Survey of conformational isomerism in (E)-2-[(4-bromophenolimino)methyl]-5-(diethylamino)phenol compound from structural and thermochemical points of view

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dc.authoridAlbayrak kastas, Cigdem/0000-0003-0235-7460
dc.contributor.authorAlbayrak, Cigdem
dc.contributor.authorKastas, Gokhan
dc.contributor.authorOdabasoglu, Mustafa
dc.contributor.authorFrank, Rene
dc.date.accessioned2025-03-23T19:38:08Z
dc.date.available2025-03-23T19:38:08Z
dc.date.issued2012
dc.departmentSinop Üniversitesi
dc.description.abstractIn this study, (E)-2[(4-bromophenylimino)methyl]-5-(diethylamino)phenol compound was investigated by mainly focusing on conformational isomerism. For this purpose, molecular structure and spectroscopic properties of the compound were experimentally characterized by X-ray diffraction, FT-IR and UV-Vis spectroscopic techniques, and computationally by DFT method. The X-ray diffraction analysis of the compound shows the formation of two conformers (anti and eclipsed) related to the ethyl groups of the compound. The two conformers are connected to each other by non-covalent C-H center dot center dot center dot Br and C-H center dot center dot center dot pi interactions. The combination of these interactions is resulted in fused R-2(2)(10) and R-2(4)(20) synthons which are responsible for the tape structure of crystal packing arrangement. The X-ray diffraction and FT-IR analyses also reveal the existence of enol form in the solid state. From thermochemical point of view, the computational investigation of isomerism includes three studies: the calculation of (a) the rate constants for transmission from anti or eclipsed conformations to transition state by using Eyring equation, (b) the activation energy needed for isomerism by using Arrhenius equation, (c) the equilibrium constant from anti conformer to eclipsed conformer by using the equation including the change in Gibbs free energy. The dependence of tautomerism on solvent types was studied on the basis of UV-Vis spectra recorded in different organic solvents. The results showed that the compound exists in enol form in all solvents except ethyl alcohol. (C) 2012 Elsevier B.V. All rights reserved.
dc.identifier.doi10.1016/j.saa.2012.04.074
dc.identifier.endpage669
dc.identifier.issn1386-1425
dc.identifier.pmid22591794
dc.identifier.scopus2-s2.0-84862212659
dc.identifier.scopusqualityQ1
dc.identifier.startpage664
dc.identifier.urihttps://doi.org/10.1016/j.saa.2012.04.074
dc.identifier.urihttps://hdl.handle.net/11486/6071
dc.identifier.volume95
dc.identifier.wosWOS:000306304800088
dc.identifier.wosqualityQ1
dc.indekslendigikaynakWeb of Science
dc.indekslendigikaynakScopus
dc.indekslendigikaynakPubMed
dc.language.isoen
dc.publisherPergamon-Elsevier Science Ltd
dc.relation.ispartofSpectrochimica Acta Part A-Molecular and Biomolecular Spectroscopy
dc.relation.publicationcategoryMakale - Uluslararası Hakemli Dergi - Kurum Öğretim Elemanı
dc.rightsinfo:eu-repo/semantics/closedAccess
dc.snmzKA_WOS_20250323
dc.subjectSchiff base
dc.subjectIntramolecular hydrogen bond
dc.subjectDFT
dc.subjectConformational analysis
dc.subjectIsomerism
dc.subjectIR and UV-Vis spectroscopies
dc.titleSurvey of conformational isomerism in (E)-2-[(4-bromophenolimino)methyl]-5-(diethylamino)phenol compound from structural and thermochemical points of view
dc.typeArticle

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