TY  - JOUR
AU  - Baranac-Stojanović, Marija
AU  - Aleksić, Jovana
AU  - Stojanović, Milovan
PY  - 2023
UR  - https://cer.ihtm.bg.ac.rs/handle/123456789/7229
AB  - Computational investigation at the BHandHLYP/6-311+G(d,p) level of theory of the gas-phase tautomerism of 2- and 4-pyridones confirmed the slight prevalence of lactim in the case of the former, but its dominance in the case of the latter, as shown previously. Examination of aromaticity by using HOMA, EDDB, NBOdel, NICS and AICD led to the conclusion that tautomerization of 4-pyridone results in greater aromaticity gain. It is also driven by the Pauli repulsion relief, which was revealed by the tautomerization energy decomposition analysis. By contrast, in the case of 2-pyridone, lactim is favoured by orbital and electrostatic interactions and disfavoured by the Pauli repulsion. Aromaticity gain in this case is smaller. The position of the tautomeric equilibrium can be modulated by substituent inductive effects (Cl and F), inductive and resonance effects (NH2 and NO2), hydrogen bonding (NO2), and medium polarity, the increase of which increases lactam population.
PB  - Royal Society of Chemistry (RSC)
T2  - Organic & Biomolecular Chemistry
T1  - Theoretical investigation of tautomerism of 2- and 4-pyridones: origin, substituent and solvent effects
VL  - 22
IS  - 1
SP  - 144
EP  - 158
DO  - 10.1039/D3OB01588B
ER  - 

@article{
author = "Baranac-Stojanović, Marija and Aleksić, Jovana and Stojanović, Milovan",
year = "2023",
abstract = "Computational investigation at the BHandHLYP/6-311+G(d,p) level of theory of the gas-phase tautomerism of 2- and 4-pyridones confirmed the slight prevalence of lactim in the case of the former, but its dominance in the case of the latter, as shown previously. Examination of aromaticity by using HOMA, EDDB, NBOdel, NICS and AICD led to the conclusion that tautomerization of 4-pyridone results in greater aromaticity gain. It is also driven by the Pauli repulsion relief, which was revealed by the tautomerization energy decomposition analysis. By contrast, in the case of 2-pyridone, lactim is favoured by orbital and electrostatic interactions and disfavoured by the Pauli repulsion. Aromaticity gain in this case is smaller. The position of the tautomeric equilibrium can be modulated by substituent inductive effects (Cl and F), inductive and resonance effects (NH2 and NO2), hydrogen bonding (NO2), and medium polarity, the increase of which increases lactam population.",
publisher = "Royal Society of Chemistry (RSC)",
journal = "Organic & Biomolecular Chemistry",
title = "Theoretical investigation of tautomerism of 2- and 4-pyridones: origin, substituent and solvent effects",
volume = "22",
number = "1",
pages = "144-158",
doi = "10.1039/D3OB01588B"
}

Baranac-Stojanović, M., Aleksić, J.,& Stojanović, M.. (2023). Theoretical investigation of tautomerism of 2- and 4-pyridones: origin, substituent and solvent effects. in Organic & Biomolecular Chemistry
Royal Society of Chemistry (RSC)., 22(1), 144-158.
https://doi.org/10.1039/D3OB01588B

Baranac-Stojanović M, Aleksić J, Stojanović M. Theoretical investigation of tautomerism of 2- and 4-pyridones: origin, substituent and solvent effects. in Organic & Biomolecular Chemistry. 2023;22(1):144-158.
doi:10.1039/D3OB01588B .

Baranac-Stojanović, Marija, Aleksić, Jovana, Stojanović, Milovan, "Theoretical investigation of tautomerism of 2- and 4-pyridones: origin, substituent and solvent effects" in Organic & Biomolecular Chemistry, 22, no. 1 (2023):144-158,
https://doi.org/10.1039/D3OB01588B . .

TY  - JOUR
AU  - Aleksić, Jovana
AU  - Stojanović, Milovan
AU  - Bošković, Jakša
AU  - Baranac-Stojanović, Marija
PY  - 2023
UR  - https://cer.ihtm.bg.ac.rs/handle/123456789/5681
AB  - We present the green, highly atom-economical, solid-state silica gel-catalyzed synthesis of polysubstituted
1,4- and 1,2-dihydropyridines (DHPs) from commercially available materials, amines and ethyl propiolate.
The DHP skeleton was assembled by heating the reactants and silica gel in a closed vessel.
Aliphatic amines provided 1,4-isomers as the main or only DHP products, but the reactions of aromatic
amines yielded a mixture of 1,4- and 1,2-isomers. To the best of our knowledge, this is the first example
of the formation of a 1,2-DHP structure by the reaction of an amine with propiolic ester. Addition of
1 mass percent of H2SO4 to silica gel shifted the product distribution to 1,4-DHP as the main or the only
isomer obtained. Experimental and theoretical analyses led to the identification of two key intermediates
en route to DHPs and the explanation of the observed regioisomeric ratios. 1,2-DHPs show blue-cyan fluorescence
in MeOH with the quantum yield Φ = 0.10–0.22 relative to quinine sulfate Φ = 0.58 and 1,4-
DHPs show blue-violet fluorescence with Φ = 0.09–0.81.
PB  - Great Britain : Royal Society of Chemistry
T2  - Organic & Biomolecular Chemistry
T1  - Solid-state silica gel-catalyzed synthesis of fluorescent polysubstituted 1,4- and 1,2-dihydropyridines
DO  - 10.1039/d2ob02119f
ER  - 

@article{
author = "Aleksić, Jovana and Stojanović, Milovan and Bošković, Jakša and Baranac-Stojanović, Marija",
year = "2023",
abstract = "We present the green, highly atom-economical, solid-state silica gel-catalyzed synthesis of polysubstituted
1,4- and 1,2-dihydropyridines (DHPs) from commercially available materials, amines and ethyl propiolate.
The DHP skeleton was assembled by heating the reactants and silica gel in a closed vessel.
Aliphatic amines provided 1,4-isomers as the main or only DHP products, but the reactions of aromatic
amines yielded a mixture of 1,4- and 1,2-isomers. To the best of our knowledge, this is the first example
of the formation of a 1,2-DHP structure by the reaction of an amine with propiolic ester. Addition of
1 mass percent of H2SO4 to silica gel shifted the product distribution to 1,4-DHP as the main or the only
isomer obtained. Experimental and theoretical analyses led to the identification of two key intermediates
en route to DHPs and the explanation of the observed regioisomeric ratios. 1,2-DHPs show blue-cyan fluorescence
in MeOH with the quantum yield Φ = 0.10–0.22 relative to quinine sulfate Φ = 0.58 and 1,4-
DHPs show blue-violet fluorescence with Φ = 0.09–0.81.",
publisher = "Great Britain : Royal Society of Chemistry",
journal = "Organic & Biomolecular Chemistry",
title = "Solid-state silica gel-catalyzed synthesis of fluorescent polysubstituted 1,4- and 1,2-dihydropyridines",
doi = "10.1039/d2ob02119f"
}

Aleksić, J., Stojanović, M., Bošković, J.,& Baranac-Stojanović, M.. (2023). Solid-state silica gel-catalyzed synthesis of fluorescent polysubstituted 1,4- and 1,2-dihydropyridines. in Organic & Biomolecular Chemistry
Great Britain : Royal Society of Chemistry..
https://doi.org/10.1039/d2ob02119f

Aleksić J, Stojanović M, Bošković J, Baranac-Stojanović M. Solid-state silica gel-catalyzed synthesis of fluorescent polysubstituted 1,4- and 1,2-dihydropyridines. in Organic & Biomolecular Chemistry. 2023;.
doi:10.1039/d2ob02119f .

Aleksić, Jovana, Stojanović, Milovan, Bošković, Jakša, Baranac-Stojanović, Marija, "Solid-state silica gel-catalyzed synthesis of fluorescent polysubstituted 1,4- and 1,2-dihydropyridines" in Organic & Biomolecular Chemistry (2023),
https://doi.org/10.1039/d2ob02119f . .

TY  - JOUR
AU  - Aleksić, Jovana
AU  - Stojanović, Milovan
AU  - Bošković, Jakša
AU  - Baranac-Stojanović, Marija
PY  - 2023
UR  - https://cer.ihtm.bg.ac.rs/handle/123456789/5790
AB  - We present the green, highly atom-economical, solid-state silica gel-catalyzed synthesis of polysubstituted 1,4- and 1,2-dihydropyridines (DHPs) from commercially available materials, amines and ethyl propiolate. The DHP skeleton was assembled by heating the reactants and silica gel in a closed vessel. Aliphatic amines provided 1,4-isomers as the main or only DHP products, but the reactions of aromatic amines yielded a mixture of 1,4- and 1,2-isomers. To the best of our knowledge, this is the first example of the formation of a 1,2-DHP structure by the reaction of an amine with propiolic ester. Addition of 1 mass percent of H2SO4 to silica gel shifted the product distribution to 1,4-DHP as the main or the only isomer obtained. Experimental and theoretical analyses led to the identification of two key intermediates en route to DHPs and the explanation of the observed regioisomeric ratios. 1,2-DHPs show blue-cyan fluorescence in MeOH with the quantum yield Φ = 0.10-0.22 relative to quinine sulfate Φ = 0.58 and 1,4-DHPs show blue-violet fluorescence with Φ = 0.09-0.81.
PB  - Royal Society of Chemistry
T2  - Organic & biomolecular chemistry
T1  - Solid-state silica gel-catalyzed synthesis of fluorescent polysubstituted 1,4- and 1,2-dihydropyridines
VL  - 21
IS  - 6
SP  - 1187
EP  - 1205
DO  - 10.1039/d2ob02119f
ER  - 

@article{
author = "Aleksić, Jovana and Stojanović, Milovan and Bošković, Jakša and Baranac-Stojanović, Marija",
year = "2023",
abstract = "We present the green, highly atom-economical, solid-state silica gel-catalyzed synthesis of polysubstituted 1,4- and 1,2-dihydropyridines (DHPs) from commercially available materials, amines and ethyl propiolate. The DHP skeleton was assembled by heating the reactants and silica gel in a closed vessel. Aliphatic amines provided 1,4-isomers as the main or only DHP products, but the reactions of aromatic amines yielded a mixture of 1,4- and 1,2-isomers. To the best of our knowledge, this is the first example of the formation of a 1,2-DHP structure by the reaction of an amine with propiolic ester. Addition of 1 mass percent of H2SO4 to silica gel shifted the product distribution to 1,4-DHP as the main or the only isomer obtained. Experimental and theoretical analyses led to the identification of two key intermediates en route to DHPs and the explanation of the observed regioisomeric ratios. 1,2-DHPs show blue-cyan fluorescence in MeOH with the quantum yield Φ = 0.10-0.22 relative to quinine sulfate Φ = 0.58 and 1,4-DHPs show blue-violet fluorescence with Φ = 0.09-0.81.",
publisher = "Royal Society of Chemistry",
journal = "Organic & biomolecular chemistry",
title = "Solid-state silica gel-catalyzed synthesis of fluorescent polysubstituted 1,4- and 1,2-dihydropyridines",
volume = "21",
number = "6",
pages = "1187-1205",
doi = "10.1039/d2ob02119f"
}

Aleksić, J., Stojanović, M., Bošković, J.,& Baranac-Stojanović, M.. (2023). Solid-state silica gel-catalyzed synthesis of fluorescent polysubstituted 1,4- and 1,2-dihydropyridines. in Organic & biomolecular chemistry
Royal Society of Chemistry., 21(6), 1187-1205.
https://doi.org/10.1039/d2ob02119f

Aleksić J, Stojanović M, Bošković J, Baranac-Stojanović M. Solid-state silica gel-catalyzed synthesis of fluorescent polysubstituted 1,4- and 1,2-dihydropyridines. in Organic & biomolecular chemistry. 2023;21(6):1187-1205.
doi:10.1039/d2ob02119f .

Aleksić, Jovana, Stojanović, Milovan, Bošković, Jakša, Baranac-Stojanović, Marija, "Solid-state silica gel-catalyzed synthesis of fluorescent polysubstituted 1,4- and 1,2-dihydropyridines" in Organic & biomolecular chemistry, 21, no. 6 (2023):1187-1205,
https://doi.org/10.1039/d2ob02119f . .

TY  - JOUR
AU  - Aleksić, Jovana
AU  - Stojanović, Milovan
AU  - Baranac-Stojanović, Marija
PY  - 2022
UR  - https://cer.ihtm.bg.ac.rs/handle/123456789/5365
AB  - Aromaticity rules in the ground singlet state and the first excited triplet state are exactly opposite, as shown by Baird. Thus, (4n + 2)π electron annulenes are antiaromatic and 4nπ annulenes are aromatic in their triplet state. In this work, we employ quantum-mechanical calculations at the density functional theory (DFT) level to examine (anti)aromaticity of singlet and triplet corannulene dianion and dication in their bowl-shaped ground-state structure and planar transition-state structure. We find that singlet dianion contains aromatic hub and antiaromatic rim, whereas singlet dication is an antiaromatic system. This agrees with previous calculations of current density induced by perpendicular magnetic field. For triplet dianion, we find that it can be described as having aromatic rim and nonaromatic hub. Triplet dication was found to be nonaromatic, though in planar transition-state structure, locally and semiglobally antiaromatic naphthalene subunit and aromatic central ring can be discerned.
PB  - John Wiley and Sons Ltd
T2  - Journal of Physical Organic Chemistry
T1  - Aromaticity study of singlet- and triplet-state corannulene dianion and dication
DO  - 10.1002/poc.4434
ER  - 

@article{
author = "Aleksić, Jovana and Stojanović, Milovan and Baranac-Stojanović, Marija",
year = "2022",
abstract = "Aromaticity rules in the ground singlet state and the first excited triplet state are exactly opposite, as shown by Baird. Thus, (4n + 2)π electron annulenes are antiaromatic and 4nπ annulenes are aromatic in their triplet state. In this work, we employ quantum-mechanical calculations at the density functional theory (DFT) level to examine (anti)aromaticity of singlet and triplet corannulene dianion and dication in their bowl-shaped ground-state structure and planar transition-state structure. We find that singlet dianion contains aromatic hub and antiaromatic rim, whereas singlet dication is an antiaromatic system. This agrees with previous calculations of current density induced by perpendicular magnetic field. For triplet dianion, we find that it can be described as having aromatic rim and nonaromatic hub. Triplet dication was found to be nonaromatic, though in planar transition-state structure, locally and semiglobally antiaromatic naphthalene subunit and aromatic central ring can be discerned.",
publisher = "John Wiley and Sons Ltd",
journal = "Journal of Physical Organic Chemistry",
title = "Aromaticity study of singlet- and triplet-state corannulene dianion and dication",
doi = "10.1002/poc.4434"
}

Aleksić, J., Stojanović, M.,& Baranac-Stojanović, M.. (2022). Aromaticity study of singlet- and triplet-state corannulene dianion and dication. in Journal of Physical Organic Chemistry
John Wiley and Sons Ltd..
https://doi.org/10.1002/poc.4434

Aleksić J, Stojanović M, Baranac-Stojanović M. Aromaticity study of singlet- and triplet-state corannulene dianion and dication. in Journal of Physical Organic Chemistry. 2022;.
doi:10.1002/poc.4434 .

Aleksić, Jovana, Stojanović, Milovan, Baranac-Stojanović, Marija, "Aromaticity study of singlet- and triplet-state corannulene dianion and dication" in Journal of Physical Organic Chemistry (2022),
https://doi.org/10.1002/poc.4434 . .

TY  - JOUR
AU  - Baranac-Stojanović, Marija
AU  - Stojanović, Milovan
AU  - Aleksić, Jovana
PY  - 2022
UR  - https://cer.ihtm.bg.ac.rs/handle/123456789/5408
AB  - By employing density functional theory (DFT)
calculations we show that mono- and disilicon substitution in
polycyclic aromatic hydrocarbons, having two to four
benzene units, quenches their triplet state antiaromaticity by
creating Huckel aromatic (poly)benzenoid subunit(s) and
weakly antiaromatic, or almost nonaromatic silacycle. Therefore,
such systems are predicted to be globally aromatic in
both the ground state and the first excited triplet state.
Putting the silicon atom(s) into various positions of a hydrocarbon
provides an opportunity to tune the singlet-triplet
energy gaps. They depend on the global aromaticity degree
which, in turn, depends on the type of aromatic carbocyclic
subunit(s) and the extent of their aromaticity. On the basis of
the set of studied compounds, some preliminary rules on
how to regulate the extent of global, semiglobal and local
aromaticity are proposed. The results of this work extend the
importance of Huckel aromaticity concept to excited triplet
states which are usually characterized by the Baird type of
(anti)aromaticity.
PB  - Wiley
T2  - Chemistry- An Asian Journal
T1  - Revival of Hückel Aromatic (Poly)benzenoid Subunits in Triplet State Polycyclic Aromatic Hydrocarbons by Silicon Substitution
SP  - e202101261
DO  - 10.1002/asia.202101261
ER  - 

@article{
author = "Baranac-Stojanović, Marija and Stojanović, Milovan and Aleksić, Jovana",
year = "2022",
abstract = "By employing density functional theory (DFT)
calculations we show that mono- and disilicon substitution in
polycyclic aromatic hydrocarbons, having two to four
benzene units, quenches their triplet state antiaromaticity by
creating Huckel aromatic (poly)benzenoid subunit(s) and
weakly antiaromatic, or almost nonaromatic silacycle. Therefore,
such systems are predicted to be globally aromatic in
both the ground state and the first excited triplet state.
Putting the silicon atom(s) into various positions of a hydrocarbon
provides an opportunity to tune the singlet-triplet
energy gaps. They depend on the global aromaticity degree
which, in turn, depends on the type of aromatic carbocyclic
subunit(s) and the extent of their aromaticity. On the basis of
the set of studied compounds, some preliminary rules on
how to regulate the extent of global, semiglobal and local
aromaticity are proposed. The results of this work extend the
importance of Huckel aromaticity concept to excited triplet
states which are usually characterized by the Baird type of
(anti)aromaticity.",
publisher = "Wiley",
journal = "Chemistry- An Asian Journal",
title = "Revival of Hückel Aromatic (Poly)benzenoid Subunits in Triplet State Polycyclic Aromatic Hydrocarbons by Silicon Substitution",
pages = "e202101261",
doi = "10.1002/asia.202101261"
}

Baranac-Stojanović, M., Stojanović, M.,& Aleksić, J.. (2022). Revival of Hückel Aromatic (Poly)benzenoid Subunits in Triplet State Polycyclic Aromatic Hydrocarbons by Silicon Substitution. in Chemistry- An Asian Journal
Wiley., e202101261.
https://doi.org/10.1002/asia.202101261

Baranac-Stojanović M, Stojanović M, Aleksić J. Revival of Hückel Aromatic (Poly)benzenoid Subunits in Triplet State Polycyclic Aromatic Hydrocarbons by Silicon Substitution. in Chemistry- An Asian Journal. 2022;:e202101261.
doi:10.1002/asia.202101261 .

Baranac-Stojanović, Marija, Stojanović, Milovan, Aleksić, Jovana, "Revival of Hückel Aromatic (Poly)benzenoid Subunits in Triplet State Polycyclic Aromatic Hydrocarbons by Silicon Substitution" in Chemistry- An Asian Journal (2022):e202101261,
https://doi.org/10.1002/asia.202101261 . .

TY  - JOUR
AU  - Baranac-Stojanović, Marija
AU  - Stojanović, Milovan
AU  - Aleksić, Jovana
PY  - 2021
UR  - https://cer.ihtm.bg.ac.rs/handle/123456789/4483
AB  - Aromaticity–antiaromaticity switch upon singlet–triplet transition of some biologically and synthetically
important monoheterocycles (heteroatom = N, O, Si, P, and S) derived from benzene, naphthalene and
anthracene was studied by employing energetic, magnetic and structural aromaticity criteria, at the
density functional theory (DFT) level. The relationship between spin density distribution, (anti)aromaticity
and singlet–triplet energy gaps, in the studied molecules, was found. In general, spin delocalization
results in antiaromaticity, spin density localization to one ring in bi- and tricycles localizes antiaromaticity
and spin localization on a heteroatom reduces global and local antiaromaticity. The latter reaches
nonaromaticity in the case of silicon atoms which have larger orbitals and show more tendency to
accept unpaired electrons. Spin density localization in bi- and tricycles allows benzene subunit(s) to
develop local aromaticity, which, when combined with nonaromatic silacycle and weak global
antiaromaticity, results in overall triplet state weak aromaticity. The singlet–triplet energy gaps decrease
with a decrease in the triplet state antiaromaticity and are the lowest for silicon-containing compounds.
PB  - Royal Society  of Chemistry
T2  - New Journal of Chemistry
T1  - Triplet state (anti)aromaticity of some monoheterocyclic analogues of benzene, naphthalene and anthracene
VL  - 45
IS  - 11
SP  - 5060
EP  - 5074
DO  - 10.1039/d1nj00207d
ER  - 

@article{
author = "Baranac-Stojanović, Marija and Stojanović, Milovan and Aleksić, Jovana",
year = "2021",
abstract = "Aromaticity–antiaromaticity switch upon singlet–triplet transition of some biologically and synthetically
important monoheterocycles (heteroatom = N, O, Si, P, and S) derived from benzene, naphthalene and
anthracene was studied by employing energetic, magnetic and structural aromaticity criteria, at the
density functional theory (DFT) level. The relationship between spin density distribution, (anti)aromaticity
and singlet–triplet energy gaps, in the studied molecules, was found. In general, spin delocalization
results in antiaromaticity, spin density localization to one ring in bi- and tricycles localizes antiaromaticity
and spin localization on a heteroatom reduces global and local antiaromaticity. The latter reaches
nonaromaticity in the case of silicon atoms which have larger orbitals and show more tendency to
accept unpaired electrons. Spin density localization in bi- and tricycles allows benzene subunit(s) to
develop local aromaticity, which, when combined with nonaromatic silacycle and weak global
antiaromaticity, results in overall triplet state weak aromaticity. The singlet–triplet energy gaps decrease
with a decrease in the triplet state antiaromaticity and are the lowest for silicon-containing compounds.",
publisher = "Royal Society  of Chemistry",
journal = "New Journal of Chemistry",
title = "Triplet state (anti)aromaticity of some monoheterocyclic analogues of benzene, naphthalene and anthracene",
volume = "45",
number = "11",
pages = "5060-5074",
doi = "10.1039/d1nj00207d"
}

Baranac-Stojanović, M., Stojanović, M.,& Aleksić, J.. (2021). Triplet state (anti)aromaticity of some monoheterocyclic analogues of benzene, naphthalene and anthracene. in New Journal of Chemistry
Royal Society  of Chemistry., 45(11), 5060-5074.
https://doi.org/10.1039/d1nj00207d

Baranac-Stojanović M, Stojanović M, Aleksić J. Triplet state (anti)aromaticity of some monoheterocyclic analogues of benzene, naphthalene and anthracene. in New Journal of Chemistry. 2021;45(11):5060-5074.
doi:10.1039/d1nj00207d .

Baranac-Stojanović, Marija, Stojanović, Milovan, Aleksić, Jovana, "Triplet state (anti)aromaticity of some monoheterocyclic analogues of benzene, naphthalene and anthracene" in New Journal of Chemistry, 45, no. 11 (2021):5060-5074,
https://doi.org/10.1039/d1nj00207d . .

TY  - DATA
AU  - Baranac-Stojanović, Marija
AU  - Stojanović, Milovan
AU  - Aleksić, Jovana
PY  - 2021
UR  - https://cer.ihtm.bg.ac.rs/handle/123456789/4484
AB  - Figure S1. Correlation of B3LYP and PBE0, CAM-B3LYP, M062X and MP2 bond lengths for all monocycles studied. Figure S2. Correlations between aromaticity indices calculated for monocycles. Tables S1-S4. Comparison of aromaticity indices calculated with different methods. Figures S3-S28. ACID plots of studied compounds. S4 Absolute energies and x, y, z coordinates of optimized structures. S18
PB  - Royal Society  of Chemistry
T2  - New Journal of Chemistry
T1  - Supplementary information for: "Triplet state (anti)aromaticity of some monoheterocyclic analogues of benzene, naphthalene and anthracene"
UR  - https://hdl.handle.net/21.15107/rcub_cer_4484
ER  - 

@misc{
author = "Baranac-Stojanović, Marija and Stojanović, Milovan and Aleksić, Jovana",
year = "2021",
abstract = "Figure S1. Correlation of B3LYP and PBE0, CAM-B3LYP, M062X and MP2 bond lengths for all monocycles studied. Figure S2. Correlations between aromaticity indices calculated for monocycles. Tables S1-S4. Comparison of aromaticity indices calculated with different methods. Figures S3-S28. ACID plots of studied compounds. S4 Absolute energies and x, y, z coordinates of optimized structures. S18",
publisher = "Royal Society  of Chemistry",
journal = "New Journal of Chemistry",
title = "Supplementary information for: "Triplet state (anti)aromaticity of some monoheterocyclic analogues of benzene, naphthalene and anthracene"",
url = "https://hdl.handle.net/21.15107/rcub_cer_4484"
}

Baranac-Stojanović, M., Stojanović, M.,& Aleksić, J.. (2021). Supplementary information for: "Triplet state (anti)aromaticity of some monoheterocyclic analogues of benzene, naphthalene and anthracene". in New Journal of Chemistry
Royal Society  of Chemistry..
https://hdl.handle.net/21.15107/rcub_cer_4484

Baranac-Stojanović M, Stojanović M, Aleksić J. Supplementary information for: "Triplet state (anti)aromaticity of some monoheterocyclic analogues of benzene, naphthalene and anthracene". in New Journal of Chemistry. 2021;.
https://hdl.handle.net/21.15107/rcub_cer_4484 .

Baranac-Stojanović, Marija, Stojanović, Milovan, Aleksić, Jovana, "Supplementary information for: "Triplet state (anti)aromaticity of some monoheterocyclic analogues of benzene, naphthalene and anthracene"" in New Journal of Chemistry (2021),
https://hdl.handle.net/21.15107/rcub_cer_4484 .

TY  - JOUR
AU  - Stojanović, Milovan
AU  - Bugarski, Slobodan
AU  - Baranac-Stojanović, Marija
PY  - 2020
UR  - https://cer.ihtm.bg.ac.rs/handle/123456789/4020
AB  - 2,3-Dihydro-4-pyridone skeleton is an important building block in organic synthesis because it features several reaction sites with nucleophilic or electrophilic properties. Herein, we disclose a method for its formation by intramolecular cyclization of ester-tethered enaminones, which can easily be synthesized from readily available materials, such as amines, activated alkynes, and activated alkenes. 2,3-Dihydro-4-pyridones have been isolated in 41–90% yields. We also demonstrate the transformation of these heterocycles into another important class of compounds, 4-pyridones, by utilizing 2,3,5,6-tetrachloro-p-benzoquinone (chloranil) as an oxidizing agent. The latter products were isolated in 65–94% yields.
PB  - American Chemical Society (ACS)
T2  - The Journal of Organic Chemistry
T1  - Synthesis of 2,3-Dihydro-4-pyridones and 4-Pyridones by the Cyclization Reaction of Ester-Tethered Enaminones
VL  - 85
IS  - 21
SP  - 13495
EP  - 13507
DO  - 10.1021/acs.joc.0c01537
ER  - 

@article{
author = "Stojanović, Milovan and Bugarski, Slobodan and Baranac-Stojanović, Marija",
year = "2020",
abstract = "2,3-Dihydro-4-pyridone skeleton is an important building block in organic synthesis because it features several reaction sites with nucleophilic or electrophilic properties. Herein, we disclose a method for its formation by intramolecular cyclization of ester-tethered enaminones, which can easily be synthesized from readily available materials, such as amines, activated alkynes, and activated alkenes. 2,3-Dihydro-4-pyridones have been isolated in 41–90% yields. We also demonstrate the transformation of these heterocycles into another important class of compounds, 4-pyridones, by utilizing 2,3,5,6-tetrachloro-p-benzoquinone (chloranil) as an oxidizing agent. The latter products were isolated in 65–94% yields.",
publisher = "American Chemical Society (ACS)",
journal = "The Journal of Organic Chemistry",
title = "Synthesis of 2,3-Dihydro-4-pyridones and 4-Pyridones by the Cyclization Reaction of Ester-Tethered Enaminones",
volume = "85",
number = "21",
pages = "13495-13507",
doi = "10.1021/acs.joc.0c01537"
}

Stojanović, M., Bugarski, S.,& Baranac-Stojanović, M.. (2020). Synthesis of 2,3-Dihydro-4-pyridones and 4-Pyridones by the Cyclization Reaction of Ester-Tethered Enaminones. in The Journal of Organic Chemistry
American Chemical Society (ACS)., 85(21), 13495-13507.
https://doi.org/10.1021/acs.joc.0c01537

Stojanović M, Bugarski S, Baranac-Stojanović M. Synthesis of 2,3-Dihydro-4-pyridones and 4-Pyridones by the Cyclization Reaction of Ester-Tethered Enaminones. in The Journal of Organic Chemistry. 2020;85(21):13495-13507.
doi:10.1021/acs.joc.0c01537 .

Stojanović, Milovan, Bugarski, Slobodan, Baranac-Stojanović, Marija, "Synthesis of 2,3-Dihydro-4-pyridones and 4-Pyridones by the Cyclization Reaction of Ester-Tethered Enaminones" in The Journal of Organic Chemistry, 85, no. 21 (2020):13495-13507,
https://doi.org/10.1021/acs.joc.0c01537 . .

TY  - JOUR
AU  - Baranac-Stojanović, Marija
AU  - Stojanović, Milovan
PY  - 2019
UR  - https://cer.ihtm.bg.ac.rs/handle/123456789/2945
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 NH2 group from the usual p-electron donor to a p-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 NLP in the plane of the ring and the NH bonds in a favourable spatial position to act as acceptors of p-electron density
PB  - Royal Society of Chemistry (RSC)
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 NH2 group from the usual p-electron donor to a p-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 NLP in the plane of the ring and the NH bonds in a favourable spatial position to act as acceptors of p-electron density",
publisher = "Royal Society of Chemistry (RSC)",
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 (RSC)., 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://cer.ihtm.bg.ac.rs/handle/123456789/2946
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 NH2 group from the usual p-electron donor to a p-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 NLP in the plane of the ring and the NH bonds in a favourable spatial position to act as acceptors of p-electron density
PB  - Royal Society of Chemistry (RSC)
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 NH2 group from the usual p-electron donor to a p-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 NLP in the plane of the ring and the NH bonds in a favourable spatial position to act as acceptors of p-electron density",
publisher = "Royal Society of Chemistry (RSC)",
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 (RSC)., 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://cer.ihtm.bg.ac.rs/handle/123456789/2960
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://cer.ihtm.bg.ac.rs/handle/123456789/2961
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  - Stojanović, Milovan
AU  - Baranac-Stojanović, Marija
PY  - 2018
UR  - https://cer.ihtm.bg.ac.rs/handle/123456789/2386
AB  - Relatively scarce literature data on BN/CC isosterism in 4nπ-electronic systems have prompted us to investigate theoretically the influence of BN pair position within the central butadiene fragment of dibenzo[a,e]pentalene on two fundamental molecular properties: stability and (anti)aromaticity. It was found that stability and aromaticity follow the same trend only for BN-orientational isomers. The source of different stability of other isomers was examined first by an analysis of bond types and their dissociation energies and then by isomerization energy decomposition analysis and was explained in terms of classical electrostatic interactions, quantum-mechanical orbital interactions, structural changes and electronic changes (transition from charge-separated π-system to the neutral one). (Anti)aromaticity was investigated by using three kinds of indices, HOMA, FLUπ, and NICS(1)zz, which indicated that delocalization at the central pentalene motif is almost unaffected by various BN arrangements, molecular perimeter is slightly affected, while the most affected subunits are five-membered rings and benzene-fused five-membered rings containing only one heteroatom.
PB  - Wiley-VCH Verlag
T2  - European Journal of Organic Chemistry
T1  - Analysis of Stability and (Anti)aromaticity of BN-Dibenzo[a,e]pentalenes
VL  - 2018
IS  - 45
SP  - 6230
EP  - 6240
DO  - 10.1002/ejoc.201801047
ER  - 

@article{
author = "Stojanović, Milovan and Baranac-Stojanović, Marija",
year = "2018",
abstract = "Relatively scarce literature data on BN/CC isosterism in 4nπ-electronic systems have prompted us to investigate theoretically the influence of BN pair position within the central butadiene fragment of dibenzo[a,e]pentalene on two fundamental molecular properties: stability and (anti)aromaticity. It was found that stability and aromaticity follow the same trend only for BN-orientational isomers. The source of different stability of other isomers was examined first by an analysis of bond types and their dissociation energies and then by isomerization energy decomposition analysis and was explained in terms of classical electrostatic interactions, quantum-mechanical orbital interactions, structural changes and electronic changes (transition from charge-separated π-system to the neutral one). (Anti)aromaticity was investigated by using three kinds of indices, HOMA, FLUπ, and NICS(1)zz, which indicated that delocalization at the central pentalene motif is almost unaffected by various BN arrangements, molecular perimeter is slightly affected, while the most affected subunits are five-membered rings and benzene-fused five-membered rings containing only one heteroatom.",
publisher = "Wiley-VCH Verlag",
journal = "European Journal of Organic Chemistry",
title = "Analysis of Stability and (Anti)aromaticity of BN-Dibenzo[a,e]pentalenes",
volume = "2018",
number = "45",
pages = "6230-6240",
doi = "10.1002/ejoc.201801047"
}

Stojanović, M.,& Baranac-Stojanović, M.. (2018). Analysis of Stability and (Anti)aromaticity of BN-Dibenzo[a,e]pentalenes. in European Journal of Organic Chemistry
Wiley-VCH Verlag., 2018(45), 6230-6240.
https://doi.org/10.1002/ejoc.201801047

Stojanović M, Baranac-Stojanović M. Analysis of Stability and (Anti)aromaticity of BN-Dibenzo[a,e]pentalenes. in European Journal of Organic Chemistry. 2018;2018(45):6230-6240.
doi:10.1002/ejoc.201801047 .

Stojanović, Milovan, Baranac-Stojanović, Marija, "Analysis of Stability and (Anti)aromaticity of BN-Dibenzo[a,e]pentalenes" in European Journal of Organic Chemistry, 2018, no. 45 (2018):6230-6240,
https://doi.org/10.1002/ejoc.201801047 . .

TY  - JOUR
AU  - Stojanović, Milovan
AU  - Baranac-Stojanović, Marija
PY  - 2018
UR  - https://cer.ihtm.bg.ac.rs/handle/123456789/2432
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://cer.ihtm.bg.ac.rs/handle/123456789/2451
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://cer.ihtm.bg.ac.rs/handle/123456789/2970
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://cer.ihtm.bg.ac.rs/handle/123456789/3135
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  - DATA
AU  - Stojanović, Milovan
AU  - Baranac-Stojanović, Marija
PY  - 2018
UR  - https://cer.ihtm.bg.ac.rs/handle/123456789/4477
AB  - Table S1. Experimental and calculated bond lengths and bond angles for 1,4 isomer of BN-dibenzopentalene; Table S2. Spin densities in diradical state of 1,3 isomer of BN-dibenzopentalene obtained by Hirshfeld population analysis; Figure S1. Relative energies of six isomeric BN-dibenzopentalenes, BN-butadienes and BN-pentalenes; Figure S2. NICS-XY scans. Section S1: Comparison of (anti)aromaticity of various isomers of BN-dibenzopentalenes. Absolute energies and X, Y, Z coordinates of optimized structures.
PB  - Wiley
T2  - European Journal of Organic Chemistry
T1  - Supporting information for: "Analysis of Stability and (Anti)aromaticity of BN-Dibenzo[a,e]pentalenes"
UR  - https://hdl.handle.net/21.15107/rcub_cer_4477
ER  - 

@misc{
author = "Stojanović, Milovan and Baranac-Stojanović, Marija",
year = "2018",
abstract = "Table S1. Experimental and calculated bond lengths and bond angles for 1,4 isomer of BN-dibenzopentalene; Table S2. Spin densities in diradical state of 1,3 isomer of BN-dibenzopentalene obtained by Hirshfeld population analysis; Figure S1. Relative energies of six isomeric BN-dibenzopentalenes, BN-butadienes and BN-pentalenes; Figure S2. NICS-XY scans. Section S1: Comparison of (anti)aromaticity of various isomers of BN-dibenzopentalenes. Absolute energies and X, Y, Z coordinates of optimized structures.",
publisher = "Wiley",
journal = "European Journal of Organic Chemistry",
title = "Supporting information for: "Analysis of Stability and (Anti)aromaticity of BN-Dibenzo[a,e]pentalenes"",
url = "https://hdl.handle.net/21.15107/rcub_cer_4477"
}

Stojanović, M.,& Baranac-Stojanović, M.. (2018). Supporting information for: "Analysis of Stability and (Anti)aromaticity of BN-Dibenzo[a,e]pentalenes". in European Journal of Organic Chemistry
Wiley..
https://hdl.handle.net/21.15107/rcub_cer_4477

Stojanović M, Baranac-Stojanović M. Supporting information for: "Analysis of Stability and (Anti)aromaticity of BN-Dibenzo[a,e]pentalenes". in European Journal of Organic Chemistry. 2018;.
https://hdl.handle.net/21.15107/rcub_cer_4477 .

Stojanović, Milovan, Baranac-Stojanović, Marija, "Supporting information for: "Analysis of Stability and (Anti)aromaticity of BN-Dibenzo[a,e]pentalenes"" in European Journal of Organic Chemistry (2018),
https://hdl.handle.net/21.15107/rcub_cer_4477 .

TY  - DATA
AU  - Stojanović, Milovan
AU  - Baranac-Stojanović, Marija
PY  - 2018
UR  - https://cer.ihtm.bg.ac.rs/handle/123456789/4491
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 Society for Chemistry
T2  - New Journal of Chemistry
T1  - Supplementary Material for: "Mono BN-substituted analogues of naphthalene: a theoretical analysis of the effect of BN position on stability, aromaticity and frontier orbital energies"
DO  - 10.1039/c8nj01529e
ER  - 

@misc{
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 Society for Chemistry",
journal = "New Journal of Chemistry",
title = "Supplementary Material for: "Mono BN-substituted analogues of naphthalene: a theoretical analysis of the effect of BN position on stability, aromaticity and frontier orbital energies"",
doi = "10.1039/c8nj01529e"
}

Stojanović, M.,& Baranac-Stojanović, M.. (2018). Supplementary Material for: "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 Society for Chemistry..
https://doi.org/10.1039/c8nj01529e

Stojanović M, Baranac-Stojanović M. Supplementary Material for: "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;.
doi:10.1039/c8nj01529e .

Stojanović, Milovan, Baranac-Stojanović, Marija, "Supplementary Material for: "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),
https://doi.org/10.1039/c8nj01529e . .

TY  - JOUR
AU  - Baranac-Stojanović, Marija
AU  - Stojanović, Milovan
AU  - Aleksić, Jovana
PY  - 2017
UR  - https://cer.ihtm.bg.ac.rs/handle/123456789/2264
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  - JOUR
AU  - Baranac-Stojanović, Marija
AU  - Stojanović, Milovan
AU  - Aleksić, Jovana
PY  - 2017
UR  - https://cer.ihtm.bg.ac.rs/handle/123456789/2969
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  - JOUR
AU  - Stojanović, Milovan
AU  - Baranac-Stojanović, Marija
PY  - 2016
UR  - https://cer.ihtm.bg.ac.rs/handle/123456789/1974
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  - American Chemical Society (ACS)
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 = "American Chemical Society (ACS)",
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
American Chemical Society (ACS)., 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  - JOUR
AU  - Stojanović, Milovan
AU  - Aleksić, Jovana
AU  - Baranac-Stojanović, Marija
PY  - 2015
UR  - https://cer.ihtm.bg.ac.rs/handle/123456789/1628
AB  - The origin of the rotational barriers in n-butane and gauche conformational energy, the prototypes of steric repulsion, has been re-examined by using energy decomposition analysis. The Pauli repulsion was found to be an important factor, but not the source of the barriers and gauche/anti energy difference. Rather, it should be considered as a driving force for structural changes accompanying the rotation. The repulsion (steric) energy partly transfers into the deformation energy of ethyl fragments and also affects a decrease in electrostatic, orbital and dispersion interactions by inducing the structural changes, particularly the central CC bond lengthening, while it becomes less destabilizing during the anti-butane rotation.
PB  - Oxford : Pergamon-Elsevier Science Ltd
T2  - Tetrahedron
T1  - The effect of steric repulsion on the torsional potential of n-butane: a theoretical study
VL  - 71
IS  - 32
SP  - 5119
EP  - 5123
DO  - 10.1016/j.tet.2015.06.002
ER  - 

@article{
author = "Stojanović, Milovan and Aleksić, Jovana and Baranac-Stojanović, Marija",
year = "2015",
abstract = "The origin of the rotational barriers in n-butane and gauche conformational energy, the prototypes of steric repulsion, has been re-examined by using energy decomposition analysis. The Pauli repulsion was found to be an important factor, but not the source of the barriers and gauche/anti energy difference. Rather, it should be considered as a driving force for structural changes accompanying the rotation. The repulsion (steric) energy partly transfers into the deformation energy of ethyl fragments and also affects a decrease in electrostatic, orbital and dispersion interactions by inducing the structural changes, particularly the central CC bond lengthening, while it becomes less destabilizing during the anti-butane rotation.",
publisher = "Oxford : Pergamon-Elsevier Science Ltd",
journal = "Tetrahedron",
title = "The effect of steric repulsion on the torsional potential of n-butane: a theoretical study",
volume = "71",
number = "32",
pages = "5119-5123",
doi = "10.1016/j.tet.2015.06.002"
}

Stojanović, M., Aleksić, J.,& Baranac-Stojanović, M.. (2015). The effect of steric repulsion on the torsional potential of n-butane: a theoretical study. in Tetrahedron
Oxford : Pergamon-Elsevier Science Ltd., 71(32), 5119-5123.
https://doi.org/10.1016/j.tet.2015.06.002

Stojanović M, Aleksić J, Baranac-Stojanović M. The effect of steric repulsion on the torsional potential of n-butane: a theoretical study. in Tetrahedron. 2015;71(32):5119-5123.
doi:10.1016/j.tet.2015.06.002 .

Stojanović, Milovan, Aleksić, Jovana, Baranac-Stojanović, Marija, "The effect of steric repulsion on the torsional potential of n-butane: a theoretical study" in Tetrahedron, 71, no. 32 (2015):5119-5123,
https://doi.org/10.1016/j.tet.2015.06.002 . .

TY  - JOUR
AU  - Stojanović, Milovan
AU  - Baranac-Stojanović, Marija
PY  - 2015
UR  - https://cer.ihtm.bg.ac.rs/handle/123456789/1711
AB  - Various borenium ion affinities toward three ligands (L' = NH3, HCHO and Cl-) have been evaluated by DFT calculations in the gas-phase and in solvent (CH2Cl2). The gas-phase results have been rationalized on the basis of quantitative decomposition of the total binding energy into contributions from electrostatic, orbital, dispersion and Pauli interactions, and energy needed to deform the interacting fragments from their optimal geometry to that they adopt in an adduct. Twenty six borenium cations, differing in the type of the two R/R' substituents covalently bound to the boron atom and the neutral stabilizing ligand L, have been examined. With a few exceptions, the most important stabilizing interaction is electrostatic, more pronounced in the case of the charged ligand Cl-. Next come orbital interactions, involving the coordinate covalent bond formation, other charge transfer interactions between the cation and ligand, and polarization. Dispersion forces provide the smallest attraction, except in four complexes with long B-L' distances. We present how substituent (R/R')/ligand (L) variations affect binding enthalpies (Delta H)/energies (Delta E). Our results also show that the observed trend in the magnitudes of Delta Hs/Delta Es represents an interplay of the above mentioned (de) stabilizing energies, and can be explained by consideration of the boron-ligand distance and all charge/orbital interactions, rather than partial ones involving boron and ligand L'. Under solvent conditions, the Cl- affinities are drastically reduced and made very similar to NH3 affinities, but still larger than HCHO affinities.
PB  - Royal Soc Chemistry, Cambridge
T2  - RSC Advances
T1  - A theoretical study on borenium ion affinities toward ammonia, formaldehyde and chloride anions
VL  - 5
IS  - 93
SP  - 75895
EP  - 75910
DO  - 10.1039/c5ra13825f
ER  - 

@article{
author = "Stojanović, Milovan and Baranac-Stojanović, Marija",
year = "2015",
abstract = "Various borenium ion affinities toward three ligands (L' = NH3, HCHO and Cl-) have been evaluated by DFT calculations in the gas-phase and in solvent (CH2Cl2). The gas-phase results have been rationalized on the basis of quantitative decomposition of the total binding energy into contributions from electrostatic, orbital, dispersion and Pauli interactions, and energy needed to deform the interacting fragments from their optimal geometry to that they adopt in an adduct. Twenty six borenium cations, differing in the type of the two R/R' substituents covalently bound to the boron atom and the neutral stabilizing ligand L, have been examined. With a few exceptions, the most important stabilizing interaction is electrostatic, more pronounced in the case of the charged ligand Cl-. Next come orbital interactions, involving the coordinate covalent bond formation, other charge transfer interactions between the cation and ligand, and polarization. Dispersion forces provide the smallest attraction, except in four complexes with long B-L' distances. We present how substituent (R/R')/ligand (L) variations affect binding enthalpies (Delta H)/energies (Delta E). Our results also show that the observed trend in the magnitudes of Delta Hs/Delta Es represents an interplay of the above mentioned (de) stabilizing energies, and can be explained by consideration of the boron-ligand distance and all charge/orbital interactions, rather than partial ones involving boron and ligand L'. Under solvent conditions, the Cl- affinities are drastically reduced and made very similar to NH3 affinities, but still larger than HCHO affinities.",
publisher = "Royal Soc Chemistry, Cambridge",
journal = "RSC Advances",
title = "A theoretical study on borenium ion affinities toward ammonia, formaldehyde and chloride anions",
volume = "5",
number = "93",
pages = "75895-75910",
doi = "10.1039/c5ra13825f"
}

Stojanović, M.,& Baranac-Stojanović, M.. (2015). A theoretical study on borenium ion affinities toward ammonia, formaldehyde and chloride anions. in RSC Advances
Royal Soc Chemistry, Cambridge., 5(93), 75895-75910.
https://doi.org/10.1039/c5ra13825f

Stojanović M, Baranac-Stojanović M. A theoretical study on borenium ion affinities toward ammonia, formaldehyde and chloride anions. in RSC Advances. 2015;5(93):75895-75910.
doi:10.1039/c5ra13825f .

Stojanović, Milovan, Baranac-Stojanović, Marija, "A theoretical study on borenium ion affinities toward ammonia, formaldehyde and chloride anions" in RSC Advances, 5, no. 93 (2015):75895-75910,
https://doi.org/10.1039/c5ra13825f . .

TY  - JOUR
AU  - Baranac-Stojanović, Marija
AU  - Aleksić, Jovana
AU  - Stojanović, Milovan
PY  - 2015
UR  - https://cer.ihtm.bg.ac.rs/handle/123456789/1775
AB  - 2-Haloethanol and 2-haloethylamine (halogen = F, Cl) prefer gauche conformation. This preference is significantly increased upon protonation. Commonly used explanations are based on intramolecular hydrogen bonding and hyperconjugation. 1,2-Difluoroethane prefers gauche conformation, too, while gaseous 1-chloro-2-fluoroethane is more stable as the anti conformer. The origin of these conformational preferences has been investigated by a quantitative partitioning of the gauche/anti energy difference into contributions from electrostatic, orbital, dispersion and Pauli interactions, and structural changes accompanying the rotation. The results show that, with two exceptions, the most important contributor to the gauche preference is electrostatic attraction, which is larger in gauche forms relative to the anti ones. Next come orbital interactions, while dispersion forces provide the smallest stabilizing energy. These energy components override destabilizing Pauli interactions and energetically costly structural changes. All gauche preferences also benefit from stereoelectronic effects, except in protonated 2-chloroethanol which, instead, shows a significant Cl lone pair -> O-H antibond mixing, associated with hydrogen bonding. The increase in the Pauli repulsion upon anti to gauche isomerization is more pronounced for fluorine than for chlorine derivatives. Thus, the smaller gauche effect in chloro-compounds and the anti preference in 1-chloro-2-fluoroethane have their origin in the decrease in electrostatic and orbital stabilizing interactions, a drop in the former being more pronounced.
PB  - Royal Soc Chemistry, Cambridge
T2  - RSC Advances
T1  - Energy decomposition analysis of gauche preference in 2-haloethanol, 2-haloethylamine (halogen = F, Cl), their protonated forms and anti preference in 1-chloro-2-fluoroethane
VL  - 5
IS  - 29
SP  - 22980
EP  - 22995
DO  - 10.1039/c5ra01164g
ER  - 

@article{
author = "Baranac-Stojanović, Marija and Aleksić, Jovana and Stojanović, Milovan",
year = "2015",
abstract = "2-Haloethanol and 2-haloethylamine (halogen = F, Cl) prefer gauche conformation. This preference is significantly increased upon protonation. Commonly used explanations are based on intramolecular hydrogen bonding and hyperconjugation. 1,2-Difluoroethane prefers gauche conformation, too, while gaseous 1-chloro-2-fluoroethane is more stable as the anti conformer. The origin of these conformational preferences has been investigated by a quantitative partitioning of the gauche/anti energy difference into contributions from electrostatic, orbital, dispersion and Pauli interactions, and structural changes accompanying the rotation. The results show that, with two exceptions, the most important contributor to the gauche preference is electrostatic attraction, which is larger in gauche forms relative to the anti ones. Next come orbital interactions, while dispersion forces provide the smallest stabilizing energy. These energy components override destabilizing Pauli interactions and energetically costly structural changes. All gauche preferences also benefit from stereoelectronic effects, except in protonated 2-chloroethanol which, instead, shows a significant Cl lone pair -> O-H antibond mixing, associated with hydrogen bonding. The increase in the Pauli repulsion upon anti to gauche isomerization is more pronounced for fluorine than for chlorine derivatives. Thus, the smaller gauche effect in chloro-compounds and the anti preference in 1-chloro-2-fluoroethane have their origin in the decrease in electrostatic and orbital stabilizing interactions, a drop in the former being more pronounced.",
publisher = "Royal Soc Chemistry, Cambridge",
journal = "RSC Advances",
title = "Energy decomposition analysis of gauche preference in 2-haloethanol, 2-haloethylamine (halogen = F, Cl), their protonated forms and anti preference in 1-chloro-2-fluoroethane",
volume = "5",
number = "29",
pages = "22980-22995",
doi = "10.1039/c5ra01164g"
}

Baranac-Stojanović, M., Aleksić, J.,& Stojanović, M.. (2015). Energy decomposition analysis of gauche preference in 2-haloethanol, 2-haloethylamine (halogen = F, Cl), their protonated forms and anti preference in 1-chloro-2-fluoroethane. in RSC Advances
Royal Soc Chemistry, Cambridge., 5(29), 22980-22995.
https://doi.org/10.1039/c5ra01164g

Baranac-Stojanović M, Aleksić J, Stojanović M. Energy decomposition analysis of gauche preference in 2-haloethanol, 2-haloethylamine (halogen = F, Cl), their protonated forms and anti preference in 1-chloro-2-fluoroethane. in RSC Advances. 2015;5(29):22980-22995.
doi:10.1039/c5ra01164g .

Baranac-Stojanović, Marija, Aleksić, Jovana, Stojanović, Milovan, "Energy decomposition analysis of gauche preference in 2-haloethanol, 2-haloethylamine (halogen = F, Cl), their protonated forms and anti preference in 1-chloro-2-fluoroethane" in RSC Advances, 5, no. 29 (2015):22980-22995,
https://doi.org/10.1039/c5ra01164g . .