Restricted rotation around the methylene bridge of 5-(2-p-(chlorophenyl)benzimidazole-1-yl)methyl-4-(o-substitutedphenyl)-2,4-dihydro-[1,2,4]-triazole-3-thiones as evidenced by NMR, X-RAY and DFT studies and the importance of low energy rotational conformers

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dc.authorscopusid15925274300
dc.authorscopusid7004145119
dc.authorscopusid6604012977
dc.authorscopusid6602166684
dc.contributor.authorKarayel, Arzu
dc.contributor.authorÖzbey, Süheyla
dc.contributor.authorKuş, Canan
dc.contributor.authorAyhan Kılcıgil, Gülgün
dc.date.accessioned2021-11-01T14:51:55Z
dc.date.available2021-11-01T14:51:55Z
dc.date.issued2019
dc.department[Belirlenecek]
dc.description.abstractThe aim of this study was to clarify the restricted rotation around the –CH2–N bond of the compounds, 5-(2-(p-chlorophenylbenzimidazol-1-yl-methyl)-4-(o-methylphenyl)-2,4-dihydro-[1,2,4]-triazole-3 thione [1], 4-(o-florophenyl)- [2], 4-(o-chlorophenyl)- [3] and 4-(o-bromophenyl)- [4], which are some benzimidazole derivatives showing antioxidant properties. In NMR spectra of relevant compounds, because of the hindered rotation around the methylene bridge, methylene protons appear as an AB quartet in DMSO?d6. The high temperature NMR spectra (296.1 K, 308.1 K, 323.1 K and 332.1 K) for the compound 1 show similar behavior in DMSO?d6. The NMR spectra in different solvents point out the same manner. The preventing of free rotation in the methylene bridge caused by the existence of substituents at the second position of the phenyl group connected to triazole ring was supported by both the experimental results (NMR and X-ray) and the theoretical results in the gas phase. The hindered rotation of compound 1 also investigated by applying the polarizable continuum model (PCM) for different solvents (DMSO?d6 and C6D6), as did in NMR. Additionally, potential energy surface (PES) scan revealed that each compound has two possible conformers. © 2018 Elsevier B.V.
dc.description.sponsorshipHacettepe Üniversitesi: 010T05604006en_US
dc.description.sponsorshipWe thank to the Unit of Scientific Research of Hacettepe University with the number of 010T05604006 Project as a part of the Ph.D Thesis.en_US
dc.identifier.doi10.1016/j.molstruc.2018.09.083
dc.identifier.endpage484en_US
dc.identifier.issn0022-2860
dc.identifier.scopus2-s2.0-85056185630
dc.identifier.scopusqualityQ1
dc.identifier.startpage476en_US
dc.identifier.urihttps://doi.org/10.1016/j.molstruc.2018.09.083
dc.identifier.urihttps://hdl.handle.net/11491/6381
dc.identifier.volume1177en_US
dc.indekslendigikaynakScopus
dc.institutionauthorKarayel, Arzu
dc.language.isoen
dc.publisherElsevier B.V.
dc.relation.ispartofJournal of Molecular Structure
dc.relation.publicationcategoryMakale - Uluslararası Hakemli Dergi - Kurum Öğretim Elemanı
dc.rightsinfo:eu-repo/semantics/closedAccess
dc.subject1,2,4-Triazoleen_US
dc.subjectAntioxidanten_US
dc.subjectBenzimidazoleen_US
dc.subjectConformeren_US
dc.subjectDFTen_US
dc.subjectX-ray diffractionen_US
dc.titleRestricted rotation around the methylene bridge of 5-(2-p-(chlorophenyl)benzimidazole-1-yl)methyl-4-(o-substitutedphenyl)-2,4-dihydro-[1,2,4]-triazole-3-thiones as evidenced by NMR, X-RAY and DFT studies and the importance of low energy rotational conformers
dc.typeArticle

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