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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.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 .
dc.identifier.otherPURE: 281846231
dc.identifier.otherPURE UUID: 1dba7628-ffc0-4c61-b197-ca965b3fcc19
dc.identifier.otherScopus: 85141889672
dc.identifier.otherWOS: 000886877800010
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.relation.ispartofActa Crystallographica Section C Structural Chemistryen
dc.rightsCopyright © The Author(s) 2022. This is an open-access article distributed under the terms of the Creative Commons Attribution (CC-BY) Licence, which permits unrestricted use, distribution, and reproduction in any medium, provided the original authors and source are cited.en
dc.subjectOxidative cyclocondensationen
dc.subjectMolecular hybridsen
dc.subjectMolecular structureen
dc.subjectMolecular conformationen
dc.subjectHydrogen bondingen
dc.subjectSupramolecular assemblyen
dc.subjectCrystal structureen
dc.subjectQD Chemistryen
dc.titleSynthesis, and spectroscopic and structural characterization of three new styrylquinoline–benzimidazole hybridsen
dc.typeJournal articleen
dc.description.versionPublisher PDFen
dc.contributor.institutionUniversity of St Andrews. School of Chemistryen
dc.description.statusPeer revieweden

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