Tautomerism in 4-chlorophenyl benzoylcarbamodithioate: Experimental and DFT study

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dc.authoridARSLAN, N. Burcu/0000-0002-1880-1047
dc.authoridOzdemir, Namik/0000-0003-3371-9874
dc.contributor.authorAydin, Fatma
dc.contributor.authorArslan, N. Burcu
dc.contributor.authorOzdemir, Namik
dc.date.accessioned2025-01-27T20:45:44Z
dc.date.available2025-01-27T20:45:44Z
dc.date.issued2017
dc.departmentÇanakkale Onsekiz Mart Üniversitesi
dc.description.abstractThe title dithiocarbamate compound was synthesized, and characterised by means of spectroscopic and single-crystal X-ray diffraction methods. Density functional theory method with the 6-311++G(d,p) basis set was employed to affirm the spectroscopic and structural properties and also to study the tautomerism in the compound. The obtained theoretical parameters clearly support the experimental findings. Among the six structural forms of the title compound, the syn-keto-amine-thione is found to be the most stable one, and the stability sequence is as the followings: syn-keto-amine-thione > anti-enolimine-thione > anti-keto-amine-thione > anti-keto-imine-thiol > syn-keto-imine-thiol > syn-enolimine-thione. The energy difference between the anti and syn forms changes from ca. 8-59 kJ morl(-1) with or without barriers. The energetic and thermodynamic findings of the syn-lceto-amine-thione reversible arrow syn-keto-irnine-thiol reaction display that the single proton exchange is unfavoured in both directions. Although the reverse barrier energy of the anti-enol-imine-thione reversible arrow anti-keto-imine-thiol tautomeric transformation is found to be small, neither the forward nor the reverse reaction appears to happen from the thermodynamic point of view. (C) 2017 Elsevier B.V. All rights reserved.
dc.description.sponsorshipGiresun University Scientific Research Foundation [FEN-BAP-A-200515-57]
dc.description.sponsorshipWe gratefully acknowledge the financial support of this work by the Giresun University Scientific Research Foundation (FEN-BAP-A-200515-57).
dc.identifier.doi10.1016/j.molstruc.2017.02.057
dc.identifier.endpage239
dc.identifier.issn0022-2860
dc.identifier.issn1872-8014
dc.identifier.scopus2-s2.0-85013040947
dc.identifier.scopusqualityQ1
dc.identifier.startpage233
dc.identifier.urihttps://doi.org/10.1016/j.molstruc.2017.02.057
dc.identifier.urihttps://hdl.handle.net/20.500.12428/24699
dc.identifier.volume1137
dc.identifier.wosWOS:000398870900025
dc.identifier.wosqualityQ3
dc.indekslendigikaynakWeb of Science
dc.indekslendigikaynakScopus
dc.language.isoen
dc.publisherElsevier Science Bv
dc.relation.ispartofJournal of Molecular Structure
dc.relation.publicationcategoryinfo:eu-repo/semantics/openAccess
dc.rightsinfo:eu-repo/semantics/closedAccess
dc.snmzKA_WoS_20250125
dc.subjectCrystal structure
dc.subjectSpectroscopy
dc.subjectDensity functional theory
dc.subjectRotamerism
dc.subjectTautomerism
dc.titleTautomerism in 4-chlorophenyl benzoylcarbamodithioate: Experimental and DFT study
dc.typeArticle

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