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
Samo za registrovane korisnike
2015
Autori
Ajaj, Ismail A.Markovski, Jasmina
Rančić, Milica
Mijin, Dušan
Milčić, Miloš K.
Jovanović, Maja
Marinković, Aleksandar
Članak u časopisu (Objavljena verzija)
Metapodaci
Prikaz svih podataka o dokumentuApstrakt
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.
Ključne reči:
Tautomerism / Solvent effects / Substituent effects / DFT / Derivative spectroscopyIzvor:
Spectrochimica Acta. Part A: Molecular and Biomolecular Spectroscopy, 2015, 150, 575-585Izdavač:
- Pergamon-Elsevier Science Ltd, Oxford
Finansiranje / projekti:
- Proučavanje sinteze, strukture i aktivnosti organskih jedinjenja prirodnog i sintetskog porekla (RS-MESTD-Basic Research (BR or ON)-172013)
Napomena:
- Supplementary material: http://cherry.chem.bg.ac.rs/handle/123456789/3421
DOI: 10.1016/j.saa.2015.05.055
ISSN: 1386-1425
PubMed: 26079514
WoS: 000361774900067
Scopus: 2-s2.0-84930960369
Kolekcije
Institucija/grupa
Hemijski fakultet / Faculty of ChemistryTY - JOUR AU - Ajaj, Ismail A. AU - Markovski, Jasmina AU - Rančić, Milica AU - Mijin, Dušan AU - Milčić, Miloš K. AU - Jovanović, Maja AU - Marinković, Aleksandar PY - 2015 UR - https://cherry.chem.bg.ac.rs/handle/123456789/1971 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. PB - Pergamon-Elsevier Science Ltd, Oxford 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 A. and Markovski, Jasmina and Rančić, Milica and Mijin, Dušan and Milčić, Miloš K. 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.", publisher = "Pergamon-Elsevier Science Ltd, Oxford", 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. A., Markovski, J., Rančić, M., Mijin, D., Milčić, M. K., 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 Pergamon-Elsevier Science Ltd, Oxford., 150, 575-585. https://doi.org/10.1016/j.saa.2015.05.055
Ajaj IA, Markovski J, Rančić M, Mijin D, Milčić MK, 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 .
Ajaj, Ismail A., Markovski, Jasmina, Rančić, Milica, Mijin, Dušan, Milčić, Miloš K., 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 . .