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dc.contributor.authorArdila, Diana M.
dc.contributor.authorRodriguez, Diego F.
dc.contributor.authorPalma, Alirio
dc.contributor.authorDiaz, Ivan
dc.contributor.authorCobo, Justo
dc.contributor.authorGlidewell, Christopher
dc.date.accessioned2022-10-26T06:30:15Z
dc.date.available2022-10-26T06:30:15Z
dc.date.issued2022-11-01
dc.identifier281846231
dc.identifier1dba7628-ffc0-4c61-b197-ca965b3fcc19
dc.identifier85141889672
dc.identifier000886877800010
dc.identifier.citationArdila , D M , Rodriguez , D F , Palma , A , Diaz , I , Cobo , J & Glidewell , C 2022 , ' Synthesis, and spectroscopic and structural characterization of three new styrylquinoline–benzimidazole hybrids ' , Acta Crystallographica Section C Structural Chemistry , vol. 78 , no. 11 , pp. 671-680 . https://doi.org/10.1107/S2053229622010063en
dc.identifier.issn2053-2296
dc.identifier.urihttps://hdl.handle.net/10023/26246
dc.descriptionFunding for this research was provided by: Vicerrectoría de Investigación y Extensión of the Industrial University of Santander (grant No. 2680)en
dc.description.abstractThree new 4-styryl­quinoline–benzimidazole hybrids have been synthesized using a reaction sequence in which 2-methyl­quinoline precursors first undergo selective oxidation by selenium dioxide to form the corresponding 2-formyl­quinoline inter­mediates, followed by oxidative cyclo­condensation reactions with benzene-1,2-diamine to yield the hybrid products. The formyl inter­mediates and the hybrid products have all been fully characterized using a combination of IR, 1H and 13C NMR spectroscopy, and high-resolution mass spectrometry, and the structures of the three hybrid products have been determined using single-crystal X-ray diffraction. Ethyl (E)-2-(1H-benzo[d]imidazol-2-yl)-4-(4-chloro­styr­yl)quinoline-3-carboxyl­ate, C27H20ClN3O2, (IIIa), and ethyl (E)-2-(1H-ben­zo[d]imidazol-2-yl)-4-(2-meth­oxy­styr­yl)quinoline-3-carboxyl­ate, C28H23N3O3, (IIIb), both crystallize in the solvent-free form with Z′ = 1, but ethyl (E)-2-(1H-benzo[d]imidazol-2-yl)-4-(4-methyl­styr­yl)quinoline-3-carboxyl­ate, C28H23N3O2, (IIIc), crystallizes as a partial hexane solvate with Z′ = 3, and the ester group in one of the independent mol­ecules is disordered over two sets of atomic sites having occupancies of 0.765 (7) and 0.235 (7). The mol­ecules of (IIIc) enclose continuous channels which are occupied by disordered solvent mol­ecules having partial occupancy. In all of the mol­ecules of (IIIa)–(IIIc), the styryl­quinoline fragment is markedly nonplanar. Different combinations of N—H⋯O and C—H⋯π hydrogen bonds generate supra­molecular assemblies which are two-dimensional in (IIIb) and (IIIc), but three-dimensional in (IIIa). Comparisons are made with the structures of some related com­pounds.
dc.format.extent10
dc.format.extent1662699
dc.language.isoeng
dc.relation.ispartofActa Crystallographica Section C Structural Chemistryen
dc.subjectSynthesisen
dc.subjectOxidative cyclocondensationen
dc.subjectStyrylquinolineen
dc.subjectBenzimidazoleen
dc.subjectMolecular hybridsen
dc.subjectMolecular structureen
dc.subjectMolecular conformationen
dc.subjectHydrogen bondingen
dc.subjectSupramolecular assemblyen
dc.subjectCrystal structureen
dc.subjectQD Chemistryen
dc.subjectDASen
dc.subjectNISen
dc.subjectMCCen
dc.subject.lccQDen
dc.titleSynthesis, and spectroscopic and structural characterization of three new styrylquinoline–benzimidazole hybridsen
dc.typeJournal articleen
dc.contributor.institutionUniversity of St Andrews. School of Chemistryen
dc.identifier.doi10.1107/S2053229622010063
dc.description.statusPeer revieweden


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