Influence of the haloaryl moiety over the molecular packing in N-phenacylbenzimidazoles crystallizing in the same space group

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dc.contributor.authorVargas Oviedo, Diana
dc.contributor.authorPortilla, Jaime
dc.contributor.authorMacías, Mario A.
dc.date.accessioned2021-03-08T16:05:37Z
dc.date.available2021-03-08T16:05:37Z
dc.date.issued2021
dc.description.abstractenglishIn this study, a family of N -phenacylbenzimidazoles 1–3 synthesized in high yields (90–93%) by the N - phenacylation reaction of NH -benzimidazole ( 4 ) under ultrasonic conditions was recrystallized from the mixture EtOH:AcOEt (1:1 V/V). These compounds crystallize in the same Monoclinic P 2 1 / c space group, though the molecular packing is affected by the haloaryl group varying the final crystal structure. The para substitution of the halogen atom in the aryl ring influences a more pronounced electronic defi- ciency over the methylene bridge allowing the formation of intermolecular C–H ···O hydrogen bonds in compounds 1 and 3 . Additionally, in compound 2 , the ortho substitution of an F atom, not only affects the electron density but also blocks this CH 2 group with an intramolecular C–H ···O hydrogen bond. Re- markably after the crystallization process, compound 3 crystallizes as a cocrystal with a 4-fluorobenzoic acid molecule obtained by hydrolysis of 3 . This co-crystallization affects dramatically the total packing energies from values of -138.7/-135.2 kJ/mol for 1 and 2 , respectively, to -229.7 kJ/mol for compound 3 .eng
dc.format.mimetypeapplication/pdf
dc.identifier.doihttps://doi.org/10.1016/j.molstruc.2020.129869
dc.identifier.instnameinstname:Universidad El Bosquespa
dc.identifier.issn1872-8014
dc.identifier.reponamereponame:Repositorio Institucional Universidad El Bosquespa
dc.identifier.repourlrepourl:https://repositorio.unbosque.edu.co
dc.identifier.urihttps://hdl.handle.net/20.500.12495/5566
dc.language.isoeng
dc.publisherElsevier B.V.spa
dc.publisher.journalJournal of Molecular Structurespa
dc.relation.ispartofseriesJournal of Molecular Structure, 1872-8014, Vol. 1230, 2021, p.129869spa
dc.relation.urihttps://www.sciencedirect.com/science/article/abs/pii/S0022286020321827?via%3Dihub
dc.rights.accessrightshttps://purl.org/coar/access_right/c_abf2
dc.rights.accessrightsinfo:eu-repo/semantics/openAccess
dc.rights.accessrightsAcceso abierto
dc.rights.creativecommons2021
dc.rights.localAcceso abiertospa
dc.subject.keywordsBenzimidazolespa
dc.subject.keywordsCocrystalspa
dc.subject.keywordsHirshfeld surface mapsspa
dc.subject.keywordsMolecular packingspa
dc.subject.keywordsN -Phenacylbenzimidazolesspa
dc.titleInfluence of the haloaryl moiety over the molecular packing in N-phenacylbenzimidazoles crystallizing in the same space groupspa
dc.title.translatedInfluence of the haloaryl moiety over the molecular packing in N-phenacylbenzimidazoles crystallizing in the same space groupspa
dc.type.coarhttps://purl.org/coar/resource_type/c_6501
dc.type.driverinfo:eu-repo/semantics/article
dc.type.hasversioninfo:eu-repo/semantics/publishedVersion
dc.type.localArtículo de revista

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