Synthesis, structural and spectroscopic studies of two new benzimidazole derivatives: A comparative study

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dc.contributor.authorSaral, Hasan
dc.contributor.authorOzdamar, Ozgur
dc.contributor.authorUcar, Ibrahim
dc.date.accessioned2025-03-23T19:39:37Z
dc.date.available2025-03-23T19:39:37Z
dc.date.issued2017
dc.departmentSinop Üniversitesi
dc.description.abstractIn the present work, structural and spectroscopic studies on 1-Methyl-2-(2'-hydroxy-4'-chlorophenyl) benzimidazole (1) and 1-Methyl-2-(2'-hydroxy-4'-methoxyphenyl)benzimidazole (2), have been carried out extensively by X-ray diffraction, HRMS, UV-Vis, FT-IR and H-1 and C-13 NMR spectroscopy. The crystal structure of both compounds is stabilized by O-H center dot center dot center dot N hydrogen bond and pi-pi interactions. Contrary to compound 1, the skeleton of compound 2 is considerably deviated from the planarity probably caused by intermolecular hydrogen bonding. The experimental results were compared to the theoretical ones, obtained at DFT level. Ground state geometry, electronic structure, vibrational and NMR spectra have been performed using the B3LYP functional with the 6-31 G(d,p) basis set. It was observed that the bond distances and angles in the both compounds were in good with those of the experiment. The energetic behaviors of the both compounds in methanol solvent were examined using by time-dependent DFT (TD-DFT) method by applying the polarizable continuum model (PCM). Isotropic chemical shifts (C-13 and H-1 NMR) were calculated using the gauge-invariant atomic orbital (GIAO) method. The HOMO and LUMO analyses were used to elucidate information regarding charge transfer within the molecule. (C) 2016 Elsevier B.V. All rights reserved.
dc.identifier.doi10.1016/j.molstruc.2016.10.013
dc.identifier.endpage54
dc.identifier.issn0022-2860
dc.identifier.issn1872-8014
dc.identifier.scopus2-s2.0-84989848475
dc.identifier.scopusqualityQ1
dc.identifier.startpage46
dc.identifier.urihttps://doi.org/10.1016/j.molstruc.2016.10.013
dc.identifier.urihttps://hdl.handle.net/11486/6402
dc.identifier.volume1130
dc.identifier.wosWOS:000390731800007
dc.identifier.wosqualityQ2
dc.indekslendigikaynakWeb of Science
dc.indekslendigikaynakScopus
dc.language.isoen
dc.publisherElsevier
dc.relation.ispartofJournal of Molecular Structure
dc.relation.publicationcategoryMakale - Uluslararası Hakemli Dergi - Kurum Öğretim Elemanı
dc.rightsinfo:eu-repo/semantics/closedAccess
dc.snmzKA_WOS_20250323
dc.subjectCharacterization
dc.subjectBenzimidazole
dc.subjectFT-IR
dc.subjectH-1 and C-13 NMR
dc.subjectDFT calculations
dc.titleSynthesis, structural and spectroscopic studies of two new benzimidazole derivatives: A comparative study
dc.typeArticle

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