Regioselectivity in the nitration of eugenol is independent of inorganic reagents : an experimental and theoretical investigation with synthetic and mechanistic implications

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MetadadosDescriçãoIdioma
Autor(es): dc.contributorUniversidade Federal da Bahia, Instituto de Química-
Autor(es): dc.contributorUniversidade Federal da Bahia, Instituto de Química-
Autor(es): dc.contributorUniversidade Federal da Bahia, Instituto de Química-
Autor(es): dc.contributorUniversidade de Brasília, Faculdade de Ciências da Saúde, Departamento de Farmácia-
Autor(es): dc.contributorUniversidade Federal de Goiás, Instituto de Química, Laboratório de RMN-
Autor(es): dc.contributorUniversidade Federal da Bahia, Instituto de Química-
Autor(es): dc.contributorInstituto Nacional de Ciência e Tecnologia – INCT em Energia e Ambiente, Campus Ondina, Salvador-
Autor(es): dc.creatorBarbosa, Jaqueline Rosa Cardoso-
Autor(es): dc.creatorQueiroz, Murillo Halo-
Autor(es): dc.creatorRivelino, Roberto-
Autor(es): dc.creatorOliveira, Gerlon de Almeida Ribeiro-
Autor(es): dc.creatorLião, Luciano Morais-
Autor(es): dc.creatorCunha, Silvio-
Data de aceite: dc.date.accessioned2024-10-23T15:06:27Z-
Data de disponibilização: dc.date.available2024-10-23T15:06:27Z-
Data de envio: dc.date.issued2024-07-03-
Data de envio: dc.date.issued2024-07-03-
Data de envio: dc.date.issued2023-12-27-
Fonte completa do material: dc.identifierhttp://repositorio2.unb.br/jspui/handle/10482/48509-
Fonte completa do material: dc.identifierhttps://doi.org/10.1021/acs.joc.3c02298-
Fonte completa do material: dc.identifierhttps://orcid.org/0000-0003-0956-7903-
Fonte completa do material: dc.identifierhttps://orcid.org/0000-0003-2679-1640-
Fonte completa do material: dc.identifierhttps://orcid.org/0000-0001-9985-2980-
Fonte completa do material: dc.identifierhttps://orcid.org/0000-0002-8822-517X-
Fonte: dc.identifier.urihttp://educapes.capes.gov.br/handle/capes/874474-
Descrição: dc.descriptionIn 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.-
Descrição: dc.descriptionFaculdade de Ciências da Saúde (FS)-
Descrição: dc.descriptionDepartamento de Farmácia (FS FAR)-
Idioma: dc.languageen-
Publicador: dc.publisherAmerican Chemical Society-
Relação: dc.relationhttps://pubs.acs.org/doi/10.1021/acs.joc.3c02298?ref=PDF#-
Direitos: dc.rightsAcesso Restrito-
Palavras-chave: dc.subjectEnergia-
Palavras-chave: dc.subjectHidratação-
Palavras-chave: dc.subjectEstrutura molecular-
Palavras-chave: dc.subjectMoléculas-
Palavras-chave: dc.subjectReações orgânicas-
Título: dc.titleRegioselectivity in the nitration of eugenol is independent of inorganic reagents : an experimental and theoretical investigation with synthetic and mechanistic implications-
Tipo de arquivo: dc.typelivro digital-
Aparece nas coleções:Repositório Institucional – UNB

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