that the π-electronic system is the most important factor controlling the molecular energies. The [a,f] topology features greater delocalization, which results in two opposing effects: larger ECRE, but weaker π-bonding. The latter is mainly responsible for the higher energy of [a,f]-dibenzopentalene (DBP) (ΔE iso = 21.7 kcal mol -1 ), with the other effects being σ-orbital and electrostatic interactions. The reversal of energetic stability in the triplet states (ΔE iso = -10.8 kcal mol -1 ) mainly comes from the reduced Pauli repulsion in [a,f]-DBP, which stabilizes the unpaired spin density over the central trimethylenemethane subunit vs. the central pentalene subunit in [a,e]-DBP. Although the [a,e] topology only reduces the diatropic and paratropic currents of the elementary subunits, benzene and pentalene, the [a,f] topology also creates strong global paratropicity involving the benzene rings. Both DBP isomers are characterized by global and smaller semi-global and local diatropic currents in the triplet state.
PB  - Royal Society of Chemistry
T2  - Physical Chemistry Chemical Physics
T1  - The effect of two types of dibenzoannulation of pentalene on molecular energies and magnetically induced currents
VL  - 21
IS  - 6
SP  - 3250
EP  - 3263
DO  - 10.1039/c8cp07875k
ER  - 

@article{
author = "Baranac-Stojanović, Marija and Stojanović, Milovan",
year = "2019",
abstract = "The effect of two types of dibenzo-fusion of pentalene in the singlet and triplet states on its molecular energies and magnetically induced ring currents was examined via density functional calculations. The isomerization energy decomposition analysis (IEDA) together with the calculated aromaticity indices (NICS(1) zz , HOMA and FLU π ), estimation of resonance energies (RE) and extra cyclic resonance energies (ECRE) via the NBO method, and the NICS-XY-scans revealed that the π-electronic system is the most important factor controlling the molecular energies. The [a,f] topology features greater delocalization, which results in two opposing effects: larger ECRE, but weaker π-bonding. The latter is mainly responsible for the higher energy of [a,f]-dibenzopentalene (DBP) (ΔE iso = 21.7 kcal mol -1 ), with the other effects being σ-orbital and electrostatic interactions. The reversal of energetic stability in the triplet states (ΔE iso = -10.8 kcal mol -1 ) mainly comes from the reduced Pauli repulsion in [a,f]-DBP, which stabilizes the unpaired spin density over the central trimethylenemethane subunit vs. the central pentalene subunit in [a,e]-DBP. Although the [a,e] topology only reduces the diatropic and paratropic currents of the elementary subunits, benzene and pentalene, the [a,f] topology also creates strong global paratropicity involving the benzene rings. Both DBP isomers are characterized by global and smaller semi-global and local diatropic currents in the triplet state.",
publisher = "Royal Society of Chemistry",
journal = "Physical Chemistry Chemical Physics",
title = "The effect of two types of dibenzoannulation of pentalene on molecular energies and magnetically induced currents",
volume = "21",
number = "6",
pages = "3250-3263",
doi = "10.1039/c8cp07875k"
}

Baranac-Stojanović, M.,& Stojanović, M.. (2019). The effect of two types of dibenzoannulation of pentalene on molecular energies and magnetically induced currents. in Physical Chemistry Chemical Physics
Royal Society of Chemistry., 21(6), 3250-3263.
https://doi.org/10.1039/c8cp07875k

Baranac-Stojanović M, Stojanović M. The effect of two types of dibenzoannulation of pentalene on molecular energies and magnetically induced currents. in Physical Chemistry Chemical Physics. 2019;21(6):3250-3263.
doi:10.1039/c8cp07875k .

Baranac-Stojanović, Marija, Stojanović, Milovan, "The effect of two types of dibenzoannulation of pentalene on molecular energies and magnetically induced currents" in Physical Chemistry Chemical Physics, 21, no. 6 (2019):3250-3263,
https://doi.org/10.1039/c8cp07875k . .

TY  - JOUR
AU  - Baranac-Stojanović, Marija
AU  - Stojanović, Milovan
PY  - 2019
UR  - https://cherry.chem.bg.ac.rs/handle/123456789/3128
AB  - This work was initiated by the increasing interest in BN/CC isosterism and by the long-lasting interest in the concepts of aromaticity and substituent effects. We have theoretically examined the aromaticity and stability of monosubstituted BN isosters of benzene, the three isomeric azaborines. The results provide insight into the effect of substitution on two basic molecular properties, which are influenced, here, by the substituent effects and by the B/N relationship in the ring. The results, along with other examples in the literature, also warn chemists that the general belief that aromaticity accounts for enhanced thermodynamic stability is not always true. The stability of cyclic, conjugated compounds depends on several effects, and only one of them is aromaticity. In addition, our calculations predict a switching of electronic properties of the NH 2 group from the usual p-electron donor to a π-electron acceptor when it is moved from the B/C atoms to the nitrogen atom in all isomers, or C6 in 1,3-azaborine. This is the result of the conformational change that places the N LP in the plane of the ring and the NH bonds in a favourable spatial position to act as acceptors of π-electron density.
PB  - Royal Society of Chemistry
T2  - Physical Chemistry Chemical Physics
T1  - Does aromaticity account for an enhanced thermodynamic stability? The case of monosubstituted azaborines and the stereoelectronic chameleonism of the NH2 group
VL  - 21
IS  - 18
SP  - 9465
EP  - 9476
DO  - 10.1039/C9CP01011D
ER  - 

@article{
author = "Baranac-Stojanović, Marija and Stojanović, Milovan",
year = "2019",
abstract = "This work was initiated by the increasing interest in BN/CC isosterism and by the long-lasting interest in the concepts of aromaticity and substituent effects. We have theoretically examined the aromaticity and stability of monosubstituted BN isosters of benzene, the three isomeric azaborines. The results provide insight into the effect of substitution on two basic molecular properties, which are influenced, here, by the substituent effects and by the B/N relationship in the ring. The results, along with other examples in the literature, also warn chemists that the general belief that aromaticity accounts for enhanced thermodynamic stability is not always true. The stability of cyclic, conjugated compounds depends on several effects, and only one of them is aromaticity. In addition, our calculations predict a switching of electronic properties of the NH 2 group from the usual p-electron donor to a π-electron acceptor when it is moved from the B/C atoms to the nitrogen atom in all isomers, or C6 in 1,3-azaborine. This is the result of the conformational change that places the N LP in the plane of the ring and the NH bonds in a favourable spatial position to act as acceptors of π-electron density.",
publisher = "Royal Society of Chemistry",
journal = "Physical Chemistry Chemical Physics",
title = "Does aromaticity account for an enhanced thermodynamic stability? The case of monosubstituted azaborines and the stereoelectronic chameleonism of the NH2 group",
volume = "21",
number = "18",
pages = "9465-9476",
doi = "10.1039/C9CP01011D"
}

Baranac-Stojanović, M.,& Stojanović, M.. (2019). Does aromaticity account for an enhanced thermodynamic stability? The case of monosubstituted azaborines and the stereoelectronic chameleonism of the NH2 group. in Physical Chemistry Chemical Physics
Royal Society of Chemistry., 21(18), 9465-9476.
https://doi.org/10.1039/C9CP01011D

Baranac-Stojanović M, Stojanović M. Does aromaticity account for an enhanced thermodynamic stability? The case of monosubstituted azaborines and the stereoelectronic chameleonism of the NH2 group. in Physical Chemistry Chemical Physics. 2019;21(18):9465-9476.
doi:10.1039/C9CP01011D .

Baranac-Stojanović, Marija, Stojanović, Milovan, "Does aromaticity account for an enhanced thermodynamic stability? The case of monosubstituted azaborines and the stereoelectronic chameleonism of the NH2 group" in Physical Chemistry Chemical Physics, 21, no. 18 (2019):9465-9476,
https://doi.org/10.1039/C9CP01011D . .

TY  - JOUR
AU  - Baranac-Stojanović, Marija
AU  - Stojanović, Milovan
PY  - 2019
UR  - https://cherry.chem.bg.ac.rs/handle/123456789/3130
AB  - This work was initiated by the increasing interest in BN/CC isosterism and by the long-lasting interest in the concepts of aromaticity and substituent effects. We have theoretically examined the aromaticity and stability of monosubstituted BN isosters of benzene, the three isomeric azaborines. The results provide insight into the effect of substitution on two basic molecular properties, which are influenced, here, by the substituent effects and by the B/N relationship in the ring. The results, along with other examples in the literature, also warn chemists that the general belief that aromaticity accounts for enhanced thermodynamic stability is not always true. The stability of cyclic, conjugated compounds depends on several effects, and only one of them is aromaticity. In addition, our calculations predict a switching of electronic properties of the NH 2 group from the usual p-electron donor to a π-electron acceptor when it is moved from the B/C atoms to the nitrogen atom in all isomers, or C6 in 1,3-azaborine. This is the result of the conformational change that places the N LP in the plane of the ring and the NH bonds in a favourable spatial position to act as acceptors of π-electron density.
PB  - Royal Society of Chemistry
T2  - Physical Chemistry Chemical Physics
T1  - Does aromaticity account for an enhanced thermodynamic stability? The case of monosubstituted azaborines and the stereoelectronic chameleonism of the NH2 group
VL  - 21
IS  - 18
SP  - 9465
EP  - 9476
DO  - 10.1039/C9CP01011D
ER  - 

@article{
author = "Baranac-Stojanović, Marija and Stojanović, Milovan",
year = "2019",
abstract = "This work was initiated by the increasing interest in BN/CC isosterism and by the long-lasting interest in the concepts of aromaticity and substituent effects. We have theoretically examined the aromaticity and stability of monosubstituted BN isosters of benzene, the three isomeric azaborines. The results provide insight into the effect of substitution on two basic molecular properties, which are influenced, here, by the substituent effects and by the B/N relationship in the ring. The results, along with other examples in the literature, also warn chemists that the general belief that aromaticity accounts for enhanced thermodynamic stability is not always true. The stability of cyclic, conjugated compounds depends on several effects, and only one of them is aromaticity. In addition, our calculations predict a switching of electronic properties of the NH 2 group from the usual p-electron donor to a π-electron acceptor when it is moved from the B/C atoms to the nitrogen atom in all isomers, or C6 in 1,3-azaborine. This is the result of the conformational change that places the N LP in the plane of the ring and the NH bonds in a favourable spatial position to act as acceptors of π-electron density.",
publisher = "Royal Society of Chemistry",
journal = "Physical Chemistry Chemical Physics",
title = "Does aromaticity account for an enhanced thermodynamic stability? The case of monosubstituted azaborines and the stereoelectronic chameleonism of the NH2 group",
volume = "21",
number = "18",
pages = "9465-9476",
doi = "10.1039/C9CP01011D"
}

Baranac-Stojanović, M.,& Stojanović, M.. (2019). Does aromaticity account for an enhanced thermodynamic stability? The case of monosubstituted azaborines and the stereoelectronic chameleonism of the NH2 group. in Physical Chemistry Chemical Physics
Royal Society of Chemistry., 21(18), 9465-9476.
https://doi.org/10.1039/C9CP01011D

Baranac-Stojanović M, Stojanović M. Does aromaticity account for an enhanced thermodynamic stability? The case of monosubstituted azaborines and the stereoelectronic chameleonism of the NH2 group. in Physical Chemistry Chemical Physics. 2019;21(18):9465-9476.
doi:10.1039/C9CP01011D .

Baranac-Stojanović, Marija, Stojanović, Milovan, "Does aromaticity account for an enhanced thermodynamic stability? The case of monosubstituted azaborines and the stereoelectronic chameleonism of the NH2 group" in Physical Chemistry Chemical Physics, 21, no. 18 (2019):9465-9476,
https://doi.org/10.1039/C9CP01011D . .

TY  - DATA
AU  - Baranac-Stojanović, Marija
AU  - Stojanović, Milovan
PY  - 2019
UR  - https://cherry.chem.bg.ac.rs/handle/123456789/3131
PB  - Royal Society of Chemistry
T2  - Physical Chemistry Chemical Physics
T1  - Supplementary data for article: Baranac-Stojanović, M.; Stojanović, M. Does Aromaticity Account for an Enhanced Thermodynamic Stability? The Case of Monosubstituted Azaborines and the Stereoelectronic Chameleonism of the NH2 Group. Physical Chemistry Chemical Physics 2019, 21 (18), 9465–9476. https://doi.org/10.1039/c9cp01011d
UR  - https://hdl.handle.net/21.15107/rcub_cherry_3131
ER  - 

@misc{
author = "Baranac-Stojanović, Marija and Stojanović, Milovan",
year = "2019",
publisher = "Royal Society of Chemistry",
journal = "Physical Chemistry Chemical Physics",
title = "Supplementary data for article: Baranac-Stojanović, M.; Stojanović, M. Does Aromaticity Account for an Enhanced Thermodynamic Stability? The Case of Monosubstituted Azaborines and the Stereoelectronic Chameleonism of the NH2 Group. Physical Chemistry Chemical Physics 2019, 21 (18), 9465–9476. https://doi.org/10.1039/c9cp01011d",
url = "https://hdl.handle.net/21.15107/rcub_cherry_3131"
}

Baranac-Stojanović, M.,& Stojanović, M.. (2019). Supplementary data for article: Baranac-Stojanović, M.; Stojanović, M. Does Aromaticity Account for an Enhanced Thermodynamic Stability? The Case of Monosubstituted Azaborines and the Stereoelectronic Chameleonism of the NH2 Group. Physical Chemistry Chemical Physics 2019, 21 (18), 9465–9476. https://doi.org/10.1039/c9cp01011d. in Physical Chemistry Chemical Physics
Royal Society of Chemistry..
https://hdl.handle.net/21.15107/rcub_cherry_3131

Baranac-Stojanović M, Stojanović M. Supplementary data for article: Baranac-Stojanović, M.; Stojanović, M. Does Aromaticity Account for an Enhanced Thermodynamic Stability? The Case of Monosubstituted Azaborines and the Stereoelectronic Chameleonism of the NH2 Group. Physical Chemistry Chemical Physics 2019, 21 (18), 9465–9476. https://doi.org/10.1039/c9cp01011d. in Physical Chemistry Chemical Physics. 2019;.
https://hdl.handle.net/21.15107/rcub_cherry_3131 .

Baranac-Stojanović, Marija, Stojanović, Milovan, "Supplementary data for article: Baranac-Stojanović, M.; Stojanović, M. Does Aromaticity Account for an Enhanced Thermodynamic Stability? The Case of Monosubstituted Azaborines and the Stereoelectronic Chameleonism of the NH2 Group. Physical Chemistry Chemical Physics 2019, 21 (18), 9465–9476. https://doi.org/10.1039/c9cp01011d" in Physical Chemistry Chemical Physics (2019),
https://hdl.handle.net/21.15107/rcub_cherry_3131 .

TY  - DATA
AU  - Baranac-Stojanović, Marija
PY  - 2019
UR  - https://cherry.chem.bg.ac.rs/handle/123456789/3291
PB  - Wiley
T2  - Chemistry - A European Journal
T1  - Supplementary material for the article: Baranac-Stojanović, M. A DFT Study of the Modulation of the Antiaromatic and Open-Shell  Character of Dibenzo[a,f]Pentalene by Employing Three Strategies: Additional  Benzoannulation, BN/CC Isosterism, and Substitution. Chemistry - A European Journal  2019, 25 (41), 9747–9757. https://doi.org/10.1002/chem.201901845
UR  - https://hdl.handle.net/21.15107/rcub_cherry_3291
ER  - 

@misc{
author = "Baranac-Stojanović, Marija",
year = "2019",
publisher = "Wiley",
journal = "Chemistry - A European Journal",
title = "Supplementary material for the article: Baranac-Stojanović, M. A DFT Study of the Modulation of the Antiaromatic and Open-Shell  Character of Dibenzo[a,f]Pentalene by Employing Three Strategies: Additional  Benzoannulation, BN/CC Isosterism, and Substitution. Chemistry - A European Journal  2019, 25 (41), 9747–9757. https://doi.org/10.1002/chem.201901845",
url = "https://hdl.handle.net/21.15107/rcub_cherry_3291"
}

Baranac-Stojanović, M.. (2019). Supplementary material for the article: Baranac-Stojanović, M. A DFT Study of the Modulation of the Antiaromatic and Open-Shell  Character of Dibenzo[a,f]Pentalene by Employing Three Strategies: Additional  Benzoannulation, BN/CC Isosterism, and Substitution. Chemistry - A European Journal  2019, 25 (41), 9747–9757. https://doi.org/10.1002/chem.201901845. in Chemistry - A European Journal
Wiley..
https://hdl.handle.net/21.15107/rcub_cherry_3291

Baranac-Stojanović M. Supplementary material for the article: Baranac-Stojanović, M. A DFT Study of the Modulation of the Antiaromatic and Open-Shell  Character of Dibenzo[a,f]Pentalene by Employing Three Strategies: Additional  Benzoannulation, BN/CC Isosterism, and Substitution. Chemistry - A European Journal  2019, 25 (41), 9747–9757. https://doi.org/10.1002/chem.201901845. in Chemistry - A European Journal. 2019;.
https://hdl.handle.net/21.15107/rcub_cherry_3291 .

Baranac-Stojanović, Marija, "Supplementary material for the article: Baranac-Stojanović, M. A DFT Study of the Modulation of the Antiaromatic and Open-Shell  Character of Dibenzo[a,f]Pentalene by Employing Three Strategies: Additional  Benzoannulation, BN/CC Isosterism, and Substitution. Chemistry - A European Journal  2019, 25 (41), 9747–9757. https://doi.org/10.1002/chem.201901845" in Chemistry - A European Journal (2019),
https://hdl.handle.net/21.15107/rcub_cherry_3291 .

TY  - JOUR
AU  - Baranac-Stojanović, Marija
PY  - 2019
UR  - https://cherry.chem.bg.ac.rs/handle/123456789/3669
AB  - It is well known that benzene is aromatic in the ground state (the Hückel's rule) and antiaromatic in the first triplet (T1) excited state (the Baird's rule). Whereas its BN analogues, the three isomeric dihydro-azaborines, have been shown to have various degrees of aromaticity in their ground state, almost no data are available for their T1 states. Thus, the purpose of this work is to theoretically [B3LYP/6-311+G(d,p)] predict structures, energies, and antiaromaticity of T1 dihydro-azaborines and some benzo-fused derivatives. Conclusions are based on spin density analysis, isogyric and hydrogenation reactions, HOMA, NICS, and ACID calculations. The results suggest that singlet-triplet energy gaps, antiaromaticity, and related excited-state properties of benzene, naphthalene, and anthracene could be tuned and controlled by the BN substitution pattern. While all studied compounds remain (nearly) planar upon excitation, the spin density distribution in T1 1,4-dihydro-azaborine induces a conformational change by which the two co-planar C-H bonds in the ground state become perpendicular to each other in the excited state. This predicted change in geometry could be of interest for the design of new photomechanical materials. Excitation of B-CN/N-NH2 1,4-azaborine would have a few effects: Intramolecular charge transfer, aromaticity reversal, rotation, and stereoelectronic Umpolung of the amino group.
PB  - American Chemical Society
T2  - Journal of Organic Chemistry
T1  - Triplet-State Structures, Energies, and Antiaromaticity of BN Analogues of Benzene and Their Benzo-Fused Derivatives
VL  - 84
IS  - 21
SP  - 13582
EP  - 13594
DO  - 10.1021/acs.joc.9b01858
ER  - 

@article{
author = "Baranac-Stojanović, Marija",
year = "2019",
abstract = "It is well known that benzene is aromatic in the ground state (the Hückel's rule) and antiaromatic in the first triplet (T1) excited state (the Baird's rule). Whereas its BN analogues, the three isomeric dihydro-azaborines, have been shown to have various degrees of aromaticity in their ground state, almost no data are available for their T1 states. Thus, the purpose of this work is to theoretically [B3LYP/6-311+G(d,p)] predict structures, energies, and antiaromaticity of T1 dihydro-azaborines and some benzo-fused derivatives. Conclusions are based on spin density analysis, isogyric and hydrogenation reactions, HOMA, NICS, and ACID calculations. The results suggest that singlet-triplet energy gaps, antiaromaticity, and related excited-state properties of benzene, naphthalene, and anthracene could be tuned and controlled by the BN substitution pattern. While all studied compounds remain (nearly) planar upon excitation, the spin density distribution in T1 1,4-dihydro-azaborine induces a conformational change by which the two co-planar C-H bonds in the ground state become perpendicular to each other in the excited state. This predicted change in geometry could be of interest for the design of new photomechanical materials. Excitation of B-CN/N-NH2 1,4-azaborine would have a few effects: Intramolecular charge transfer, aromaticity reversal, rotation, and stereoelectronic Umpolung of the amino group.",
publisher = "American Chemical Society",
journal = "Journal of Organic Chemistry",
title = "Triplet-State Structures, Energies, and Antiaromaticity of BN Analogues of Benzene and Their Benzo-Fused Derivatives",
volume = "84",
number = "21",
pages = "13582-13594",
doi = "10.1021/acs.joc.9b01858"
}

Baranac-Stojanović, M.. (2019). Triplet-State Structures, Energies, and Antiaromaticity of BN Analogues of Benzene and Their Benzo-Fused Derivatives. in Journal of Organic Chemistry
American Chemical Society., 84(21), 13582-13594.
https://doi.org/10.1021/acs.joc.9b01858

Baranac-Stojanović M. Triplet-State Structures, Energies, and Antiaromaticity of BN Analogues of Benzene and Their Benzo-Fused Derivatives. in Journal of Organic Chemistry. 2019;84(21):13582-13594.
doi:10.1021/acs.joc.9b01858 .

Baranac-Stojanović, Marija, "Triplet-State Structures, Energies, and Antiaromaticity of BN Analogues of Benzene and Their Benzo-Fused Derivatives" in Journal of Organic Chemistry, 84, no. 21 (2019):13582-13594,
https://doi.org/10.1021/acs.joc.9b01858 . .

TY  - JOUR
AU  - Baranac-Stojanović, Marija
PY  - 2019
UR  - https://cherry.chem.bg.ac.rs/handle/123456789/3826
AB  - Dibenzo[a,f]pentalene ([a,f]DBP) is a highly antiaromatic molecule having appreciable open-shell singlet character in its ground state. In this work, DFT calculations at the B3LYP/6-311+G(d,p) level of theory were performed to explore the efficiency of three strategies, that is, BN/CC isosterism, substitution, and (di)benzoannulation of [a,f]DBP, in controlling its electronic state and (anti)aromaticity. To evaluate the type and extent of the latter, the harmonic oscillator model of aromaticity (HOMA) and aromatic fluctuation (FLU) indices were used, along with the nucleus-independent chemical shift NICS-XY-scan procedure. The results suggest that all three strategies could be employed to produce either the closed-shell system or open-shell species, which may be in the singlet or triplet ground state. Triplet states have been characterized as aromatic, which is in accordance with Baird's rule. All the singlet states were found to have weaker global paratropicity than [a,f]DBP. Additional (di)benzo fusion adds local aromatic subunit(s) and mainly retains the topology of the paratropic ring currents of the basic molecule. The substitution of two carbon atoms by the isoelectronic BN pair, or the introduction of substituents, results either in the same type and very similar topology of ring currents as in the parent compound, or leads to (anti)aromatic and nonaromatic subunits. The triplet states of all the examined compounds are also discussed.
PB  - Wiley
T2  - Chemistry - A European Journal
T1  - A DFT Study of the Modulation of the Antiaromatic and Open-Shell Character of Dibenzo[a,f]pentalene by Employing Three Strategies: Additional Benzoannulation, BN/CC Isosterism, and Substitution
VL  - 25
IS  - 41
SP  - 9747
EP  - 9757
DO  - 10.1002/chem.201901845
ER  - 

@article{
author = "Baranac-Stojanović, Marija",
year = "2019",
abstract = "Dibenzo[a,f]pentalene ([a,f]DBP) is a highly antiaromatic molecule having appreciable open-shell singlet character in its ground state. In this work, DFT calculations at the B3LYP/6-311+G(d,p) level of theory were performed to explore the efficiency of three strategies, that is, BN/CC isosterism, substitution, and (di)benzoannulation of [a,f]DBP, in controlling its electronic state and (anti)aromaticity. To evaluate the type and extent of the latter, the harmonic oscillator model of aromaticity (HOMA) and aromatic fluctuation (FLU) indices were used, along with the nucleus-independent chemical shift NICS-XY-scan procedure. The results suggest that all three strategies could be employed to produce either the closed-shell system or open-shell species, which may be in the singlet or triplet ground state. Triplet states have been characterized as aromatic, which is in accordance with Baird's rule. All the singlet states were found to have weaker global paratropicity than [a,f]DBP. Additional (di)benzo fusion adds local aromatic subunit(s) and mainly retains the topology of the paratropic ring currents of the basic molecule. The substitution of two carbon atoms by the isoelectronic BN pair, or the introduction of substituents, results either in the same type and very similar topology of ring currents as in the parent compound, or leads to (anti)aromatic and nonaromatic subunits. The triplet states of all the examined compounds are also discussed.",
publisher = "Wiley",
journal = "Chemistry - A European Journal",
title = "A DFT Study of the Modulation of the Antiaromatic and Open-Shell Character of Dibenzo[a,f]pentalene by Employing Three Strategies: Additional Benzoannulation, BN/CC Isosterism, and Substitution",
volume = "25",
number = "41",
pages = "9747-9757",
doi = "10.1002/chem.201901845"
}

Baranac-Stojanović, M.. (2019). A DFT Study of the Modulation of the Antiaromatic and Open-Shell Character of Dibenzo[a,f]pentalene by Employing Three Strategies: Additional Benzoannulation, BN/CC Isosterism, and Substitution. in Chemistry - A European Journal
Wiley., 25(41), 9747-9757.
https://doi.org/10.1002/chem.201901845

Baranac-Stojanović M. A DFT Study of the Modulation of the Antiaromatic and Open-Shell Character of Dibenzo[a,f]pentalene by Employing Three Strategies: Additional Benzoannulation, BN/CC Isosterism, and Substitution. in Chemistry - A European Journal. 2019;25(41):9747-9757.
doi:10.1002/chem.201901845 .

Baranac-Stojanović, Marija, "A DFT Study of the Modulation of the Antiaromatic and Open-Shell Character of Dibenzo[a,f]pentalene by Employing Three Strategies: Additional Benzoannulation, BN/CC Isosterism, and Substitution" in Chemistry - A European Journal, 25, no. 41 (2019):9747-9757,
https://doi.org/10.1002/chem.201901845 . .

TY  - JOUR
AU  - Aleksić, Jovana
AU  - Stojanović, Milovan
AU  - Baranac-Stojanović, Marija
PY  - 2018
UR  - https://cherry.chem.bg.ac.rs/handle/123456789/2188
AB  - We present an efficient, simple, metal- and solvent-free silica-gel-promoted synthesis of functionalized conjugated dienes by sequential aza-Michael/Michael reactions by starting from commercially available primary amines and propiolic esters. The scope and usefulness of the method is demonstrated for 31examples, including a range of propiolic esters, aliphatic amines, and differently substituted aromatic amines. For aliphatic amines, the products were obtained within 0.5 to 4h in 52 to 85% yield, compared with 3.5 to 22h under classical solution-phase synthesis, which proceeds with similar or lower yields. The method was found to be particularly useful for weakly nucleophilic aromatic amines, which provided products in 21 to 73% yield over 2.5 to 9.5h compared with yields of 0 to 49% over 1 to 6d under standard solution-phase conditions, and for more hydrophobic esters that gave products in yields of 47 to 79% over 1 to 3h compared with 0 to 45% over 4 to 114h in solvent.
PB  - Wiley-V C H Verlag Gmbh, Weinheim
T2  - Chemistry. An Asian Journal
T1  - Silica Gel as a Promoter of Sequential Aza-Michael/Michael Reactions of Amines and Propiolic Esters: Solvent- and Metal-Free Synthesis of Polyfunctionalized Conjugated Dienes
VL  - 13
IS  - 14
SP  - 1811
EP  - 1835
DO  - 10.1002/asia.201800645
ER  - 

@article{
author = "Aleksić, Jovana and Stojanović, Milovan and Baranac-Stojanović, Marija",
year = "2018",
abstract = "We present an efficient, simple, metal- and solvent-free silica-gel-promoted synthesis of functionalized conjugated dienes by sequential aza-Michael/Michael reactions by starting from commercially available primary amines and propiolic esters. The scope and usefulness of the method is demonstrated for 31examples, including a range of propiolic esters, aliphatic amines, and differently substituted aromatic amines. For aliphatic amines, the products were obtained within 0.5 to 4h in 52 to 85% yield, compared with 3.5 to 22h under classical solution-phase synthesis, which proceeds with similar or lower yields. The method was found to be particularly useful for weakly nucleophilic aromatic amines, which provided products in 21 to 73% yield over 2.5 to 9.5h compared with yields of 0 to 49% over 1 to 6d under standard solution-phase conditions, and for more hydrophobic esters that gave products in yields of 47 to 79% over 1 to 3h compared with 0 to 45% over 4 to 114h in solvent.",
publisher = "Wiley-V C H Verlag Gmbh, Weinheim",
journal = "Chemistry. An Asian Journal",
title = "Silica Gel as a Promoter of Sequential Aza-Michael/Michael Reactions of Amines and Propiolic Esters: Solvent- and Metal-Free Synthesis of Polyfunctionalized Conjugated Dienes",
volume = "13",
number = "14",
pages = "1811-1835",
doi = "10.1002/asia.201800645"
}

Aleksić, J., Stojanović, M.,& Baranac-Stojanović, M.. (2018). Silica Gel as a Promoter of Sequential Aza-Michael/Michael Reactions of Amines and Propiolic Esters: Solvent- and Metal-Free Synthesis of Polyfunctionalized Conjugated Dienes. in Chemistry. An Asian Journal
Wiley-V C H Verlag Gmbh, Weinheim., 13(14), 1811-1835.
https://doi.org/10.1002/asia.201800645

Aleksić J, Stojanović M, Baranac-Stojanović M. Silica Gel as a Promoter of Sequential Aza-Michael/Michael Reactions of Amines and Propiolic Esters: Solvent- and Metal-Free Synthesis of Polyfunctionalized Conjugated Dienes. in Chemistry. An Asian Journal. 2018;13(14):1811-1835.
doi:10.1002/asia.201800645 .

Aleksić, Jovana, Stojanović, Milovan, Baranac-Stojanović, Marija, "Silica Gel as a Promoter of Sequential Aza-Michael/Michael Reactions of Amines and Propiolic Esters: Solvent- and Metal-Free Synthesis of Polyfunctionalized Conjugated Dienes" in Chemistry. An Asian Journal, 13, no. 14 (2018):1811-1835,
https://doi.org/10.1002/asia.201800645 . .

TY  - JOUR
AU  - Stojanović, Milovan
AU  - Baranac-Stojanović, Marija
PY  - 2018
UR  - https://cherry.chem.bg.ac.rs/handle/123456789/2227
AB  - All isomeric BN isosteres of naphthalene have been studied theoretically, at the B3LYP/6-311+G(d,p) level, in order to investigate the effect of the BN position in a molecule on relative stability, aromaticity and frontier orbital energies. The results show that the orientational isomers of m,n/n,m type have similar aromaticity, similar HOMO-LUMO gaps and similar stability, though the latter only when both heteroatoms occupy external ring positions. This latter finding is explained by an analysis of partial atomic charges in the parent hydrocarbon and final BN-compound. Racing the BN pair in one ring results in larger stability and larger HOMO-LUMO gaps than when it is placed in separate rings. The stability order of the former series is predictable on the basis of charge distribution in the nitrogen-polarized naphthalenic system and is related to partial atomic charges at the boron and nitrogen atoms in a BN-heterocycle. The HOMO-LUMO gap of the parental hydrocarbon is retained only in the 1,4-isomer, it is slightly increased in 1,2/2,1 and 5,10 isomers and more or less decreased in all other isomers. The aromaticity of a benzene unit in naphthalene is retained/increased only in a carbocycle, when it can be represented as having a pi-electronic sextet. The aromaticity of heterocyclic rings is more or less reduced relative to naphthalene and is the weakest in the rings featuring the push-pull pi-electronic structure while the BN pair resides at the external ring positions.
PB  - Royal Soc Chemistry, Cambridge
T2  - New Journal of Chemistry
T1  - Mono BN-substituted analogues of naphthalene: a theoretical analysis of the effect of BN position on stability, aromaticity and frontier orbital energies
VL  - 42
IS  - 15
SP  - 12968
EP  - 12976
DO  - 10.1039/c8nj01529e
ER  - 

@article{
author = "Stojanović, Milovan and Baranac-Stojanović, Marija",
year = "2018",
abstract = "All isomeric BN isosteres of naphthalene have been studied theoretically, at the B3LYP/6-311+G(d,p) level, in order to investigate the effect of the BN position in a molecule on relative stability, aromaticity and frontier orbital energies. The results show that the orientational isomers of m,n/n,m type have similar aromaticity, similar HOMO-LUMO gaps and similar stability, though the latter only when both heteroatoms occupy external ring positions. This latter finding is explained by an analysis of partial atomic charges in the parent hydrocarbon and final BN-compound. Racing the BN pair in one ring results in larger stability and larger HOMO-LUMO gaps than when it is placed in separate rings. The stability order of the former series is predictable on the basis of charge distribution in the nitrogen-polarized naphthalenic system and is related to partial atomic charges at the boron and nitrogen atoms in a BN-heterocycle. The HOMO-LUMO gap of the parental hydrocarbon is retained only in the 1,4-isomer, it is slightly increased in 1,2/2,1 and 5,10 isomers and more or less decreased in all other isomers. The aromaticity of a benzene unit in naphthalene is retained/increased only in a carbocycle, when it can be represented as having a pi-electronic sextet. The aromaticity of heterocyclic rings is more or less reduced relative to naphthalene and is the weakest in the rings featuring the push-pull pi-electronic structure while the BN pair resides at the external ring positions.",
publisher = "Royal Soc Chemistry, Cambridge",
journal = "New Journal of Chemistry",
title = "Mono BN-substituted analogues of naphthalene: a theoretical analysis of the effect of BN position on stability, aromaticity and frontier orbital energies",
volume = "42",
number = "15",
pages = "12968-12976",
doi = "10.1039/c8nj01529e"
}

Stojanović, M.,& Baranac-Stojanović, M.. (2018). Mono BN-substituted analogues of naphthalene: a theoretical analysis of the effect of BN position on stability, aromaticity and frontier orbital energies. in New Journal of Chemistry
Royal Soc Chemistry, Cambridge., 42(15), 12968-12976.
https://doi.org/10.1039/c8nj01529e

Stojanović M, Baranac-Stojanović M. Mono BN-substituted analogues of naphthalene: a theoretical analysis of the effect of BN position on stability, aromaticity and frontier orbital energies. in New Journal of Chemistry. 2018;42(15):12968-12976.
doi:10.1039/c8nj01529e .

Stojanović, Milovan, Baranac-Stojanović, Marija, "Mono BN-substituted analogues of naphthalene: a theoretical analysis of the effect of BN position on stability, aromaticity and frontier orbital energies" in New Journal of Chemistry, 42, no. 15 (2018):12968-12976,
https://doi.org/10.1039/c8nj01529e . .

TY  - JOUR
AU  - Aleksić, Jovana
AU  - Stojanović, Milovan
AU  - Baranac-Stojanović, Marija
PY  - 2018
UR  - https://cherry.chem.bg.ac.rs/handle/123456789/2947
AB  - We present an efficient, simple, metal- and solvent-free silica-gel-promoted synthesis of functionalized conjugated dienes by sequential aza-Michael/Michael reactions by starting from commercially available primary amines and propiolic esters. The scope and usefulness of the method is demonstrated for 31examples, including a range of propiolic esters, aliphatic amines, and differently substituted aromatic amines. For aliphatic amines, the products were obtained within 0.5 to 4h in 52 to 85% yield, compared with 3.5 to 22h under classical solution-phase synthesis, which proceeds with similar or lower yields. The method was found to be particularly useful for weakly nucleophilic aromatic amines, which provided products in 21 to 73% yield over 2.5 to 9.5h compared with yields of 0 to 49% over 1 to 6d under standard solution-phase conditions, and for more hydrophobic esters that gave products in yields of 47 to 79% over 1 to 3h compared with 0 to 45% over 4 to 114h in solvent.
PB  - Wiley-V C H Verlag Gmbh, Weinheim
T2  - Chemistry. An Asian Journal
T1  - Silica Gel as a Promoter of Sequential Aza-Michael/Michael Reactions of Amines and Propiolic Esters: Solvent- and Metal-Free Synthesis of Polyfunctionalized Conjugated Dienes
VL  - 13
IS  - 14
SP  - 1811
EP  - 1835
DO  - 10.1002/asia.201800645
ER  - 

@article{
author = "Aleksić, Jovana and Stojanović, Milovan and Baranac-Stojanović, Marija",
year = "2018",
abstract = "We present an efficient, simple, metal- and solvent-free silica-gel-promoted synthesis of functionalized conjugated dienes by sequential aza-Michael/Michael reactions by starting from commercially available primary amines and propiolic esters. The scope and usefulness of the method is demonstrated for 31examples, including a range of propiolic esters, aliphatic amines, and differently substituted aromatic amines. For aliphatic amines, the products were obtained within 0.5 to 4h in 52 to 85% yield, compared with 3.5 to 22h under classical solution-phase synthesis, which proceeds with similar or lower yields. The method was found to be particularly useful for weakly nucleophilic aromatic amines, which provided products in 21 to 73% yield over 2.5 to 9.5h compared with yields of 0 to 49% over 1 to 6d under standard solution-phase conditions, and for more hydrophobic esters that gave products in yields of 47 to 79% over 1 to 3h compared with 0 to 45% over 4 to 114h in solvent.",
publisher = "Wiley-V C H Verlag Gmbh, Weinheim",
journal = "Chemistry. An Asian Journal",
title = "Silica Gel as a Promoter of Sequential Aza-Michael/Michael Reactions of Amines and Propiolic Esters: Solvent- and Metal-Free Synthesis of Polyfunctionalized Conjugated Dienes",
volume = "13",
number = "14",
pages = "1811-1835",
doi = "10.1002/asia.201800645"
}

Aleksić, J., Stojanović, M.,& Baranac-Stojanović, M.. (2018). Silica Gel as a Promoter of Sequential Aza-Michael/Michael Reactions of Amines and Propiolic Esters: Solvent- and Metal-Free Synthesis of Polyfunctionalized Conjugated Dienes. in Chemistry. An Asian Journal
Wiley-V C H Verlag Gmbh, Weinheim., 13(14), 1811-1835.
https://doi.org/10.1002/asia.201800645

Aleksić J, Stojanović M, Baranac-Stojanović M. Silica Gel as a Promoter of Sequential Aza-Michael/Michael Reactions of Amines and Propiolic Esters: Solvent- and Metal-Free Synthesis of Polyfunctionalized Conjugated Dienes. in Chemistry. An Asian Journal. 2018;13(14):1811-1835.
doi:10.1002/asia.201800645 .

Aleksić, Jovana, Stojanović, Milovan, Baranac-Stojanović, Marija, "Silica Gel as a Promoter of Sequential Aza-Michael/Michael Reactions of Amines and Propiolic Esters: Solvent- and Metal-Free Synthesis of Polyfunctionalized Conjugated Dienes" in Chemistry. An Asian Journal, 13, no. 14 (2018):1811-1835,
https://doi.org/10.1002/asia.201800645 . .

TY  - JOUR
AU  - Stojanović, Milovan
AU  - Baranac-Stojanović, Marija
PY  - 2018
UR  - https://cherry.chem.bg.ac.rs/handle/123456789/3240
AB  - All isomeric BN isosteres of naphthalene have been studied theoretically, at the B3LYP/6-311+G(d,p) level, in order to investigate the effect of the BN position in a molecule on relative stability, aromaticity and frontier orbital energies. The results show that the orientational isomers of m,n/n,m type have similar aromaticity, similar HOMO-LUMO gaps and similar stability, though the latter only when both heteroatoms occupy external ring positions. This latter finding is explained by an analysis of partial atomic charges in the parent hydrocarbon and final BN-compound. Racing the BN pair in one ring results in larger stability and larger HOMO-LUMO gaps than when it is placed in separate rings. The stability order of the former series is predictable on the basis of charge distribution in the nitrogen-polarized naphthalenic system and is related to partial atomic charges at the boron and nitrogen atoms in a BN-heterocycle. The HOMO-LUMO gap of the parental hydrocarbon is retained only in the 1,4-isomer, it is slightly increased in 1,2/2,1 and 5,10 isomers and more or less decreased in all other isomers. The aromaticity of a benzene unit in naphthalene is retained/increased only in a carbocycle, when it can be represented as having a pi-electronic sextet. The aromaticity of heterocyclic rings is more or less reduced relative to naphthalene and is the weakest in the rings featuring the push-pull pi-electronic structure while the BN pair resides at the external ring positions.
PB  - Royal Soc Chemistry, Cambridge
T2  - New Journal of Chemistry
T1  - Mono BN-substituted analogues of naphthalene: a theoretical analysis of the effect of BN position on stability, aromaticity and frontier orbital energies
VL  - 42
IS  - 15
SP  - 12968
EP  - 12976
DO  - 10.1039/c8nj01529e
ER  - 

@article{
author = "Stojanović, Milovan and Baranac-Stojanović, Marija",
year = "2018",
abstract = "All isomeric BN isosteres of naphthalene have been studied theoretically, at the B3LYP/6-311+G(d,p) level, in order to investigate the effect of the BN position in a molecule on relative stability, aromaticity and frontier orbital energies. The results show that the orientational isomers of m,n/n,m type have similar aromaticity, similar HOMO-LUMO gaps and similar stability, though the latter only when both heteroatoms occupy external ring positions. This latter finding is explained by an analysis of partial atomic charges in the parent hydrocarbon and final BN-compound. Racing the BN pair in one ring results in larger stability and larger HOMO-LUMO gaps than when it is placed in separate rings. The stability order of the former series is predictable on the basis of charge distribution in the nitrogen-polarized naphthalenic system and is related to partial atomic charges at the boron and nitrogen atoms in a BN-heterocycle. The HOMO-LUMO gap of the parental hydrocarbon is retained only in the 1,4-isomer, it is slightly increased in 1,2/2,1 and 5,10 isomers and more or less decreased in all other isomers. The aromaticity of a benzene unit in naphthalene is retained/increased only in a carbocycle, when it can be represented as having a pi-electronic sextet. The aromaticity of heterocyclic rings is more or less reduced relative to naphthalene and is the weakest in the rings featuring the push-pull pi-electronic structure while the BN pair resides at the external ring positions.",
publisher = "Royal Soc Chemistry, Cambridge",
journal = "New Journal of Chemistry",
title = "Mono BN-substituted analogues of naphthalene: a theoretical analysis of the effect of BN position on stability, aromaticity and frontier orbital energies",
volume = "42",
number = "15",
pages = "12968-12976",
doi = "10.1039/c8nj01529e"
}

Stojanović, M.,& Baranac-Stojanović, M.. (2018). Mono BN-substituted analogues of naphthalene: a theoretical analysis of the effect of BN position on stability, aromaticity and frontier orbital energies. in New Journal of Chemistry
Royal Soc Chemistry, Cambridge., 42(15), 12968-12976.
https://doi.org/10.1039/c8nj01529e

Stojanović M, Baranac-Stojanović M. Mono BN-substituted analogues of naphthalene: a theoretical analysis of the effect of BN position on stability, aromaticity and frontier orbital energies. in New Journal of Chemistry. 2018;42(15):12968-12976.
doi:10.1039/c8nj01529e .

Stojanović, Milovan, Baranac-Stojanović, Marija, "Mono BN-substituted analogues of naphthalene: a theoretical analysis of the effect of BN position on stability, aromaticity and frontier orbital energies" in New Journal of Chemistry, 42, no. 15 (2018):12968-12976,
https://doi.org/10.1039/c8nj01529e . .

TY  - DATA
AU  - Stojanović, Milovan
AU  - Baranac-Stojanović, Marija
PY  - 2018
UR  - https://cherry.chem.bg.ac.rs/handle/123456789/3241
PB  - Royal Soc Chemistry, Cambridge
T2  - New Journal of Chemistry
T1  - Supplementary material for the article: Stojanović, M.; Baranac-Stojanović, M. Mono BN-Substituted Analogues of Naphthalene: A Theoretical Analysis of the Effect of BN Position on Stability, Aromaticity and Frontier Orbital Energies. New Journal of Chemistry 2018, 42 (15), 12968–12976. https://doi.org/10.1039/c8nj01529e
UR  - https://hdl.handle.net/21.15107/rcub_cherry_3241
ER  - 

@misc{
author = "Stojanović, Milovan and Baranac-Stojanović, Marija",
year = "2018",
publisher = "Royal Soc Chemistry, Cambridge",
journal = "New Journal of Chemistry",
title = "Supplementary material for the article: Stojanović, M.; Baranac-Stojanović, M. Mono BN-Substituted Analogues of Naphthalene: A Theoretical Analysis of the Effect of BN Position on Stability, Aromaticity and Frontier Orbital Energies. New Journal of Chemistry 2018, 42 (15), 12968–12976. https://doi.org/10.1039/c8nj01529e",
url = "https://hdl.handle.net/21.15107/rcub_cherry_3241"
}

Stojanović, M.,& Baranac-Stojanović, M.. (2018). Supplementary material for the article: Stojanović, M.; Baranac-Stojanović, M. Mono BN-Substituted Analogues of Naphthalene: A Theoretical Analysis of the Effect of BN Position on Stability, Aromaticity and Frontier Orbital Energies. New Journal of Chemistry 2018, 42 (15), 12968–12976. https://doi.org/10.1039/c8nj01529e. in New Journal of Chemistry
Royal Soc Chemistry, Cambridge..
https://hdl.handle.net/21.15107/rcub_cherry_3241

Stojanović M, Baranac-Stojanović M. Supplementary material for the article: Stojanović, M.; Baranac-Stojanović, M. Mono BN-Substituted Analogues of Naphthalene: A Theoretical Analysis of the Effect of BN Position on Stability, Aromaticity and Frontier Orbital Energies. New Journal of Chemistry 2018, 42 (15), 12968–12976. https://doi.org/10.1039/c8nj01529e. in New Journal of Chemistry. 2018;.
https://hdl.handle.net/21.15107/rcub_cherry_3241 .

Stojanović, Milovan, Baranac-Stojanović, Marija, "Supplementary material for the article: Stojanović, M.; Baranac-Stojanović, M. Mono BN-Substituted Analogues of Naphthalene: A Theoretical Analysis of the Effect of BN Position on Stability, Aromaticity and Frontier Orbital Energies. New Journal of Chemistry 2018, 42 (15), 12968–12976. https://doi.org/10.1039/c8nj01529e" in New Journal of Chemistry (2018),
https://hdl.handle.net/21.15107/rcub_cherry_3241 .

TY  - JOUR
AU  - Baranac-Stojanović, Marija
PY  - 2018
UR  - https://cherry.chem.bg.ac.rs/handle/123456789/3180
AB  - The classical textbook explanation of variations of (HNMR)-H-1 chemical shifts in benzenes bearing an electron-donating (NH2) or an electron-withdrawing (NO2) group in terms of substituent resonance effects was examined by analyzing molecular orbital contributions to the total shielding. It was found that the -electronic system showed a more pronounced shielding effect on all ring hydrogen atoms, relative to benzene, irrespective of substituent +R/-R effects. For the latter, this was in contrast to the traditional explanations of downfield shift of nitrobenzene proton resonances, which were found to be determined by the sigma-electronic system and oxygen in-plane lone pairs. In aniline, the +R effect of NH2 group can be used to fully explain the upfield position of meta-H signals and partly the upfield position of para-H signals, the latter also being influenced by the sigma-system. The position of the lowest frequency signal of ortho-Hs was fully determined by sigma-electrons.
PB  - Wiley-V C H Verlag Gmbh, Weinheim
T2  - Chemistry. An Asian Journal
T1  - Can Variations of (HNMR)-H-1 Chemical Shifts in Benzene Substituted with an Electron-Accepting (NO2)/Donating (NH2) Group be Explained in Terms of Resonance Effects of Substituents?
VL  - 13
IS  - 7
SP  - 877
EP  - 881
DO  - 10.1002/asia.201800137
ER  - 

@article{
author = "Baranac-Stojanović, Marija",
year = "2018",
abstract = "The classical textbook explanation of variations of (HNMR)-H-1 chemical shifts in benzenes bearing an electron-donating (NH2) or an electron-withdrawing (NO2) group in terms of substituent resonance effects was examined by analyzing molecular orbital contributions to the total shielding. It was found that the -electronic system showed a more pronounced shielding effect on all ring hydrogen atoms, relative to benzene, irrespective of substituent +R/-R effects. For the latter, this was in contrast to the traditional explanations of downfield shift of nitrobenzene proton resonances, which were found to be determined by the sigma-electronic system and oxygen in-plane lone pairs. In aniline, the +R effect of NH2 group can be used to fully explain the upfield position of meta-H signals and partly the upfield position of para-H signals, the latter also being influenced by the sigma-system. The position of the lowest frequency signal of ortho-Hs was fully determined by sigma-electrons.",
publisher = "Wiley-V C H Verlag Gmbh, Weinheim",
journal = "Chemistry. An Asian Journal",
title = "Can Variations of (HNMR)-H-1 Chemical Shifts in Benzene Substituted with an Electron-Accepting (NO2)/Donating (NH2) Group be Explained in Terms of Resonance Effects of Substituents?",
volume = "13",
number = "7",
pages = "877-881",
doi = "10.1002/asia.201800137"
}

Baranac-Stojanović, M.. (2018). Can Variations of (HNMR)-H-1 Chemical Shifts in Benzene Substituted with an Electron-Accepting (NO2)/Donating (NH2) Group be Explained in Terms of Resonance Effects of Substituents?. in Chemistry. An Asian Journal
Wiley-V C H Verlag Gmbh, Weinheim., 13(7), 877-881.
https://doi.org/10.1002/asia.201800137

Baranac-Stojanović M. Can Variations of (HNMR)-H-1 Chemical Shifts in Benzene Substituted with an Electron-Accepting (NO2)/Donating (NH2) Group be Explained in Terms of Resonance Effects of Substituents?. in Chemistry. An Asian Journal. 2018;13(7):877-881.
doi:10.1002/asia.201800137 .

Baranac-Stojanović, Marija, "Can Variations of (HNMR)-H-1 Chemical Shifts in Benzene Substituted with an Electron-Accepting (NO2)/Donating (NH2) Group be Explained in Terms of Resonance Effects of Substituents?" in Chemistry. An Asian Journal, 13, no. 7 (2018):877-881,
https://doi.org/10.1002/asia.201800137 . .

TY  - DATA
AU  - Baranac-Stojanović, Marija
PY  - 2018
UR  - https://cherry.chem.bg.ac.rs/handle/123456789/3181
PB  - Wiley-V C H Verlag Gmbh, Weinheim
T2  - Chemistry. An Asian Journal
T1  - Supplementary material for the article: Baranac-Stojanović, M. Can Variations of 1H NMR Chemical Shifts in Benzene Substituted  with an Electron-Accepting (NO2)/Donating (NH2) Group Be Explained in Terms of  Resonance Effects of Substituents? Chemistry - An Asian Journal 2018, 13 (7), 877–881.  https://doi.org/10.1002/asia.201800137
UR  - https://hdl.handle.net/21.15107/rcub_cherry_3181
ER  - 

@misc{
author = "Baranac-Stojanović, Marija",
year = "2018",
publisher = "Wiley-V C H Verlag Gmbh, Weinheim",
journal = "Chemistry. An Asian Journal",
title = "Supplementary material for the article: Baranac-Stojanović, M. Can Variations of 1H NMR Chemical Shifts in Benzene Substituted  with an Electron-Accepting (NO2)/Donating (NH2) Group Be Explained in Terms of  Resonance Effects of Substituents? Chemistry - An Asian Journal 2018, 13 (7), 877–881.  https://doi.org/10.1002/asia.201800137",
url = "https://hdl.handle.net/21.15107/rcub_cherry_3181"
}

Baranac-Stojanović, M.. (2018). Supplementary material for the article: Baranac-Stojanović, M. Can Variations of 1H NMR Chemical Shifts in Benzene Substituted  with an Electron-Accepting (NO2)/Donating (NH2) Group Be Explained in Terms of  Resonance Effects of Substituents? Chemistry - An Asian Journal 2018, 13 (7), 877–881.  https://doi.org/10.1002/asia.201800137. in Chemistry. An Asian Journal
Wiley-V C H Verlag Gmbh, Weinheim..
https://hdl.handle.net/21.15107/rcub_cherry_3181

Baranac-Stojanović M. Supplementary material for the article: Baranac-Stojanović, M. Can Variations of 1H NMR Chemical Shifts in Benzene Substituted  with an Electron-Accepting (NO2)/Donating (NH2) Group Be Explained in Terms of  Resonance Effects of Substituents? Chemistry - An Asian Journal 2018, 13 (7), 877–881.  https://doi.org/10.1002/asia.201800137. in Chemistry. An Asian Journal. 2018;.
https://hdl.handle.net/21.15107/rcub_cherry_3181 .

Baranac-Stojanović, Marija, "Supplementary material for the article: Baranac-Stojanović, M. Can Variations of 1H NMR Chemical Shifts in Benzene Substituted  with an Electron-Accepting (NO2)/Donating (NH2) Group Be Explained in Terms of  Resonance Effects of Substituents? Chemistry - An Asian Journal 2018, 13 (7), 877–881.  https://doi.org/10.1002/asia.201800137" in Chemistry. An Asian Journal (2018),
https://hdl.handle.net/21.15107/rcub_cherry_3181 .

TY  - JOUR
AU  - Baranac-Stojanović, Marija
PY  - 2018
UR  - https://cherry.chem.bg.ac.rs/handle/123456789/2127
AB  - The classical textbook explanation of variations of (HNMR)-H-1 chemical shifts in benzenes bearing an electron-donating (NH2) or an electron-withdrawing (NO2) group in terms of substituent resonance effects was examined by analyzing molecular orbital contributions to the total shielding. It was found that the -electronic system showed a more pronounced shielding effect on all ring hydrogen atoms, relative to benzene, irrespective of substituent +R/-R effects. For the latter, this was in contrast to the traditional explanations of downfield shift of nitrobenzene proton resonances, which were found to be determined by the sigma-electronic system and oxygen in-plane lone pairs. In aniline, the +R effect of NH2 group can be used to fully explain the upfield position of meta-H signals and partly the upfield position of para-H signals, the latter also being influenced by the sigma-system. The position of the lowest frequency signal of ortho-Hs was fully determined by sigma-electrons.
PB  - Wiley-V C H Verlag Gmbh, Weinheim
T2  - Chemistry. An Asian Journal
T1  - Can Variations of (HNMR)-H-1 Chemical Shifts in Benzene Substituted with an Electron-Accepting (NO2)/Donating (NH2) Group be Explained in Terms of Resonance Effects of Substituents?
VL  - 13
IS  - 7
SP  - 877
EP  - 881
DO  - 10.1002/asia.201800137
ER  - 

@article{
author = "Baranac-Stojanović, Marija",
year = "2018",
abstract = "The classical textbook explanation of variations of (HNMR)-H-1 chemical shifts in benzenes bearing an electron-donating (NH2) or an electron-withdrawing (NO2) group in terms of substituent resonance effects was examined by analyzing molecular orbital contributions to the total shielding. It was found that the -electronic system showed a more pronounced shielding effect on all ring hydrogen atoms, relative to benzene, irrespective of substituent +R/-R effects. For the latter, this was in contrast to the traditional explanations of downfield shift of nitrobenzene proton resonances, which were found to be determined by the sigma-electronic system and oxygen in-plane lone pairs. In aniline, the +R effect of NH2 group can be used to fully explain the upfield position of meta-H signals and partly the upfield position of para-H signals, the latter also being influenced by the sigma-system. The position of the lowest frequency signal of ortho-Hs was fully determined by sigma-electrons.",
publisher = "Wiley-V C H Verlag Gmbh, Weinheim",
journal = "Chemistry. An Asian Journal",
title = "Can Variations of (HNMR)-H-1 Chemical Shifts in Benzene Substituted with an Electron-Accepting (NO2)/Donating (NH2) Group be Explained in Terms of Resonance Effects of Substituents?",
volume = "13",
number = "7",
pages = "877-881",
doi = "10.1002/asia.201800137"
}

Baranac-Stojanović, M.. (2018). Can Variations of (HNMR)-H-1 Chemical Shifts in Benzene Substituted with an Electron-Accepting (NO2)/Donating (NH2) Group be Explained in Terms of Resonance Effects of Substituents?. in Chemistry. An Asian Journal
Wiley-V C H Verlag Gmbh, Weinheim., 13(7), 877-881.
https://doi.org/10.1002/asia.201800137

Baranac-Stojanović M. Can Variations of (HNMR)-H-1 Chemical Shifts in Benzene Substituted with an Electron-Accepting (NO2)/Donating (NH2) Group be Explained in Terms of Resonance Effects of Substituents?. in Chemistry. An Asian Journal. 2018;13(7):877-881.
doi:10.1002/asia.201800137 .

Baranac-Stojanović, Marija, "Can Variations of (HNMR)-H-1 Chemical Shifts in Benzene Substituted with an Electron-Accepting (NO2)/Donating (NH2) Group be Explained in Terms of Resonance Effects of Substituents?" in Chemistry. An Asian Journal, 13, no. 7 (2018):877-881,
https://doi.org/10.1002/asia.201800137 . .

TY  - JOUR
AU  - Baranac-Stojanović, Marija
AU  - Stojanović, Milovan
AU  - Aleksić, Jovana
PY  - 2017
UR  - https://cherry.chem.bg.ac.rs/handle/123456789/2464
AB  - The strength of the azido gauche effect in 1,2-diazidoethane, N-(2-azidoethyl)ethanamide, (protonated) 2-azidoethanamine and (protonated) 2-azidoethanol and its origin were theoretically studied at the MP2/6-311++G(d,p) level of theory. The results show that the azido gauche effect in the amine and alcohol can exert a control over the molecular conformation to a similar extent as the fluorine gauche effect, but to a greater extent in the charged species, amide and vicinal diazido fragment. A quantitative partitioning of isomerization energy into contributions from electrostatic, orbital, dispersion and Pauli interactions and energy consumed in structural changes revealed that electrostatic forces play an important role in the stabilization of the gauche isomer in the two charged species and alcohol. Electrostatic and dispersion interactions are the main contributors to the gauche effect in the amide, whereas dispersion and orbital interactions can be considered to be the two most important stabilizing factors of the gauche form in the vicinal diazido fragment. The interplay of all three stabilizing interactions determines the gauche preference in the amine. Stereoelectronic effects, which are involved in orbital interactions, contribute to the gauche effect in all the molecules except the 2-azidoethylammonium ion and protonated 2-azidoethanol. Hydrogen-bonding interactions were found only in the protonated alcohol.
PB  - Royal Soc Chemistry, Cambridge
T2  - New Journal of Chemistry
T1  - Theoretical study of azido gauche effect and its origin
VL  - 41
IS  - 11
SP  - 4644
EP  - 4661
DO  - 10.1039/c7nj00369b
ER  - 

@article{
author = "Baranac-Stojanović, Marija and Stojanović, Milovan and Aleksić, Jovana",
year = "2017",
abstract = "The strength of the azido gauche effect in 1,2-diazidoethane, N-(2-azidoethyl)ethanamide, (protonated) 2-azidoethanamine and (protonated) 2-azidoethanol and its origin were theoretically studied at the MP2/6-311++G(d,p) level of theory. The results show that the azido gauche effect in the amine and alcohol can exert a control over the molecular conformation to a similar extent as the fluorine gauche effect, but to a greater extent in the charged species, amide and vicinal diazido fragment. A quantitative partitioning of isomerization energy into contributions from electrostatic, orbital, dispersion and Pauli interactions and energy consumed in structural changes revealed that electrostatic forces play an important role in the stabilization of the gauche isomer in the two charged species and alcohol. Electrostatic and dispersion interactions are the main contributors to the gauche effect in the amide, whereas dispersion and orbital interactions can be considered to be the two most important stabilizing factors of the gauche form in the vicinal diazido fragment. The interplay of all three stabilizing interactions determines the gauche preference in the amine. Stereoelectronic effects, which are involved in orbital interactions, contribute to the gauche effect in all the molecules except the 2-azidoethylammonium ion and protonated 2-azidoethanol. Hydrogen-bonding interactions were found only in the protonated alcohol.",
publisher = "Royal Soc Chemistry, Cambridge",
journal = "New Journal of Chemistry",
title = "Theoretical study of azido gauche effect and its origin",
volume = "41",
number = "11",
pages = "4644-4661",
doi = "10.1039/c7nj00369b"
}

Baranac-Stojanović, M., Stojanović, M.,& Aleksić, J.. (2017). Theoretical study of azido gauche effect and its origin. in New Journal of Chemistry
Royal Soc Chemistry, Cambridge., 41(11), 4644-4661.
https://doi.org/10.1039/c7nj00369b

Baranac-Stojanović M, Stojanović M, Aleksić J. Theoretical study of azido gauche effect and its origin. in New Journal of Chemistry. 2017;41(11):4644-4661.
doi:10.1039/c7nj00369b .

Baranac-Stojanović, Marija, Stojanović, Milovan, Aleksić, Jovana, "Theoretical study of azido gauche effect and its origin" in New Journal of Chemistry, 41, no. 11 (2017):4644-4661,
https://doi.org/10.1039/c7nj00369b . .

TY  - DATA
AU  - Baranac-Stojanović, Marija
AU  - Stojanović, Milovan
AU  - Aleksić, Jovana
PY  - 2017
UR  - https://cherry.chem.bg.ac.rs/handle/123456789/3260
PB  - Royal Soc Chemistry, Cambridge
T2  - New Journal of Chemistry
T1  - Supplementary material for the article: Baranac-Stojanović, M.; Stojanović, M.; Aleksić, J. Theoretical Study of Azido: Gauche Effect and Its Origin. New Journal of Chemistry 2017, 41 (11), 4644–4661. https://doi.org/10.1039/c7nj00369b
UR  - https://hdl.handle.net/21.15107/rcub_cherry_3260
ER  - 

@misc{
author = "Baranac-Stojanović, Marija and Stojanović, Milovan and Aleksić, Jovana",
year = "2017",
publisher = "Royal Soc Chemistry, Cambridge",
journal = "New Journal of Chemistry",
title = "Supplementary material for the article: Baranac-Stojanović, M.; Stojanović, M.; Aleksić, J. Theoretical Study of Azido: Gauche Effect and Its Origin. New Journal of Chemistry 2017, 41 (11), 4644–4661. https://doi.org/10.1039/c7nj00369b",
url = "https://hdl.handle.net/21.15107/rcub_cherry_3260"
}

Baranac-Stojanović, M., Stojanović, M.,& Aleksić, J.. (2017). Supplementary material for the article: Baranac-Stojanović, M.; Stojanović, M.; Aleksić, J. Theoretical Study of Azido: Gauche Effect and Its Origin. New Journal of Chemistry 2017, 41 (11), 4644–4661. https://doi.org/10.1039/c7nj00369b. in New Journal of Chemistry
Royal Soc Chemistry, Cambridge..
https://hdl.handle.net/21.15107/rcub_cherry_3260

Baranac-Stojanović M, Stojanović M, Aleksić J. Supplementary material for the article: Baranac-Stojanović, M.; Stojanović, M.; Aleksić, J. Theoretical Study of Azido: Gauche Effect and Its Origin. New Journal of Chemistry 2017, 41 (11), 4644–4661. https://doi.org/10.1039/c7nj00369b. in New Journal of Chemistry. 2017;.
https://hdl.handle.net/21.15107/rcub_cherry_3260 .

Baranac-Stojanović, Marija, Stojanović, Milovan, Aleksić, Jovana, "Supplementary material for the article: Baranac-Stojanović, M.; Stojanović, M.; Aleksić, J. Theoretical Study of Azido: Gauche Effect and Its Origin. New Journal of Chemistry 2017, 41 (11), 4644–4661. https://doi.org/10.1039/c7nj00369b" in New Journal of Chemistry (2017),
https://hdl.handle.net/21.15107/rcub_cherry_3260 .

TY  - JOUR
AU  - Baranac-Stojanović, Marija
PY  - 2017
UR  - https://cherry.chem.bg.ac.rs/handle/123456789/3825
AB  - This is a theoretical (DFT) study of the impact of electronic structural changes, induced by B-N/C-C isosterism, on two basic properties of 4-electron antiaromatic system, that is, stability and antiaromaticity. The main driving force for the nonplanarity of B2N2 rings is electrostatic energy, and that for a ring with one B-N unit is the relief of Pauli repulsion. The charge-separation instability, inherent for a 1,3-B,N relationship, turns the ground state of the BCNC system to an aromatic triplet, which is less stable than the isomeric BNCC system, mostly because of larger Pauli interactions. The alternating BNBN connectivity is favoured primarily by orbital interaction energy and, secondarily, by better electrostatic attraction. The C-C B-N substitution weakens the antiaromatic character, except that for a 1,3-B,N relationship, which results in increased antiaromaticity in the closed-shell state relative to that of cyclobutadiene.
PB  - Wiley-V C H Verlag Gmbh, Weinheim
T2  - European Journal of Organic Chemistry
T1  - 4-Electron B-N Monocycles: Stability and (Anti)aromaticity
IS  - 34
SP  - 5163
EP  - 5169
UR  - https://hdl.handle.net/21.15107/rcub_cherry_3825
ER  - 

@article{
author = "Baranac-Stojanović, Marija",
year = "2017",
abstract = "This is a theoretical (DFT) study of the impact of electronic structural changes, induced by B-N/C-C isosterism, on two basic properties of 4-electron antiaromatic system, that is, stability and antiaromaticity. The main driving force for the nonplanarity of B2N2 rings is electrostatic energy, and that for a ring with one B-N unit is the relief of Pauli repulsion. The charge-separation instability, inherent for a 1,3-B,N relationship, turns the ground state of the BCNC system to an aromatic triplet, which is less stable than the isomeric BNCC system, mostly because of larger Pauli interactions. The alternating BNBN connectivity is favoured primarily by orbital interaction energy and, secondarily, by better electrostatic attraction. The C-C B-N substitution weakens the antiaromatic character, except that for a 1,3-B,N relationship, which results in increased antiaromaticity in the closed-shell state relative to that of cyclobutadiene.",
publisher = "Wiley-V C H Verlag Gmbh, Weinheim",
journal = "European Journal of Organic Chemistry",
title = "4-Electron B-N Monocycles: Stability and (Anti)aromaticity",
number = "34",
pages = "5163-5169",
url = "https://hdl.handle.net/21.15107/rcub_cherry_3825"
}

Baranac-Stojanović, M.. (2017). 4-Electron B-N Monocycles: Stability and (Anti)aromaticity. in European Journal of Organic Chemistry
Wiley-V C H Verlag Gmbh, Weinheim.(34), 5163-5169.
https://hdl.handle.net/21.15107/rcub_cherry_3825

Baranac-Stojanović M. 4-Electron B-N Monocycles: Stability and (Anti)aromaticity. in European Journal of Organic Chemistry. 2017;(34):5163-5169.
https://hdl.handle.net/21.15107/rcub_cherry_3825 .

Baranac-Stojanović, Marija, "4-Electron B-N Monocycles: Stability and (Anti)aromaticity" in European Journal of Organic Chemistry, no. 34 (2017):5163-5169,
https://hdl.handle.net/21.15107/rcub_cherry_3825 .

TY  - DATA
AU  - Džambaski, Zdravko
AU  - Baranac-Stojanović, Marija
PY  - 2017
PB  - Wiley-V C H Verlag Gmbh, Weinheim
T2  - ChemistrySelect
T1  - Supplementary data for article:            Džambaski, Z.; Baranac-Stojanović, M. Electron Delocalization in Electron-Deficient Alkenes and Push-Pull Alkenes. ChemistrySelect 2017, 2 (1), 42–50. https://doi.org/10.1002/slct.201601661
UR  - https://hdl.handle.net/21.15107/rcub_cherry_3112
ER  - 

@misc{
author = "Džambaski, Zdravko and Baranac-Stojanović, Marija",
year = "2017",
publisher = "Wiley-V C H Verlag Gmbh, Weinheim",
journal = "ChemistrySelect",
title = "Supplementary data for article:            Džambaski, Z.; Baranac-Stojanović, M. Electron Delocalization in Electron-Deficient Alkenes and Push-Pull Alkenes. ChemistrySelect 2017, 2 (1), 42–50. https://doi.org/10.1002/slct.201601661",
url = "https://hdl.handle.net/21.15107/rcub_cherry_3112"
}

Džambaski, Z.,& Baranac-Stojanović, M.. (2017). Supplementary data for article:            Džambaski, Z.; Baranac-Stojanović, M. Electron Delocalization in Electron-Deficient Alkenes and Push-Pull Alkenes. ChemistrySelect 2017, 2 (1), 42–50. https://doi.org/10.1002/slct.201601661. in ChemistrySelect
Wiley-V C H Verlag Gmbh, Weinheim..
https://hdl.handle.net/21.15107/rcub_cherry_3112

Džambaski Z, Baranac-Stojanović M. Supplementary data for article:            Džambaski, Z.; Baranac-Stojanović, M. Electron Delocalization in Electron-Deficient Alkenes and Push-Pull Alkenes. ChemistrySelect 2017, 2 (1), 42–50. https://doi.org/10.1002/slct.201601661. in ChemistrySelect. 2017;.
https://hdl.handle.net/21.15107/rcub_cherry_3112 .

Džambaski, Zdravko, Baranac-Stojanović, Marija, "Supplementary data for article:            Džambaski, Z.; Baranac-Stojanović, M. Electron Delocalization in Electron-Deficient Alkenes and Push-Pull Alkenes. ChemistrySelect 2017, 2 (1), 42–50. https://doi.org/10.1002/slct.201601661" in ChemistrySelect (2017),
https://hdl.handle.net/21.15107/rcub_cherry_3112 .

TY  - JOUR
AU  - Baranac-Stojanović, Marija
PY  - 2017
UR  - https://cherry.chem.bg.ac.rs/handle/123456789/2526
AB  - This is a theoretical (DFT) study of the impact of electronic structural changes, induced by B-N/C-C isosterism, on two basic properties of 4-electron antiaromatic system, that is, stability and antiaromaticity. The main driving force for the nonplanarity of B2N2 rings is electrostatic energy, and that for a ring with one B-N unit is the relief of Pauli repulsion. The charge-separation instability, inherent for a 1,3-B,N relationship, turns the ground state of the BCNC system to an aromatic triplet, which is less stable than the isomeric BNCC system, mostly because of larger Pauli interactions. The alternating BNBN connectivity is favoured primarily by orbital interaction energy and, secondarily, by better electrostatic attraction. The C-C B-N substitution weakens the antiaromatic character, except that for a 1,3-B,N relationship, which results in increased antiaromaticity in the closed-shell state relative to that of cyclobutadiene.
PB  - Wiley-V C H Verlag Gmbh, Weinheim
T2  - European Journal of Organic Chemistry
T1  - 4-Electron B-N Monocycles: Stability and (Anti)aromaticity
IS  - 34
SP  - 5163
EP  - 5169
DO  - 10.1002/ejoc.201700959
ER  - 

@article{
author = "Baranac-Stojanović, Marija",
year = "2017",
abstract = "This is a theoretical (DFT) study of the impact of electronic structural changes, induced by B-N/C-C isosterism, on two basic properties of 4-electron antiaromatic system, that is, stability and antiaromaticity. The main driving force for the nonplanarity of B2N2 rings is electrostatic energy, and that for a ring with one B-N unit is the relief of Pauli repulsion. The charge-separation instability, inherent for a 1,3-B,N relationship, turns the ground state of the BCNC system to an aromatic triplet, which is less stable than the isomeric BNCC system, mostly because of larger Pauli interactions. The alternating BNBN connectivity is favoured primarily by orbital interaction energy and, secondarily, by better electrostatic attraction. The C-C B-N substitution weakens the antiaromatic character, except that for a 1,3-B,N relationship, which results in increased antiaromaticity in the closed-shell state relative to that of cyclobutadiene.",
publisher = "Wiley-V C H Verlag Gmbh, Weinheim",
journal = "European Journal of Organic Chemistry",
title = "4-Electron B-N Monocycles: Stability and (Anti)aromaticity",
number = "34",
pages = "5163-5169",
doi = "10.1002/ejoc.201700959"
}

Baranac-Stojanović, M.. (2017). 4-Electron B-N Monocycles: Stability and (Anti)aromaticity. in European Journal of Organic Chemistry
Wiley-V C H Verlag Gmbh, Weinheim.(34), 5163-5169.
https://doi.org/10.1002/ejoc.201700959

Baranac-Stojanović M. 4-Electron B-N Monocycles: Stability and (Anti)aromaticity. in European Journal of Organic Chemistry. 2017;(34):5163-5169.
doi:10.1002/ejoc.201700959 .

Baranac-Stojanović, Marija, "4-Electron B-N Monocycles: Stability and (Anti)aromaticity" in European Journal of Organic Chemistry, no. 34 (2017):5163-5169,
https://doi.org/10.1002/ejoc.201700959 . .

TY  - JOUR
AU  - Džambaski, Zdravko
AU  - Baranac-Stojanović, Marija
PY  - 2017
UR  - https://cherry.chem.bg.ac.rs/handle/123456789/2425
AB  - We have studied pi electron delocalization in electron- deficient alkenes and push- pull alkenes by means of natural bond orbital analysis at the B3LYP/6-311+ G(d,p) level. The study revealed that the rarely mentioned pi electron donation from an electron-accepting group (Acc) toward the C=C double bond in push-pull alkenes and electron-deficient alkenes can provide up to 10% of total pi electron stabilizing energy of a push-pull system and as much as 45% in a strongly electron-deficient tetracyanoethene. The Acc - gt  C= C bond pi electron donation is more intense in s-trans than in s-cis conformational arrangement, but is less dependent on Z/E isomerism in push-pull alkenes, being slightly more pronounced in Z isomers. Among different Acc substituents, CN and COO-groups contribute the largest percent of stabilizing energy and NO2 the smallest. Increase in the number of Acc groups increases percentage contribution of Acc - gt  C= C bond p electron delocalization to a system stabilization. A difference in pi*(C=C) orbital occupancy between isomers can be related with their chemical reactivity.
PB  - Wiley-V C H Verlag Gmbh, Weinheim
T2  - CHEMISTRYSELECT
T1  - Electron Delocalization in Electron-Deficient Alkenes and Push-Pull Alkenes
VL  - 2
IS  - 1
SP  - 42
EP  - 50
DO  - 10.1002/slct.201601661
ER  - 

@article{
author = "Džambaski, Zdravko and Baranac-Stojanović, Marija",
year = "2017",
abstract = "We have studied pi electron delocalization in electron- deficient alkenes and push- pull alkenes by means of natural bond orbital analysis at the B3LYP/6-311+ G(d,p) level. The study revealed that the rarely mentioned pi electron donation from an electron-accepting group (Acc) toward the C=C double bond in push-pull alkenes and electron-deficient alkenes can provide up to 10% of total pi electron stabilizing energy of a push-pull system and as much as 45% in a strongly electron-deficient tetracyanoethene. The Acc - gt  C= C bond pi electron donation is more intense in s-trans than in s-cis conformational arrangement, but is less dependent on Z/E isomerism in push-pull alkenes, being slightly more pronounced in Z isomers. Among different Acc substituents, CN and COO-groups contribute the largest percent of stabilizing energy and NO2 the smallest. Increase in the number of Acc groups increases percentage contribution of Acc - gt  C= C bond p electron delocalization to a system stabilization. A difference in pi*(C=C) orbital occupancy between isomers can be related with their chemical reactivity.",
publisher = "Wiley-V C H Verlag Gmbh, Weinheim",
journal = "CHEMISTRYSELECT",
title = "Electron Delocalization in Electron-Deficient Alkenes and Push-Pull Alkenes",
volume = "2",
number = "1",
pages = "42-50",
doi = "10.1002/slct.201601661"
}

Džambaski, Z.,& Baranac-Stojanović, M.. (2017). Electron Delocalization in Electron-Deficient Alkenes and Push-Pull Alkenes. in CHEMISTRYSELECT
Wiley-V C H Verlag Gmbh, Weinheim., 2(1), 42-50.
https://doi.org/10.1002/slct.201601661

Džambaski Z, Baranac-Stojanović M. Electron Delocalization in Electron-Deficient Alkenes and Push-Pull Alkenes. in CHEMISTRYSELECT. 2017;2(1):42-50.
doi:10.1002/slct.201601661 .

Džambaski, Zdravko, Baranac-Stojanović, Marija, "Electron Delocalization in Electron-Deficient Alkenes and Push-Pull Alkenes" in CHEMISTRYSELECT, 2, no. 1 (2017):42-50,
https://doi.org/10.1002/slct.201601661 . .

TY  - JOUR
AU  - Stojanović, Milovan
AU  - Baranac-Stojanović, Marija
PY  - 2016
UR  - https://cherry.chem.bg.ac.rs/handle/123456789/2022
AB  - Substitution of a CH group in benzene with nitrogen has a little effect on its aromaticity (Wang et al, Org. Lett. 2010, 12, 4824). How does the same type of substitution affect aromatic character of the three isomeric azaborines? Does further protonation change aromaticity of diazaborines? This work is aimed at answering these questions. Such a knowledge should be of interest for further exploration and application of BN/CC isosterism. Aromaticity of diazaborines and their protonated forms is studied with the aid of four aromaticity indices, HOMA, NICS(0)(pi zz), PDI and ECRE. Generally, NICS(0)(pi zz) and PDI point to similar aromaticity of diazaborines and their parent azaborines, while HOMA and ECRE indicate some changes. Thus, aromaticity of 1,2-azaborine slightly decreases/increases when CH meta/ortho,para to B is substituted with nitrogen. Aromaticity of the most aromatic 1,3-azaborine remains almost unchanged when CH meta to B and N is replaced with nitrogen, and becomes slightly weaker when any other CH group is substituted with nitrogen. Replacement of the CH ortho to N in 1,4-azaborine does not change much its cyclic delocalization, while replacement of the CH ortho to B leads to smaller cyclic delocalization. Protonated forms are either of similar or decreased aromaticity compared with neutral molecules.
PB  - Amer Chemical Soc, Washington
T2  - Journal of Organic Chemistry
T1  - Aromaticity of Diazaborines and Their Protonated Forms
VL  - 81
IS  - 1
SP  - 197
EP  - 205
DO  - 10.1021/acs.joc.5b02499
ER  - 

@article{
author = "Stojanović, Milovan and Baranac-Stojanović, Marija",
year = "2016",
abstract = "Substitution of a CH group in benzene with nitrogen has a little effect on its aromaticity (Wang et al, Org. Lett. 2010, 12, 4824). How does the same type of substitution affect aromatic character of the three isomeric azaborines? Does further protonation change aromaticity of diazaborines? This work is aimed at answering these questions. Such a knowledge should be of interest for further exploration and application of BN/CC isosterism. Aromaticity of diazaborines and their protonated forms is studied with the aid of four aromaticity indices, HOMA, NICS(0)(pi zz), PDI and ECRE. Generally, NICS(0)(pi zz) and PDI point to similar aromaticity of diazaborines and their parent azaborines, while HOMA and ECRE indicate some changes. Thus, aromaticity of 1,2-azaborine slightly decreases/increases when CH meta/ortho,para to B is substituted with nitrogen. Aromaticity of the most aromatic 1,3-azaborine remains almost unchanged when CH meta to B and N is replaced with nitrogen, and becomes slightly weaker when any other CH group is substituted with nitrogen. Replacement of the CH ortho to N in 1,4-azaborine does not change much its cyclic delocalization, while replacement of the CH ortho to B leads to smaller cyclic delocalization. Protonated forms are either of similar or decreased aromaticity compared with neutral molecules.",
publisher = "Amer Chemical Soc, Washington",
journal = "Journal of Organic Chemistry",
title = "Aromaticity of Diazaborines and Their Protonated Forms",
volume = "81",
number = "1",
pages = "197-205",
doi = "10.1021/acs.joc.5b02499"
}

Stojanović, M.,& Baranac-Stojanović, M.. (2016). Aromaticity of Diazaborines and Their Protonated Forms. in Journal of Organic Chemistry
Amer Chemical Soc, Washington., 81(1), 197-205.
https://doi.org/10.1021/acs.joc.5b02499

Stojanović M, Baranac-Stojanović M. Aromaticity of Diazaborines and Their Protonated Forms. in Journal of Organic Chemistry. 2016;81(1):197-205.
doi:10.1021/acs.joc.5b02499 .

Stojanović, Milovan, Baranac-Stojanović, Marija, "Aromaticity of Diazaborines and Their Protonated Forms" in Journal of Organic Chemistry, 81, no. 1 (2016):197-205,
https://doi.org/10.1021/acs.joc.5b02499 . .

TY  - DATA
AU  - Stojanović, Milovan
AU  - Baranac-Stojanović, Marija
PY  - 2016
UR  - https://cherry.chem.bg.ac.rs/handle/123456789/3372
PB  - Amer Chemical Soc, Washington
T2  - Journal of Organic Chemistry
T1  - Supplementary material for the article: Stojanović, M.; Baranac-Stojanović, M. Aromaticity of Diazaborines and Their Protonated Forms. J. Org. Chem. 2016, 81 (1), 197–205. https://doi.org/10.1021/acs.joc.5b02499
UR  - https://hdl.handle.net/21.15107/rcub_cherry_3372
ER  - 

@misc{
author = "Stojanović, Milovan and Baranac-Stojanović, Marija",
year = "2016",
publisher = "Amer Chemical Soc, Washington",
journal = "Journal of Organic Chemistry",
title = "Supplementary material for the article: Stojanović, M.; Baranac-Stojanović, M. Aromaticity of Diazaborines and Their Protonated Forms. J. Org. Chem. 2016, 81 (1), 197–205. https://doi.org/10.1021/acs.joc.5b02499",
url = "https://hdl.handle.net/21.15107/rcub_cherry_3372"
}

Stojanović, M.,& Baranac-Stojanović, M.. (2016). Supplementary material for the article: Stojanović, M.; Baranac-Stojanović, M. Aromaticity of Diazaborines and Their Protonated Forms. J. Org. Chem. 2016, 81 (1), 197–205. https://doi.org/10.1021/acs.joc.5b02499. in Journal of Organic Chemistry
Amer Chemical Soc, Washington..
https://hdl.handle.net/21.15107/rcub_cherry_3372

Stojanović M, Baranac-Stojanović M. Supplementary material for the article: Stojanović, M.; Baranac-Stojanović, M. Aromaticity of Diazaborines and Their Protonated Forms. J. Org. Chem. 2016, 81 (1), 197–205. https://doi.org/10.1021/acs.joc.5b02499. in Journal of Organic Chemistry. 2016;.
https://hdl.handle.net/21.15107/rcub_cherry_3372 .

Stojanović, Milovan, Baranac-Stojanović, Marija, "Supplementary material for the article: Stojanović, M.; Baranac-Stojanović, M. Aromaticity of Diazaborines and Their Protonated Forms. J. Org. Chem. 2016, 81 (1), 197–205. https://doi.org/10.1021/acs.joc.5b02499" in Journal of Organic Chemistry (2016),
https://hdl.handle.net/21.15107/rcub_cherry_3372 .