Solvent and structural effects in tautomeric 3-cyano-4-(substituted phenyl)-6-phenyl-2(1H)-pyridones: experimental and quantum chemical study
Нема приказа
Аутори
Ajaj, IsmailMarkovski, Jasmina S.
Markovic, Jelena
Jovanović, Maja
Milčić, Miloš K.
Assaleh, Fathi
Marinković, Aleksandar D.
Чланак у часопису
Метаподаци
Приказ свих података о документуАпстракт
The tautomeric equilibria between 2-pyridone and 2-hydroxypyridine forms of methoxy, chloro, and nitro derivatives of 3-cyano-4-(2-, 3-, and 4-substituted phenyl)-6-phenyl-2(1H)-pyridones were evaluated from UV/Vis spectral data. Linear solvation energy relationships of Kamlet-Taft and Catalan-rationalized solvent have influence on tautomeric equilibria. Transmission of substituent effect was analyzed by the Hammett equation. Quantum chemical calculations were performed by density functional theory (B3LYP). The experimental data were interpreted with the aid of time-dependent density functional method. Electron density distribution was analyzed by Baders analysis. It was found that substituents of different electronic properties change the extent of conjugation, and affect intramolecular charge transfer character. Theoretical calculations and experimental results gave insight into the influence of the molecular conformation on the transmission of substituent effects, as well as on cont...ribution of different solvent-solute interactions.
Кључне речи:
Tautomerism / Solvent effects / Substituent effects / UV-Vis absorption spectroscopy / DFTИзвор:
Structural Chemistry, 2014, 25, 4, 1257-1270Финансирање / пројекти:
- Проучавање синтезе, структуре и активности органских једињења природног и синтетског порекла (RS-MESTD-Basic Research (BR or ON)-172013)
DOI: 10.1007/s11224-014-0401-y
ISSN: 1040-0400; 1572-9001
WoS: 000339391300025
Scopus: 2-s2.0-84905592841
Колекције
Институција/група
VinčaTY - JOUR AU - Ajaj, Ismail AU - Markovski, Jasmina S. AU - Markovic, Jelena AU - Jovanović, Maja AU - Milčić, Miloš K. AU - Assaleh, Fathi AU - Marinković, Aleksandar D. PY - 2014 UR - https://vinar.vin.bg.ac.rs/handle/123456789/5453 AB - The tautomeric equilibria between 2-pyridone and 2-hydroxypyridine forms of methoxy, chloro, and nitro derivatives of 3-cyano-4-(2-, 3-, and 4-substituted phenyl)-6-phenyl-2(1H)-pyridones were evaluated from UV/Vis spectral data. Linear solvation energy relationships of Kamlet-Taft and Catalan-rationalized solvent have influence on tautomeric equilibria. Transmission of substituent effect was analyzed by the Hammett equation. Quantum chemical calculations were performed by density functional theory (B3LYP). The experimental data were interpreted with the aid of time-dependent density functional method. Electron density distribution was analyzed by Baders analysis. It was found that substituents of different electronic properties change the extent of conjugation, and affect intramolecular charge transfer character. Theoretical calculations and experimental results gave insight into the influence of the molecular conformation on the transmission of substituent effects, as well as on contribution of different solvent-solute interactions. T2 - Structural Chemistry T1 - Solvent and structural effects in tautomeric 3-cyano-4-(substituted phenyl)-6-phenyl-2(1H)-pyridones: experimental and quantum chemical study VL - 25 IS - 4 SP - 1257 EP - 1270 DO - 10.1007/s11224-014-0401-y ER -
@article{ author = "Ajaj, Ismail and Markovski, Jasmina S. and Markovic, Jelena and Jovanović, Maja and Milčić, Miloš K. and Assaleh, Fathi and Marinković, Aleksandar D.", year = "2014", abstract = "The tautomeric equilibria between 2-pyridone and 2-hydroxypyridine forms of methoxy, chloro, and nitro derivatives of 3-cyano-4-(2-, 3-, and 4-substituted phenyl)-6-phenyl-2(1H)-pyridones were evaluated from UV/Vis spectral data. Linear solvation energy relationships of Kamlet-Taft and Catalan-rationalized solvent have influence on tautomeric equilibria. Transmission of substituent effect was analyzed by the Hammett equation. Quantum chemical calculations were performed by density functional theory (B3LYP). The experimental data were interpreted with the aid of time-dependent density functional method. Electron density distribution was analyzed by Baders analysis. It was found that substituents of different electronic properties change the extent of conjugation, and affect intramolecular charge transfer character. Theoretical calculations and experimental results gave insight into the influence of the molecular conformation on the transmission of substituent effects, as well as on contribution of different solvent-solute interactions.", journal = "Structural Chemistry", title = "Solvent and structural effects in tautomeric 3-cyano-4-(substituted phenyl)-6-phenyl-2(1H)-pyridones: experimental and quantum chemical study", volume = "25", number = "4", pages = "1257-1270", doi = "10.1007/s11224-014-0401-y" }
Ajaj, I., Markovski, J. S., Markovic, J., Jovanović, M., Milčić, M. K., Assaleh, F.,& Marinković, A. D.. (2014). Solvent and structural effects in tautomeric 3-cyano-4-(substituted phenyl)-6-phenyl-2(1H)-pyridones: experimental and quantum chemical study. in Structural Chemistry, 25(4), 1257-1270. https://doi.org/10.1007/s11224-014-0401-y
Ajaj I, Markovski JS, Markovic J, Jovanović M, Milčić MK, Assaleh F, Marinković AD. Solvent and structural effects in tautomeric 3-cyano-4-(substituted phenyl)-6-phenyl-2(1H)-pyridones: experimental and quantum chemical study. in Structural Chemistry. 2014;25(4):1257-1270. doi:10.1007/s11224-014-0401-y .
Ajaj, Ismail, Markovski, Jasmina S., Markovic, Jelena, Jovanović, Maja, Milčić, Miloš K., Assaleh, Fathi, Marinković, Aleksandar D., "Solvent and structural effects in tautomeric 3-cyano-4-(substituted phenyl)-6-phenyl-2(1H)-pyridones: experimental and quantum chemical study" in Structural Chemistry, 25, no. 4 (2014):1257-1270, https://doi.org/10.1007/s11224-014-0401-y . .