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
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Ajaj, IsmailMarkovski, Jasmina S.
Rancic, Milica
Mijin, Dušan Ž.
Milčić, Miloš K.
Jovanović, Maja
Marinković, Aleksandar D.
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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. Baders 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. (C) 2015 Elsevier B....V. All rights reserved.
Keywords:
Tautomerism / Solvent effects / Substituent effects / DFT / Derivative spectroscopySource:
Spectrochimica Acta. Part A: Molecular and Biomolecular Spectroscopy, 2015, 150, 575-585Funding / projects:
- Study of the Synthesis, Structure and Activity of Natural and Synthetic Organic Compounds (RS-MESTD-Basic Research (BR or ON)-172013)
DOI: 10.1016/j.saa.2015.05.055
ISSN: 1386-1425
PubMed: 26079514
WoS: 000361774900067
Scopus: 2-s2.0-84930960369
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VinčaTY - JOUR AU - Ajaj, Ismail AU - Markovski, Jasmina S. AU - Rancic, Milica AU - Mijin, Dušan Ž. AU - Milčić, Miloš K. AU - Jovanović, Maja AU - Marinković, Aleksandar D. PY - 2015 UR - https://vinar.vin.bg.ac.rs/handle/123456789/746 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. Baders 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. (C) 2015 Elsevier B.V. All rights reserved. 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 VL - 150 SP - 575 EP - 585 DO - 10.1016/j.saa.2015.05.055 ER -
@article{ author = "Ajaj, Ismail and Markovski, Jasmina S. and Rancic, Milica and Mijin, Dušan Ž. and Milčić, Miloš K. and Jovanović, Maja and Marinković, Aleksandar D.", 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. Baders 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. (C) 2015 Elsevier B.V. All rights reserved.", 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", volume = "150", pages = "575-585", doi = "10.1016/j.saa.2015.05.055" }
Ajaj, I., Markovski, J. S., Rancic, M., Mijin, D. Ž., Milčić, M. K., Jovanović, M.,& Marinković, A. D.. (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
Ajaj I, Markovski JS, Rancic M, Mijin DŽ, Milčić MK, Jovanović M, Marinković AD. 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 .
Ajaj, Ismail, Markovski, Jasmina S., Rancic, Milica, Mijin, Dušan Ž., Milčić, Miloš K., Jovanović, Maja, Marinković, Aleksandar D., "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 . .