Synthesis, spectroscopic characterization and DFT calculations of N-Methyl-2-(2′-hydroxyphenyl)benzimidazole derivatives

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dc.authoridAygun, Muhittin/0000-0001-9670-9062
dc.authoridBekdemir, Yunus/0009-0004-8521-395X
dc.contributor.authorSaral, Hasan
dc.contributor.authorOzdamar, Ozgur
dc.contributor.authorUcar, Ibrahim
dc.contributor.authorBekdemir, Yunus
dc.contributor.authorAygun, Muhittin
dc.date.accessioned2025-03-23T19:40:47Z
dc.date.available2025-03-23T19:40:47Z
dc.date.issued2016
dc.departmentSinop Üniversitesi
dc.description.abstract1-Methy1-2-(2'-hydroxyphenyl)benzimidazole (1) and 1-Methy1-2-(2'-hydroxy-4'-methylphenyl)benzimidazole (2) compounds have been synthesized and characterized by XRD, IE-MS, FT-IR, UV Vis and H-1, C-13 NMR techniques. The crystal structure of both compounds is stabilized with very strong O-H center dot center dot center dot N hydrogen-bond and pi-pi interactions. In the compound 1, an infinite chain structure with a trans-zigzag type was formed along the crystallographic 11011 direction. Quantum mechanical calculations of energies, geometries, vibrational wavenumbers, NMR and electronic transitions were carried out by DFT using B3LYP functional combined with 6.31G(d,p) basis set. Calculated bond lengths, bond angles and dihedral angles were only slightly different from the experimental ones. The vibrational study was interpreted by means of potential energy distribution (PED). The electronic absorption spectra of the both compounds were predicted by using the time-dependent DFT methods and good agreement was found between the computational and the experimental values. The chemical shifts (H-1 and (1)3C NMR) and isotropic shielding values were calculated by using the gauge-invariant atomic orbital (GIAO) method. The analyses of HOMO and LUMO have been used to explain the charge transfer within the molecule. (C) 2015 Elsevier B.V. All rights reserved.
dc.identifier.doi10.1016/j.molstruc.2015.09.010
dc.identifier.endpage19
dc.identifier.issn0022-2860
dc.identifier.issn1872-8014
dc.identifier.scopus2-s2.0-84941662224
dc.identifier.scopusqualityQ1
dc.identifier.startpage9
dc.identifier.urihttps://doi.org/10.1016/j.molstruc.2015.09.010
dc.identifier.urihttps://hdl.handle.net/11486/6411
dc.identifier.volume1103
dc.identifier.wosWOS:000364726700002
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.subjectBenzimidazole derivatives
dc.subjectX-ray diffraction
dc.subjectFT-IR
dc.subjectH-1 and C-13 NMR
dc.subjectUV-Vis
dc.subjectDFT
dc.titleSynthesis, spectroscopic characterization and DFT calculations of N-Methyl-2-(2′-hydroxyphenyl)benzimidazole derivatives
dc.typeArticle

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