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dc.contributor.authorBarbosa, Jaqueline Rosa Cardoso-
dc.contributor.authorQueiroz, Murillo Halo-
dc.contributor.authorRivelino, Roberto-
dc.contributor.authorOliveira, Gerlon de Almeida Ribeiro-
dc.contributor.authorLião, Luciano Morais-
dc.contributor.authorCunha, Silvio-
dc.date.accessioned2024-07-03T12:52:40Z-
dc.date.available2024-07-03T12:52:40Z-
dc.date.issued2023-12-28-
dc.identifier.citationBARBOSA, Jaqueline Rosa Cardoso et al. Regioselectivity in the nitration of eugenol is independent of inorganic reagents: an experimental and theoretical investigation with synthetic and mechanistic implications. The Journal of Organic Chemistry, [S. l.], v. 89, n. 2, p. 1120–1126, 2024. DOI: https://doi.org/10.1021/acs.joc.3c02298.pt_BR
dc.identifier.urihttp://repositorio2.unb.br/jspui/handle/10482/48509-
dc.language.isoengpt_BR
dc.publisherAmerican Chemical Societypt_BR
dc.rightsAcesso Restritopt_BR
dc.titleRegioselectivity in the nitration of eugenol is independent of inorganic reagents : an experimental and theoretical investigation with synthetic and mechanistic implicationspt_BR
dc.typeArtigopt_BR
dc.subject.keywordEnergiapt_BR
dc.subject.keywordHidrataçãopt_BR
dc.subject.keywordEstrutura molecularpt_BR
dc.subject.keywordMoléculaspt_BR
dc.subject.keywordReações orgânicaspt_BR
dc.identifier.doihttps://doi.org/10.1021/acs.joc.3c02298pt_BR
dc.relation.publisherversionhttps://pubs.acs.org/doi/10.1021/acs.joc.3c02298?ref=PDF#pt_BR
dc.description.abstract1In this study, we reinvestigated the straightforward nitration of eugenol using traditional reagents and bismuth nitrate. NMR analysis of the obtained products revealed that the regioselectivity of eugenol nitration was independent of the inorganic nitrating reagent used, consistently resulting in the formation of 6-nitroeugenol. This contradicts previous literature reports because the elusive synthesis of 5-nitroeugenol using Bi(NO3)3·5H2O was not achievable through straightforward methods; instead, this isomer could only be prepared via the well-established three-step synthesis. Theoretical investigations using DFT calculations, considering both the dielectric constant of the medium and explicit water molecules, substantiated this regioselectivity. It was found that hydration water played a critical role in the formation of a Zundel cation, shifting the thermodynamic equilibrium toward the exclusive production of 6-nitroeugenol. These results imply that all biological studies involving eugenol derivatives synthesized via direct nitration with Bi(NO3)3·5H2O should be reviewed, as they dealt with 6-substituted eugenol derivatives rather than the previously assumed 5-substituted eugenol.pt_BR
dc.identifier.orcidhttps://orcid.org/0000-0003-0956-7903pt_BR
dc.identifier.orcidhttps://orcid.org/0000-0003-2679-1640pt_BR
dc.identifier.orcidhttps://orcid.org/0000-0001-9985-2980pt_BR
dc.identifier.orcidhttps://orcid.org/0000-0002-8822-517Xpt_BR
dc.contributor.affiliationUniversidade Federal da Bahia, Instituto de Químicapt_BR
dc.contributor.affiliationUniversidade Federal da Bahia, Instituto de Químicapt_BR
dc.contributor.affiliationUniversidade Federal da Bahia, Instituto de Químicapt_BR
dc.contributor.affiliationUniversidade de Brasília, Faculdade de Ciências da Saúde, Departamento de Farmáciapt_BR
dc.contributor.affiliationUniversidade Federal de Goiás, Instituto de Química, Laboratório de RMNpt_BR
dc.contributor.affiliationUniversidade Federal da Bahia, Instituto de Químicapt_BR
dc.contributor.affiliationInstituto Nacional de Ciência e Tecnologia – INCT em Energia e Ambiente, Campus Ondina, Salvadorpt_BR
dc.description.unidadeFaculdade de Ciências da Saúde (FS)pt_BR
dc.description.unidadeDepartamento de Farmácia (FS FAR)pt_BR
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