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dc.contributor.authorCobo, Justospa
dc.contributor.authorVicentes, Daniel E.spa
dc.contributor.authorRodríguez, Ricaurtespa
dc.contributor.authorMarchal, Antoniospa
dc.contributor.authorGlidewell, Christopherspa
dc.date.accessioned2019-10-10T20:58:50Zspa
dc.date.available2019-10-10T20:58:50Zspa
dc.date.issued2018spa
dc.identifier.citationCobo, J., Vicentes, D. E., Rodríguez, R., Marchal, A., & Glidewell, C. (2018). A concise synthesis of a highly substituted 6-(1H-benzimidazol-1-yl)-5-nitrosopyrimidin-2- amine: Synthetic sequence and the molecular and supramolecular structures of one product and two intermediates. Acta Crystallographica Section C: Structural Chemistry, 74, 696-702. doi:10.1107/S2053229618007015spa
dc.identifier.urihttps://www.scopus.com/search/form.uri?display=basicspa
dc.description.abstractA concise and efficient synthesis of 6-benzimidazolyl-5-nitrosopyrimidines has been developed using Schiff base-type intermediates derived from N4-(2-aminophenyl)-6-methoxy-5-nitrosopyrimidine-2,4-diamine. 6-Methoxy-N4-{2-[(4-methylbenzylidene)amino]phenyl}-5-nitrosopyrimidine-2,4-diamine, (I), and N4-{2-[(ethoxymethylidene)amino]phenyl}-6-methoxy-5-nitrosopyrimidine-2,4-diamine, (III), both crystallize from dimethyl sulfoxide solution as the 1:1 solvates C19H18N6O2·C2H6OS, (Ia), and C14H16N6O3·C2H6OS, (IIIa), respectively. The interatomic distances in these intermediates indicate significant electronic polarization within the substituted pyrimidine system. In each of (Ia) and (IIIa), intermolecular N-H…O hydrogen bonds generate centrosymmetric four-molecule aggregates. Oxidative ring closure of intermediate (I), effected using ammonium hexanitratocerate(IV), produced 4-methoxy-6-[2-(4-methylphenyl-1H-benzimidazol-1-yl]-5-nitrosopyrimidin-2-amine, C19H16N6O2, (II) [Cobo et al. (2018). Private communication (CCDC 1830889). CCDC, Cambridge, England], where the extent of electronic polarization is much less than in (Ia) and (IIIa). A combination of N–H…N and C–H…O hydrogen bonds links the molecules of (II) into complex sheets.eng
dc.format.mimetypeapplication/pdfspa
dc.language.isoengspa
dc.relation.ispartofseriesActa Crystallographica Section C: Structural Chemistry;Vol.74, 2018 páginas 696-702spa
dc.rightsDerechos Reservados - Universidad de Ciencias Aplicadas y Ambientalesspa
dc.rights.urihttps://creativecommons.org/licenses/by-sa/4.0/spa
dc.sourcehttps://www.scopus.com/search/form.uri?display=basicspa
dc.sourcehttps://www.scopus.com/search/form.uri?display=basicspa
dc.subject.meshBisbenzimidazolspa
dc.subject.meshSíntesis químicaspa
dc.subject.meshEnlaces de Hidrógenospa
dc.subject.meshEstructura Molecularspa
dc.titleA concise synthesis of a highly substituted 6-(1H-benzimidazol-1-yl)-5-nitrosopyrimidin-2- amine: Synthetic sequence and the molecular and supramolecular structures of one product and two intermediatesspa
dc.typeArtículo de revistaspa
dc.rights.accessrightsinfo:eu-repo/semantics/openAccessspa
dc.identifier.doi10.1107/S2053229618007015spa
dc.rights.creativecommonsAtribución-CompartirIgual 4.0 Internacional (CC BY-SA 4.0)spa
dc.subject.proposalBenzimidazolespa
dc.subject.proposalCrystal structurespa
dc.subject.proposalElectronic polarizationspa
dc.subject.proposalHeterocyclic compoundspa
dc.subject.proposalHydrogen bondingspa
dc.subject.proposalMolecular structurespa
dc.subject.proposalNitrosopyrimidinespa
dc.subject.proposalSupramolecular aggregationspa
dc.subject.proposalSynthesisspa
dc.type.coarhttp://purl.org/coar/resource_type/c_6501spa
dc.type.driverinfo:eu-repo/semantics/articlespa
dc.type.versioninfo:eu-repo/semantics/publishedVersionspa
dc.type.contentTextspa
dc.type.redcolhttp://purl.org/redcol/resource_type/ARTspa
oaire.accessrightshttp://purl.org/coar/access_right/c_abf2spa
oaire.versionhttp://purl.org/coar/version/c_970fb48d4fbd8a85spa


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Derechos Reservados - Universidad de Ciencias Aplicadas y Ambientales
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