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Determination of the tautomerism of albendazole desmotropes using solution and solid state NMR together with DFT theoretical calculations, both energies and chemical shifts

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dc.contributor.authorClaramunt Vallespí, Rosa María
dc.contributor.authorLópez García, Concepción
dc.contributor.authorSanz del Castillo, Dionisia
dc.contributor.authorElguero, José
dc.contributor.authorAlkorta, Ibon
dc.date.accessioned2024-09-27T08:29:55Z
dc.date.available2024-09-27T08:29:55Z
dc.date.issued2022-08-05
dc.description.abstractThis paper reports a structural study of albendazole concerning the desmotropy of its amino and imino tautomers, ABZ-I and ABZ-II, mistakenly called polymorphs. Experimental NMR determination in solution, DMSO-d6, HMPA-d18 and CF3 CO2 H, and in the solid state, CPMAS, together with DFT calculations, energies and NMR chemical shifts, has allowed to understand the complex problem of prototropy combined with rotation about the benzimidazole C2-N exocyclic group that explain the disorder problem of the S-propyl group. The structure of protonated albendazole, ABZH +, has also been studied. The role of the hybrid HF/DFT B3LYP computational method at the B3LYP/6-311++G(d,p) level has been determinant to solve the problems related to the structure of albendazole in the solid state and in solution and the barrier in solution of a phenomenon resulting either from annular tautomerism or from the rotation about the exocyclic C-N bond.en
dc.description.versionversión final
dc.identifier.citationRosa M. Claramunt, Concepción López, Dionisia Sanz, José Elguero, Ibon Alkorta, Determination of the tautomerism of albendazole desmotropes using solution and solid state NMR together with DFT theoretical calculations, both energies and chemical shifts, Journal of Molecular Structure, Volume 1261, 2022, 132883, ISSN 0022-2860, https://doi.org/10.1016/j.molstruc.2022.132883
dc.identifier.doihttps://doi.org/10.1016/j.molstruc.2022.132883
dc.identifier.issn0022-2860
dc.identifier.urihttps://hdl.handle.net/20.500.14468/23837
dc.journal.titleJournal of Molecular Structure
dc.journal.volume1261
dc.language.isoen
dc.publisherElsevier
dc.relation.centerFacultades y escuelas::Facultad de Ciencias
dc.relation.departmentQuímica Orgánica y Bio-Orgánica
dc.rightsinfo:eu-repo/semantics/openAccess
dc.rights.licenseAtribución-NoComercial-SinDerivadas 4.0 Internacional
dc.rights.urihttps://creativecommons.org/licenses/by-nc-nd/4.0/deed.es
dc.subject23 Química
dc.subject.keywordsAlbendazoleen
dc.subject.keywordsPolymorphsen
dc.subject.keywordsDesmotropesen
dc.subject.keywordsNMR crystallographyen
dc.subject.keywordsDFTen
dc.subject.keywordsGIAOen
dc.titleDetermination of the tautomerism of albendazole desmotropes using solution and solid state NMR together with DFT theoretical calculations, both energies and chemical shiftsen
dc.typeartículoes
dc.typejournal articleen
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relation.isAuthorOfPublication2545e8b7-8504-4d33-8f3f-f0c11afcc748
relation.isAuthorOfPublicationc4e6468b-75c5-452b-bf12-9637dd3519f3
relation.isAuthorOfPublication.latestForDiscoveryc4e6468b-75c5-452b-bf12-9637dd3519f3
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