TechnoRep - Faculty of Technology and Metallurgy Repository
University of Belgrade - Faculty of Technology and Metallurgy
    • English
    • Српски
    • Српски (Serbia)
  • English 
    • English
    • Serbian (Cyrillic)
    • Serbian (Latin)
  • Login
View Item 
  •   TechnoRep
  • Tehnološko-metalurški fakultet
  • Radovi istraživača / Researchers’ publications (TMF)
  • View Item
  •   TechnoRep
  • Tehnološko-metalurški fakultet
  • Radovi istraživača / Researchers’ publications (TMF)
  • View Item
JavaScript is disabled for your browser. Some features of this site may not work without it.

Solvent and structural effects in tautomeric 3-cyano-4-(substituted phenyl)-6-phenyl-2(1H)-pyridones: experimental and quantum chemical study

Authorized Users Only
2014
Authors
Ajaj, Ismail
Markovski, Jasmina
Marković, Jelena
Jovanović, Maja
Milčić, Miloš
Assaleh, Fathi H.
Marinković, Aleksandar
Article (Published version)
Metadata
Show full item record
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 con...tribution of different solvent-solute interactions.

Keywords:
Tautomerism / Solvent effects / Substituent effects / UV-Vis absorption spectroscopy / DFT
Source:
Structural Chemistry, 2014, 25, 4, 1257-1270
Publisher:
  • Springer/Plenum Publishers, New York
Funding / projects:
  • Study of the Synthesis, Structure and Activity of Natural and Synthetic Organic Compounds (RS-172013)

DOI: 10.1007/s11224-014-0401-y

ISSN: 1040-0400

WoS: 000339391300025

Scopus: 2-s2.0-84905592841
[ Google Scholar ]
10
10
URI
http://TechnoRep.tmf.bg.ac.rs/handle/123456789/2790
Collections
  • Radovi istraživača / Researchers’ publications (TMF)
Institution/Community
Tehnološko-metalurški fakultet
TY  - 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
UR  - conv_4321
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",
url = "conv_4321"
}
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
conv_4321
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
conv_4321 .
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 .,
conv_4321 .

DSpace software copyright © 2002-2015  DuraSpace
About TechnoRep | Send Feedback

OpenAIRERCUB
 

 

All of DSpaceInstitutions/communitiesAuthorsTitlesSubjectsThis institutionAuthorsTitlesSubjects

Statistics

View Usage Statistics

DSpace software copyright © 2002-2015  DuraSpace
About TechnoRep | Send Feedback

OpenAIRERCUB