Investigation of molecular structure and solvent/temperature effect on tautomerism in (E)-4,6-dibromo-3-methoxy-2-[(p-tolylimino)methyl] phenol, a new thermochromic Schiff base, by using XRD, FT-IR, UV-vis, NMR and DFT methods

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dc.authoridAlbayrak kastas, Cigdem/0000-0003-0235-7460
dc.authoridKastas, Gokhan/0000-0002-5956-405X
dc.contributor.authorKastas, Gokhan
dc.contributor.authorKastas, Cigdem Albayrak
dc.contributor.authorTabak, Ahmet
dc.date.accessioned2025-03-23T19:37:57Z
dc.date.available2025-03-23T19:37:57Z
dc.date.issued2019
dc.departmentSinop Üniversitesi
dc.description.abstractThe molecular structure and the solvent temperature effect on the tautomerism in a new Schiff base, (E)-4,6-clibromo-3-methoxy-2-[(p-tolylimino)methyllphenol, were investigated using spectroscopic (NMR, UV-vis, FT-1R), crystallographic (XRD), computational (DFT and TD-DET) methods and harmonic oscillator model of aromaticity (HOMA). The XRD, DFT and MIR results show that the compound exists in the phenol-imine form in the solid state. HOMA indices support the aromatic structure of the compound. DFT calculations were performed to understand proton transfer process and relatively close values were obtained for the energies of tautomers. UV-vis studies prove the solvent dependence of the tautomerism in the compound by revealing the existence of both phenol-imine and keto-amine forms in polar solvents and only the phenol-imine form in apolar solvent. The TD-DFT results for the electronic transitions lead to the same conclusion as the absorption spectra. H-1 NMR and C-13 NMR studies at room and low (-60 degrees C) temperatures indicate that the tautomeric equilibrium occurs rapidly in the compound. Therefore, it is difficult to observe two tautomers. However, the presence of tautomeric structures is clearly seen in acetone d(6), alternatively underlying the solvent and temperature dependence of tautomerism in the title compound. (C) 2019 Elsevier B.V. All lights reserved.
dc.description.sponsorshipSinop University Scientific Research Coordination Unit [FEF-1901-18-14]
dc.description.sponsorshipThis work was supported by Sinop University Scientific Research Coordination Unit. Project Number: FEF-1901-18-14, 2018. The authors acknowledge to Scientific and Technological Research Application and Research Center, Sinop University, Turkey, for the use of the Bruker D8 QUEST diffractometer.
dc.identifier.doi10.1016/j.saa.2019.117198
dc.identifier.issn1386-1425
dc.identifier.issn1873-3557
dc.identifier.pmid31181503
dc.identifier.scopus2-s2.0-85066859977
dc.identifier.scopusqualityQ1
dc.identifier.urihttps://doi.org/10.1016/j.saa.2019.117198
dc.identifier.urihttps://hdl.handle.net/11486/6055
dc.identifier.volume222
dc.identifier.wosWOS:000482215100035
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.subjectTautomerism
dc.subjectSolvent effect
dc.subjectTemperature effect
dc.subjectThermochromism
dc.subjectSpectroscopy
dc.subjectComputational methods
dc.titleInvestigation of molecular structure and solvent/temperature effect on tautomerism in (E)-4,6-dibromo-3-methoxy-2-[(p-tolylimino)methyl] phenol, a new thermochromic Schiff base, by using XRD, FT-IR, UV-vis, NMR and DFT methods
dc.typeArticle

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