Molecular structure of (Z)-6-[(5-chloro-2-hydroxyphenylamino) methylene]-3-(diethylamino)cyclohexa-2,4-dienone: A combined experimental and theoretical study

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dc.authoridAlbayrak kastas, Cigdem/0000-0003-0235-7460
dc.contributor.authorKosar, Basak
dc.contributor.authorAlbayrak, Cigdem
dc.contributor.authorOdabasoglu, Mustafa
dc.contributor.authorBuyukgungor, Orhan
dc.date.accessioned2025-03-23T19:40:50Z
dc.date.available2025-03-23T19:40:50Z
dc.date.issued2011
dc.departmentSinop Üniversitesi
dc.description.abstractThe crystal structure and spectroscopic properties of ortho-hydroxy Schiff base compound (Z)-6-[(5-chloro-2-hydroxyphenylamino)methylene]-3-(diethylamino)cyclohexa-2,4-dienone were determined by X-ray diffraction, IR and UV-Vis spectroscopy techniques. Molecules of the compound exist as NH tautomeric form in solid state. The gas phase geometry optimizations of two possible tautomeric forms of the title compound were achieved using OFT calculations at B3LYP/6-31G(d,p) level of theory. In order to describe the potential energy barrier belonging to the intramolecular proton transfer and to observe the effects of transfer on the molecular geometry, a relaxed potential energy surface (PES) scan was performed based on the optimized geometry of the NH tautomeric form by varying the redundant internal coordinate, N-H bond distance. At the same level of theory, the vibrational frequencies were calculated and compared with the experimental frequencies. The electronic absorption spectra of the tautomers were calculated using time-dependent density functional theory (TO-OFT) method started from solution phase optimized geometries and compared with the experimental ones. Crown Copyright (c) 2010 Published by Elsevier B.V. All rights reserved.
dc.identifier.doi10.1016/j.molstruc.2010.12.031
dc.identifier.endpage37
dc.identifier.issn0022-2860
dc.identifier.issn1872-8014
dc.identifier.issue1-3
dc.identifier.scopus2-s2.0-79952191055
dc.identifier.scopusqualityQ1
dc.identifier.startpage31
dc.identifier.urihttps://doi.org/10.1016/j.molstruc.2010.12.031
dc.identifier.urihttps://hdl.handle.net/11486/6428
dc.identifier.volume989
dc.identifier.wosWOS:000288832800004
dc.identifier.wosqualityQ2
dc.indekslendigikaynakWeb of Science
dc.indekslendigikaynakScopus
dc.language.isoen
dc.publisherElsevier
dc.relation.ispartofJournal of Molecular Structure
dc.relation.publicationcategoryMakale - Uluslararası Hakemli Dergi - Kurum Öğretim Elemanı
dc.rightsinfo:eu-repo/semantics/closedAccess
dc.snmzKA_WOS_20250323
dc.subjectSchiff base
dc.subjectTautomerism
dc.subjectIntramolecular proton transfer
dc.subjectHOMA
dc.subjectDFT
dc.titleMolecular structure of (Z)-6-[(5-chloro-2-hydroxyphenylamino) methylene]-3-(diethylamino)cyclohexa-2,4-dienone: A combined experimental and theoretical study
dc.typeArticle

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