TY  - JOUR
AU  - Ajaj, Ismail
AU  - Markovski, Jasmina
AU  - Rančić, Milica
AU  - Mijin, Dusan
AU  - Milcić, Miloš
AU  - Jovanović, Maja
AU  - Marinković, Aleksandar
PY  - 2015
UR  - https://omorika.sfb.bg.ac.rs/handle/123456789/651
AB  - The state of the tautomeric equilibria of 2(6)-hydroxy-4-methyl-6(2)-oxo-1-(substituted phenyl)-1,2(1,6)-dihydropyridine-3-carbonitriles, 2-PY/6-PY, was evaluated using experimental and theoretical methodology. The experimental data were interpreted with the aid of time-dependent density functional (TD-DFT) method. Electron charge density was obtained by the use of Quantum Theory of Atoms in Molecules, i.e. Bader's analysis. Linear solvation energy relationships (LSER) rationalized solvent influence on tautomeric equilibrium. Linear free energy relationships (LFERs) were applied to the substituent-induced NMR chemical shifts (SCS) using SSP (single substituent parameter) and DSP (dual substituent parameter) model. Theoretical calculations and obtained correlations gave insight into the influence of molecular conformation on the transmission of substituent electronic effects, as well as on different solvent solute interactions, and the state of tautomeric equilibrium.
T2  - Spectrochimica Acta Part A-Molecular and Biomolecular Spectroscopy
T1  - Solvent and structural effects in tautomeric 2(6)-hydroxy-4-methyl-6(2)-oxo-1-(substituted phenyl)-1,2(1,6)-dihydropyridine-3-carbonitriles: UV, NMR and quantum chemical study
EP  - 585
SP  - 575
VL  - 150
DO  - 10.1016/j.saa.2015.05.055
UR  - conv_1172
ER  - 

@article{
author = "Ajaj, Ismail and Markovski, Jasmina and Rančić, Milica and Mijin, Dusan and Milcić, Miloš and Jovanović, Maja and Marinković, Aleksandar",
year = "2015",
abstract = "The state of the tautomeric equilibria of 2(6)-hydroxy-4-methyl-6(2)-oxo-1-(substituted phenyl)-1,2(1,6)-dihydropyridine-3-carbonitriles, 2-PY/6-PY, was evaluated using experimental and theoretical methodology. The experimental data were interpreted with the aid of time-dependent density functional (TD-DFT) method. Electron charge density was obtained by the use of Quantum Theory of Atoms in Molecules, i.e. Bader's analysis. Linear solvation energy relationships (LSER) rationalized solvent influence on tautomeric equilibrium. Linear free energy relationships (LFERs) were applied to the substituent-induced NMR chemical shifts (SCS) using SSP (single substituent parameter) and DSP (dual substituent parameter) model. Theoretical calculations and obtained correlations gave insight into the influence of molecular conformation on the transmission of substituent electronic effects, as well as on different solvent solute interactions, and the state of tautomeric equilibrium.",
journal = "Spectrochimica Acta Part A-Molecular and Biomolecular Spectroscopy",
title = "Solvent and structural effects in tautomeric 2(6)-hydroxy-4-methyl-6(2)-oxo-1-(substituted phenyl)-1,2(1,6)-dihydropyridine-3-carbonitriles: UV, NMR and quantum chemical study",
pages = "585-575",
volume = "150",
doi = "10.1016/j.saa.2015.05.055",
url = "conv_1172"
}

Ajaj, I., Markovski, J., Rančić, M., Mijin, D., Milcić, M., Jovanović, M.,& Marinković, A.. (2015). Solvent and structural effects in tautomeric 2(6)-hydroxy-4-methyl-6(2)-oxo-1-(substituted phenyl)-1,2(1,6)-dihydropyridine-3-carbonitriles: UV, NMR and quantum chemical study. in Spectrochimica Acta Part A-Molecular and Biomolecular Spectroscopy, 150, 575-585.
https://doi.org/10.1016/j.saa.2015.05.055
conv_1172

Ajaj I, Markovski J, Rančić M, Mijin D, Milcić M, Jovanović M, Marinković A. Solvent and structural effects in tautomeric 2(6)-hydroxy-4-methyl-6(2)-oxo-1-(substituted phenyl)-1,2(1,6)-dihydropyridine-3-carbonitriles: UV, NMR and quantum chemical study. in Spectrochimica Acta Part A-Molecular and Biomolecular Spectroscopy. 2015;150:575-585.
doi:10.1016/j.saa.2015.05.055
conv_1172 .

Ajaj, Ismail, Markovski, Jasmina, Rančić, Milica, Mijin, Dusan, Milcić, Miloš, Jovanović, Maja, Marinković, Aleksandar, "Solvent and structural effects in tautomeric 2(6)-hydroxy-4-methyl-6(2)-oxo-1-(substituted phenyl)-1,2(1,6)-dihydropyridine-3-carbonitriles: UV, NMR and quantum chemical study" in Spectrochimica Acta Part A-Molecular and Biomolecular Spectroscopy, 150 (2015):575-585,
https://doi.org/10.1016/j.saa.2015.05.055 .,
conv_1172 .

TY  - JOUR
AU  - Rančić, Milica
AU  - Trisović, Nemanja
AU  - Milcić, Miloš
AU  - Jovanović, Maja
AU  - Jovanović, Bratislav
AU  - Marinković, Aleksandar
PY  - 2014
UR  - https://omorika.sfb.bg.ac.rs/handle/123456789/577
AB  - Two series of 4-substituted N-[1-(pyridine-3- and -4-yl)ethylidene]anilines have been synthesized using different methods of conventional and microwave-assisted synthesis, and linear free-energy relationships have been applied to the C-13 NMR chemical shifts of the carbon atoms of interest. The substituent-induced chemical shifts have been analyzed using single substituent parameter and dual substituent parameter methods. The presented correlations describe satisfactorily the field and resonance substituent effects having similar contributions for C1 and the azomethine carbon, with exception of the carbon atom in para position to the substituent X. In both series, negative values have been found for C1 atom (reverse substituent effect). Quantum chemical calculations of the optimized geometries at MP2/6-31G++(d,p) level, together with C-13 NMR chemical shifts, give a better insight into the influence of the molecular conformation on the transmission of electronic substituent effects. The comparison of correlation results for different series of imines with phenyl, 4-nitrophenyl, 2-pyridyl, 3-pyridyl, 4-pyridyl group attached at the azomethine carbon with the results for 4-substituted N-[1-(pyridine-3- and -4-yl)ethylidene]anilines for the same substituent set (X) indicates that a combination of the influences of electronic effects of the substituent X and the (1)-unit can be described as a sensitive balance of different resonance structures.
T2  - Journal of Heterocyclic Chemistry
T1  - Linear Free-Energy Relationships Applied to the 13 C NMR Chemical Shifts in 4-Substituted N -[1-(Pyridine-3-and-4-yl)ethylidene]anilines
EP  - 1451
IS  - 5
SP  - 1442
VL  - 51
DO  - 10.1002/jhet.1752
UR  - conv_1130
ER  - 

@article{
author = "Rančić, Milica and Trisović, Nemanja and Milcić, Miloš and Jovanović, Maja and Jovanović, Bratislav and Marinković, Aleksandar",
year = "2014",
abstract = "Two series of 4-substituted N-[1-(pyridine-3- and -4-yl)ethylidene]anilines have been synthesized using different methods of conventional and microwave-assisted synthesis, and linear free-energy relationships have been applied to the C-13 NMR chemical shifts of the carbon atoms of interest. The substituent-induced chemical shifts have been analyzed using single substituent parameter and dual substituent parameter methods. The presented correlations describe satisfactorily the field and resonance substituent effects having similar contributions for C1 and the azomethine carbon, with exception of the carbon atom in para position to the substituent X. In both series, negative values have been found for C1 atom (reverse substituent effect). Quantum chemical calculations of the optimized geometries at MP2/6-31G++(d,p) level, together with C-13 NMR chemical shifts, give a better insight into the influence of the molecular conformation on the transmission of electronic substituent effects. The comparison of correlation results for different series of imines with phenyl, 4-nitrophenyl, 2-pyridyl, 3-pyridyl, 4-pyridyl group attached at the azomethine carbon with the results for 4-substituted N-[1-(pyridine-3- and -4-yl)ethylidene]anilines for the same substituent set (X) indicates that a combination of the influences of electronic effects of the substituent X and the (1)-unit can be described as a sensitive balance of different resonance structures.",
journal = "Journal of Heterocyclic Chemistry",
title = "Linear Free-Energy Relationships Applied to the 13 C NMR Chemical Shifts in 4-Substituted N -[1-(Pyridine-3-and-4-yl)ethylidene]anilines",
pages = "1451-1442",
number = "5",
volume = "51",
doi = "10.1002/jhet.1752",
url = "conv_1130"
}

Rančić, M., Trisović, N., Milcić, M., Jovanović, M., Jovanović, B.,& Marinković, A.. (2014). Linear Free-Energy Relationships Applied to the 13 C NMR Chemical Shifts in 4-Substituted N -[1-(Pyridine-3-and-4-yl)ethylidene]anilines. in Journal of Heterocyclic Chemistry, 51(5), 1442-1451.
https://doi.org/10.1002/jhet.1752
conv_1130

Rančić M, Trisović N, Milcić M, Jovanović M, Jovanović B, Marinković A. Linear Free-Energy Relationships Applied to the 13 C NMR Chemical Shifts in 4-Substituted N -[1-(Pyridine-3-and-4-yl)ethylidene]anilines. in Journal of Heterocyclic Chemistry. 2014;51(5):1442-1451.
doi:10.1002/jhet.1752
conv_1130 .

Rančić, Milica, Trisović, Nemanja, Milcić, Miloš, Jovanović, Maja, Jovanović, Bratislav, Marinković, Aleksandar, "Linear Free-Energy Relationships Applied to the 13 C NMR Chemical Shifts in 4-Substituted N -[1-(Pyridine-3-and-4-yl)ethylidene]anilines" in Journal of Heterocyclic Chemistry, 51, no. 5 (2014):1442-1451,
https://doi.org/10.1002/jhet.1752 .,
conv_1130 .