Experimental and molecular modeling investigation of (E)-N-{2-[(2-hydroxybenzylidene)amino]phenyl}benzenesulfonamide

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dc.authoriddayan, serkan/0000-0003-4171-7297
dc.authoriddayan, osman/0000-0002-0764-1965
dc.authoridOzdemir, Namik/0000-0003-3371-9874
dc.contributor.authorOzdemir, Namik
dc.contributor.authorDayan, Serkan
dc.contributor.authorDayan, Osman
dc.contributor.authorDincer, Muharrem
dc.contributor.authorKalaycioglu, Nilgun O.
dc.date.accessioned2025-01-27T20:39:23Z
dc.date.available2025-01-27T20:39:23Z
dc.date.issued2013
dc.departmentÇanakkale Onsekiz Mart Üniversitesi
dc.description.abstractThe Schiff base compound (E)-N-{2-[(2-hydroxybenzylidene)amino]phenyl}benzenesulfonamide has been synthesized and characterized by IR, NMR and Uv-vis spectroscopies, and single-crystal X-ray diffraction technique. In addition, quantum chemical calculations employing density functional theory (DFT) method with the 6311++G(d,p) basis set were performed to study the molecular, spectroscopic and some electronic structure properties of the title compound, and the results were compared with the experimental findings. There exists a good correlation between experimental and theoretical data. Enol-imine/keto-amine tautomerization mechanism was investigated in the gas phase and in solution phase using the polarizable continuum model (PCM) approximation. The energetic and thermodynamic parameters of the enol-imineketo-amine transfer process show that the single proton exchange is thermodynamically unfavored both in the gas phase and in solution phase. However, the reverse reaction seems to be feasible with a low barrier height and is supported by negative values in enthalpy and free energy changes both in the gas phase and in solution phase. The solvent effect is found to be sizable with increasing polarity of the solvents for the reverse reaction. The predicted nonlinear optical properties of the compound are found to be much greater than those of urea.
dc.description.sponsorshipUniversity Research Fund [F-279]; Erciyes University (ERUBAP) [FBA-11-3547, 3547]
dc.description.sponsorshipWe wish to thank Professor Dr Orhan Buyukgungor for his help with the data collection and the Faculty of Arts and Sciences, Ondokuz Mayis University, Turkey, for the use of the STOE IPDS II diffractometer (purchased under grant No. F-279 of the University Research Fund). We further acknowledge the financial support granted by Erciyes University (ERUBAP), (FBA-11-3547, ID: 3547)
dc.identifier.doi10.1080/00268976.2012.742209
dc.identifier.endpage723
dc.identifier.issn0026-8976
dc.identifier.issn1362-3028
dc.identifier.issue6
dc.identifier.scopus2-s2.0-84962439375
dc.identifier.scopusqualityQ2
dc.identifier.startpage707
dc.identifier.urihttps://doi.org/10.1080/00268976.2012.742209
dc.identifier.urihttps://hdl.handle.net/20.500.12428/23934
dc.identifier.volume111
dc.identifier.wosWOS:000318351700001
dc.identifier.wosqualityQ3
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.subjectIR
dc.subjectNMR and Uv-vis spectroscopy
dc.subjectdensity functional theory
dc.subjectenol-imine
dc.subjectketo-amine tautomerism
dc.subjectsolvent effects
dc.titleExperimental and molecular modeling investigation of (E)-N-{2-[(2-hydroxybenzylidene)amino]phenyl}benzenesulfonamide
dc.typeArticle

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