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dc.creatorAjaj, Ismail
dc.creatorMarkovski, Jasmina
dc.creatorMarković, Jelena
dc.creatorJovanović, Maja
dc.creatorMilčić, Miloš
dc.creatorAssaleh, Fathi H.
dc.creatorMarinković, Aleksandar
dc.date.accessioned2021-03-10T12:32:15Z
dc.date.available2021-03-10T12:32:15Z
dc.date.issued2014
dc.identifier.issn1040-0400
dc.identifier.urihttp://TechnoRep.tmf.bg.ac.rs/handle/123456789/2790
dc.description.abstractThe 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.en
dc.publisherSpringer/Plenum Publishers, New York
dc.relationinfo:eu-repo/grantAgreement/MESTD/Basic Research (BR or ON)/172013/RS//
dc.rightsrestrictedAccess
dc.sourceStructural Chemistry
dc.subjectTautomerismen
dc.subjectSolvent effectsen
dc.subjectSubstituent effectsen
dc.subjectUV-Vis absorption spectroscopyen
dc.subjectDFTen
dc.titleSolvent and structural effects in tautomeric 3-cyano-4-(substituted phenyl)-6-phenyl-2(1H)-pyridones: experimental and quantum chemical studyen
dc.typearticle
dc.rights.licenseARR
dc.citation.epage1270
dc.citation.issue4
dc.citation.other25(4): 1257-1270
dc.citation.rankM22
dc.citation.spage1257
dc.citation.volume25
dc.identifier.doi10.1007/s11224-014-0401-y
dc.identifier.rcubconv_4321
dc.identifier.scopus2-s2.0-84905592841
dc.identifier.wos000339391300025
dc.type.versionpublishedVersion


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