Solvent and structural effects in tautomeric 3-cyano-4-(substituted phenyl)-6-phenyl-2(1H)-pyridones: experimental and quantum chemical study
Само за регистроване кориснике
2014
Аутори
Ajaj, Ismail A.Markovski, Jasmina
Marković, Jelena
Jovanović, Maja
Milčić, Miloš K.
Assaleh, Fathi
Marinković, Aleksandar
Чланак у часопису (Објављена верзија)
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 Bader's 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 con...tribution of different solvent-solute interactions.
Кључне речи:
Tautomerism / Solvent effects / Substituent effects / UV-Vis absorption spectroscopy / DFTИзвор:
Structural Chemistry, 2014, 25, 4, 1257-1270Издавач:
- Springer/Plenum Publishers, New York
Финансирање / 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
WoS: 000339391300025
Scopus: 2-s2.0-84905592841
Колекције
Институција/група
Hemijski fakultet / Faculty of ChemistryTY - JOUR AU - Ajaj, Ismail A. AU - Markovski, Jasmina AU - Marković, Jelena AU - Jovanović, Maja AU - Milčić, Miloš K. AU - Assaleh, Fathi AU - Marinković, Aleksandar PY - 2014 UR - https://cherry.chem.bg.ac.rs/handle/123456789/1817 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 Bader's 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. PB - Springer/Plenum Publishers, New York 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 A. and Markovski, Jasmina and Marković, Jelena and Jovanović, Maja and Milčić, Miloš K. and Assaleh, Fathi and Marinković, Aleksandar", 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 Bader's 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.", publisher = "Springer/Plenum Publishers, New York", 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. A., Markovski, J., Marković, J., Jovanović, M., Milčić, M. K., Assaleh, F.,& Marinković, A.. (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 Springer/Plenum Publishers, New York., 25(4), 1257-1270. https://doi.org/10.1007/s11224-014-0401-y
Ajaj IA, Markovski J, Marković J, Jovanović M, Milčić MK, Assaleh F, Marinković A. 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 A., Markovski, Jasmina, Marković, Jelena, Jovanović, Maja, Milčić, Miloš K., Assaleh, Fathi, Marinković, Aleksandar, "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 . .