A comparative study of X-ray structural analysis, supramolecular investigation by Hirshfeld surface analysis and DFT computations for tricyclic 1,4-benzodiazepines

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dc.authoridAshfaq, Muhammad/0000-0001-6663-8777
dc.authoridSahin, Onur/0000-0003-3765-3235
dc.authoridAl-Salahi, Rashad/0000-0003-1747-2736
dc.authoridKurbanova, Malahat/0000-0001-9857-9505
dc.authoridEl Bakri, Youness/0000-0002-5759-6568
dc.contributor.authorKurbanova, Malahat
dc.contributor.authorAhsin, Atazaz
dc.contributor.authorAliyev, Gaya
dc.contributor.authorAshfaq, Muhammad
dc.contributor.authorSahin, Onur
dc.contributor.authorTahir, Muhammad Nawaz
dc.contributor.authorAbuelizz, Hatem A.
dc.date.accessioned2025-03-23T19:39:17Z
dc.date.available2025-03-23T19:39:17Z
dc.date.issued2025
dc.departmentSinop Üniversitesi
dc.description.abstractThe tricyclic 1,4-benzodiazepines - seven-membered heterocyclic compounds were synthesized derived from the three-component reaction involving o-phenylenediamine, 5,5-dimethyl-1,3-cyclohexanedione and various aromatic aldehydes under the influence of HCl. The crystal structure of 11-(3-nitrophenyl)-3,3-dimethyl2,3,4,5,10,11-hexahydro-1H-dibenzo[b,e][1,4]diazepin-1-one (NDDD) and 11-(2-chlorophenyl)-3,3-dimethyl2,3,4,5,10,11-hexahydro-1H-dibenzo[b,e][1,4]diazepin-1-one (CDDD) corroborated through single crystal X-ray diffraction method. The Hirshfeld surface analysis indicates crystal packing along with role of intermolecular forces in stabilizing supramolecular assembly of NDDD and CDDD. 2D fingerprint analysis is carried out to envisage to the elemental interactions in the assumption of a single crystal containing molecular fragments. DFT investigations have been carried out to understand the reactivity of NDDD and CDDD at the m062x/def2tzvp method. The obtained geometric parameters from theoretical study are well consistent with experimentally reported XRD analysis. Bonding analysis and charge transfer were examined by performing quantum theory of atoms in molecules (QTAIM) and natural bonding orbital (NBO) analysis. The synthesized NDDD and CDDD exhibit excellent electronic and nonlinear optical properties. The NLO response is justified through computed hyperpolarizability values.
dc.description.sponsorshipKing Saud University, Riyadh, Saudi Arabia [RSPD2024R566]
dc.description.sponsorshipThis research was funded by Researchers Supporting Project No RSPD2024R566, King Saud University, Riyadh, Saudi Arabia.
dc.identifier.doi10.1016/j.molstruc.2024.140531
dc.identifier.issn0022-2860
dc.identifier.issn1872-8014
dc.identifier.scopus2-s2.0-85208380764
dc.identifier.scopusqualityQ1
dc.identifier.urihttps://doi.org/10.1016/j.molstruc.2024.140531
dc.identifier.urihttps://hdl.handle.net/11486/6309
dc.identifier.volume1322
dc.identifier.wosWOS:001355468700001
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.subjectTricyclic 1
dc.subject4-benzodiazepines
dc.subjectCrystal structure
dc.subjectHirshfeld surface analysis
dc.subjectNBO-NLO analysis
dc.subjectQTAIM
dc.titleA comparative study of X-ray structural analysis, supramolecular investigation by Hirshfeld surface analysis and DFT computations for tricyclic 1,4-benzodiazepines
dc.typeArticle

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