Direct and solvent-assisted thione-thiol tautomerism in 5-(thiophen-2-yl)-1,3,4-oxadiazole-2(3H)-thione: Experimental and molecular modeling study

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dc.authoridKOPARIR, METIN/0000-0003-1031-783X
dc.authoridARSLAN, N. Burcu/0000-0002-1880-1047
dc.authoridKoparir, Pelin/0000-0002-3981-9748
dc.authoridDege, Necmi/0000-0003-0660-4721
dc.authoridOzdemir, Namik/0000-0003-3371-9874
dc.authoriddayan, osman/0000-0002-0764-1965
dc.contributor.authorArslan, N. Burcu
dc.contributor.authorOzdemir, Namik
dc.contributor.authorDayan, Osman
dc.contributor.authorDege, Necmi
dc.contributor.authorKoparir, Metin
dc.contributor.authorKoparir, Pelin
dc.contributor.authorMuglu, Halit
dc.date.accessioned2025-01-27T21:00:02Z
dc.date.available2025-01-27T21:00:02Z
dc.date.issued2014
dc.departmentÇanakkale Onsekiz Mart Üniversitesi
dc.description.abstractThe compound has been synthesized and characterized by IR, NMR and X-ray diffraction. Quantum chemical calculations at B3LYP/6-311++G(d,p) level were performed to study the molecular and spectroscopic properties, conformational equilibrium, thione <-> thiol tautomerism and intermolecular double proton transfer reaction of the compound. The obtained structural and spectroscopic results are well in agreement with the experimental data. The solvent effect on the proton transfer reaction was investigated in three solvents using the polarizable continuum model approximation and solvent-assisted mechanism. The anti-thione tautomer is the most stable isomer among the four possible structural forms both in the gas phase and in solution phase. A high tautomeric energy barrier is found for the tautomerism between the anti and syn forms of the compound, indicating a quite disfavored process. Although the presence of one methanol or water solvent molecule significantly lowers the energy barrier, it is not adequate for the reaction to occur. (C) 2014 Elsevier B.V. All rights reserved.
dc.description.sponsorshipUniversity Research Fund [F-279]
dc.description.sponsorshipWe acknowledge 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 would also like to thank the reviewers for their helpful comments and suggestions to improve the manuscript.
dc.identifier.doi10.1016/j.chemphys.2014.05.006
dc.identifier.endpage11
dc.identifier.issn0301-0104
dc.identifier.issn1873-4421
dc.identifier.scopus2-s2.0-84901944174
dc.identifier.scopusqualityQ2
dc.identifier.startpage1
dc.identifier.urihttps://doi.org/10.1016/j.chemphys.2014.05.006
dc.identifier.urihttps://hdl.handle.net/20.500.12428/26921
dc.identifier.volume439
dc.identifier.wosWOS:000338705600001
dc.identifier.wosqualityQ3
dc.indekslendigikaynakWeb of Science
dc.indekslendigikaynakScopus
dc.language.isoen
dc.publisherElsevier
dc.relation.ispartofChemical Physics
dc.relation.publicationcategoryinfo:eu-repo/semantics/openAccess
dc.rightsinfo:eu-repo/semantics/closedAccess
dc.snmzKA_WoS_20250125
dc.subjectCrystal structure
dc.subjectIR and NMR spectroscopy
dc.subjectDFT
dc.subjectThione-thiol tautomerism
dc.subjectSolvent effect
dc.titleDirect and solvent-assisted thione-thiol tautomerism in 5-(thiophen-2-yl)-1,3,4-oxadiazole-2(3H)-thione: Experimental and molecular modeling study
dc.typeArticle

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