Synthesis, crystal structures, spectral investigations, conformational analysis and DFT studies of N- heterocyclic carbene precursors

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dc.authoridAktaş, Aydın/0000-0001-8496-6782;
dc.authorwosidBarut Celepci, Duygu/M-6189-2017
dc.authorwosidAktaş, Aydın/J-6194-2019
dc.authorwosidGök, Yetkin/AAA-5669-2021
dc.contributor.authorErdemir, Fatos
dc.contributor.authorCelepci, Duygu Barut
dc.contributor.authorAktas, Aydin
dc.contributor.authorGok, Yetkin
dc.date.accessioned2024-08-04T20:47:02Z
dc.date.available2024-08-04T20:47:02Z
dc.date.issued2020
dc.departmentİnönü Üniversitesien_US
dc.description.abstractThree new 2-hydroxyethyl substituted N-heterocyclic carbene (NHC) precursors were synthesized in this study. These NHC precursors were prepared from 1-(alkyl/aryl)benzimidazole and alkyl halides. Their structural characterizations were performed by elemental analysis, H-1 NMR, C-13 NMR, FT-IR and UV-Vis spectroscopy and single-crystal X-ray diffraction. The spectral features were also characterized by Density Functional Theory (DFT) at B3LYP/Lanl2dz//6-31G++(d,p) basis set. Two most stable conformers belonging to the compounds were found by potential energy surface (PES) scan, and the theoretical ground-state geometries were investigated. Among these conformers, the geometry of the conformer-I for all compounds matches almost well with the experimental results. H-1 and C-13 NMR chemical shifts were calculated with GLAD approach and compared to the observed ones. Detailed vibrational assignments of the wavenumbers of the conformers were carried out based on the potential energy distribution (PED). Natural bond orbital (NBO) analysis was used to analyze the stability of the molecules arising from hyperconjugative interactions and charge delocalization. The HOMO-LUMO energy gap of the stable conformers was calculated for comparing their chemical reactivity behavior. Molecular electrostatic potential (MEP) diagrams were used to get information about ?the size, shape, charge density distribution and site of chemical reactivity of each stable conformer. The 3D Hirshfeld surfaces and the associated 2D fingerprint plots were also carried out to obtain an insight into the behavior of the interactions in the compounds. (C) 2019 Elsevier B.V. All rights reserved.en_US
dc.description.sponsorshipDokuz Eylul University [2010 KB.FEN.13]en_US
dc.description.sponsorshipThe authors acknowledge Inonu University Scientific and Technology Center for the elemental analyses of the compounds and Dokuz Eylul University for the use of the Rigaku Oxford Xca-libur Eos Diffractometer (purchased under University Research Grant No: 2010 KB.FEN.13). The authors also thank to Muhittin Aygun for the use of Gaussian 09W/Gauss View package programs.en_US
dc.identifier.doi10.1016/j.molstruc.2019.127519
dc.identifier.issn0022-2860
dc.identifier.issn1872-8014
dc.identifier.scopus2-s2.0-85076405421en_US
dc.identifier.scopusqualityQ2en_US
dc.identifier.urihttps://doi.org/10.1016/j.molstruc.2019.127519
dc.identifier.urihttps://hdl.handle.net/11616/99099
dc.identifier.volume1204en_US
dc.identifier.wosWOS:000508216300068en_US
dc.identifier.wosqualityQ3en_US
dc.indekslendigikaynakWeb of Scienceen_US
dc.indekslendigikaynakScopusen_US
dc.language.isoenen_US
dc.publisherElsevieren_US
dc.relation.ispartofJournal of Molecular Structureen_US
dc.relation.publicationcategoryMakale - Uluslararası Hakemli Dergi - Kurum Öğretim Elemanıen_US
dc.rightsinfo:eu-repo/semantics/closedAccessen_US
dc.subjectN-heterocyclic carbeneen_US
dc.subjectCrystal structureen_US
dc.subjectSpectral investigationsen_US
dc.subjectConformational analysisen_US
dc.subjectDFTen_US
dc.titleSynthesis, crystal structures, spectral investigations, conformational analysis and DFT studies of N- heterocyclic carbene precursorsen_US
dc.typeArticleen_US

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