Solvent and structural effects in tautomeric 3-cyano-4-(substituted phenyl)-6-phenyl-2(1H)-pyridones: experimental and quantum chemical study
Samo za registrovane korisnike
2014
Autori
Ajaj, IsmailMarkovski, Jasmina
Marković, Jelena
Jovanović, Maja
Milčić, Miloš
Assaleh, Fathi H.
Marinković, Aleksandar
Članak u časopisu (Objavljena verzija)
Metapodaci
Prikaz svih podataka o dokumentuApstrakt
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.
Ključne reči:
Tautomerism / Solvent effects / Substituent effects / UV-Vis absorption spectroscopy / DFTIzvor:
Structural Chemistry, 2014, 25, 4, 1257-1270Izdavač:
- Springer/Plenum Publishers, New York
Finansiranje / projekti:
- Proučavanje sinteze, strukture i aktivnosti organskih jedinjenja prirodnog i sintetskog porekla (RS-172013)
DOI: 10.1007/s11224-014-0401-y
ISSN: 1040-0400
WoS: 000339391300025
Scopus: 2-s2.0-84905592841
Institucija/grupa
Tehnološko-metalurški fakultetTY - JOUR AU - Ajaj, Ismail AU - Markovski, Jasmina AU - Marković, Jelena AU - Jovanović, Maja AU - Milčić, Miloš AU - Assaleh, Fathi H. AU - Marinković, Aleksandar PY - 2014 UR - http://TechnoRep.tmf.bg.ac.rs/handle/123456789/2790 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 EP - 1270 IS - 4 SP - 1257 VL - 25 DO - 10.1007/s11224-014-0401-y ER -
@article{ author = "Ajaj, Ismail and Markovski, Jasmina and Marković, Jelena and Jovanović, Maja and Milčić, Miloš and Assaleh, Fathi H. 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", pages = "1270-1257", number = "4", volume = "25", doi = "10.1007/s11224-014-0401-y" }
Ajaj, I., Markovski, J., Marković, J., Jovanović, M., Milčić, M., Assaleh, F. H.,& 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 I, Markovski J, Marković J, Jovanović M, Milčić M, Assaleh FH, 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, Markovski, Jasmina, Marković, Jelena, Jovanović, Maja, Milčić, Miloš, Assaleh, Fathi H., 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 . .