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dc.contributor.authorÖzdemir, Namık
dc.contributor.authorTurkpence, Deniz
dc.date.accessioned2020-06-21T14:04:16Z
dc.date.available2020-06-21T14:04:16Z
dc.date.issued2013
dc.identifier.issn2210-271X
dc.identifier.issn1872-7999
dc.identifier.urihttps://doi.org/10.1016/j.comptc.2013.10.001
dc.identifier.urihttps://hdl.handle.net/20.500.12712/15585
dc.descriptionOzdemir, Namik/0000-0003-3371-9874; Turkpence, Deniz/0000-0002-5182-374Xen_US
dc.descriptionWOS: 000327806100006en_US
dc.description.abstractThe thione-thiol tautomerism and intermolecular double proton transfer reaction for the title triazole compound were studied at the B3LYP level of theory using 6-311++G(d,p) basis function. The solvent effect on the proton transfer reactions was investigated in three solvents (chloroform, methanol and water) using the polarizable continuum model (PCM) approximation (direct solvent effect) and solvent-assisted mechanism. The results show that the thione-enol tautomer is the most stable isomer among the four possible tautomeric forms of the compound both in the gas phase and in solution phase. A very high tautomeric energy barrier is found for the thione-thiol tautomerism between the enol and keto forms of the compound both in the gas phase and in solution phase, indicating a quite disfavored process. The direct solvent effect is found to be sizable with increasing polarity of the solvents. Even though the presence of the solvent molecules significantly lowers the barrier of the proton transfer, it is not adequate for the reaction to occur. The energetic and thermodynamic parameters of the double proton transfer process show that the double proton exchange from thione-enol dimer to thiol-enol dimer is thermodynamically unfavored. However, the exchange from thiol-enol dimer to thione-enol dimer for the gas phase and methanol phase seems to be feasible with a low barrier height, and is supported by negative values in enthalpy and free energy changes. The intermolecular hydrogen bonding interactions were analyzed in the gas phase regarding their geometries and energies. The stability of the H-bonds comes in the order of O1-H1 center dot center dot center dot N1 > S1 H2 center dot center dot center dot N2 > N2-H2 center dot center dot center dot S1 > N2-H2 center dot center dot center dot N1. (C) 2013 Elsevier B.V. All rights reserved.en_US
dc.language.isoengen_US
dc.publisherElsevieren_US
dc.relation.isversionof10.1016/j.comptc.2013.10.001en_US
dc.rightsinfo:eu-repo/semantics/closedAccessen_US
dc.subjectThione-thiol tautomerismen_US
dc.subjectDouble proton transfer reactionen_US
dc.subjectSolvent effecten_US
dc.subjectHydrogen bondingen_US
dc.subjectDFTen_US
dc.titleTheoretical investigation of thione-thiol tautomerism, intermolecular double proton transfer reaction and hydrogen bonding interactions in 4-ethyl-5-(2-hydroxyphenyl)-2H-1,2,4-triazole-3(4H)-thioneen_US
dc.typearticleen_US
dc.contributor.departmentOMÜen_US
dc.identifier.volume1025en_US
dc.identifier.startpage35en_US
dc.identifier.endpage45en_US
dc.relation.journalComputational and Theoretical Chemistryen_US
dc.relation.publicationcategoryMakale - Uluslararası Hakemli Dergi - Kurum Öğretim Elemanıen_US


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