Investigation of enol-imine/keto-amine tautomerism in (E)-4-[(2-hydroxybenzylidene)amino]phenyl benzenesulphonate by experimental and molecular modelling methods

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dc.authoridOzdemir, Namik/0000-0003-3371-9874
dc.authoriddayan, osman/0000-0002-0764-1965
dc.contributor.authorOzdemir, Namik
dc.contributor.authorKagit, Reyhan
dc.contributor.authorDayan, Osman
dc.date.accessioned2025-01-27T20:59:42Z
dc.date.available2025-01-27T20:59:42Z
dc.date.issued2016
dc.departmentÇanakkale Onsekiz Mart Üniversitesi
dc.description.abstractThe Schiff base compound (E)-4-[(2-hydroxybenzylidene)amino]phenyl benzenesulphonate has been synthesised from the reaction of 4-aminophenyl benzenesulphonate and salicylaldehyde, and characterised by spectroscopic and single-crystal X-ray diffraction techniques. Quantum chemical calculations employing density functional theory method with the 6-311++G(d,p) basis set were performed to study the molecular, spectroscopic and enol-imine/keto-amine tautomerisation mechanism of the title compound. An acceptable correlation between experimental and theoretical findings is obtained. Enol-imine/keto-amine tautomerisation mechanism was investigated in the gas phase and in solution phase using the polarisable continuum model approximation. The energetic and thermodynamic parameters of the enol-imine -> keto-amine transfer process show that the single proton exchange is unfavoured in all cases. Contrarily, the reverse reaction seems to be feasible with a very low barrier height and is supported by negative values in enthalpy and free energy changes for all cases.
dc.description.sponsorshipCanakkale Onsekiz Mart University Scientific Research Projects Commission [FYL-2014-180]
dc.description.sponsorshipCanakkale Onsekiz Mart University Scientific Research Projects Commission [project number FYL-2014-180].
dc.identifier.doi10.1080/00268976.2015.1116715
dc.identifier.endpage768
dc.identifier.issn0026-8976
dc.identifier.issn1362-3028
dc.identifier.issue6
dc.identifier.scopus2-s2.0-84949811435
dc.identifier.scopusqualityQ2
dc.identifier.startpage757
dc.identifier.urihttps://doi.org/10.1080/00268976.2015.1116715
dc.identifier.urihttps://hdl.handle.net/20.500.12428/26796
dc.identifier.volume114
dc.identifier.wosWOS:000372129500002
dc.identifier.wosqualityQ2
dc.indekslendigikaynakWeb of Science
dc.indekslendigikaynakScopus
dc.language.isoen
dc.publisherTaylor & Francis Ltd
dc.relation.ispartofMolecular Physics
dc.relation.publicationcategoryinfo:eu-repo/semantics/openAccess
dc.rightsinfo:eu-repo/semantics/closedAccess
dc.snmzKA_WoS_20250125
dc.subjectCrystal structure
dc.subjectsolvent effects
dc.subjectdensity functional theory
dc.subjectspectroscopy
dc.subjectenol-imine/keto-amine tautomerism
dc.titleInvestigation of enol-imine/keto-amine tautomerism in (E)-4-[(2-hydroxybenzylidene)amino]phenyl benzenesulphonate by experimental and molecular modelling methods
dc.typeArticle

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