Theoretical and X-Ray evidence of electrostatic phosphonium anti and gauche effects

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MetadadosDescriçãoIdioma
Autor(es): dc.creatorMartins, Francisco A.-
Autor(es): dc.creatorChagas, Poliane-
Autor(es): dc.creatorThomasi, Sérgio S.-
Autor(es): dc.creatorOliveira, Luiz C. A.-
Autor(es): dc.creatorDiniz, Renata-
Autor(es): dc.creatorFreitas, Matheus P.-
Data de aceite: dc.date.accessioned2026-02-09T12:09:02Z-
Data de disponibilização: dc.date.available2026-02-09T12:09:02Z-
Data de envio: dc.date.issued2022-09-06-
Data de envio: dc.date.issued2022-09-06-
Data de envio: dc.date.issued2021-12-
Fonte completa do material: dc.identifierhttps://repositorio.ufla.br/handle/1/54489-
Fonte completa do material: dc.identifierhttps://doi.org/10.1002/cphc.202100856-
Fonte: dc.identifier.urihttp://educapes.capes.gov.br/handle/capes/1155408-
Descrição: dc.descriptionSulphur, not phosphorus, is the only known third-row element capable of experiencing an electrostatic gauche effect with fluorine. Some six-membered rings containing an endocyclic phosphorus atom and a β-fluorine substituent that can interconvert to axial (gauche relative to phosphorus) and equatorial positions were then analysed. While phosphines do not establish an electrostatic attraction between fluorine and phosphorus, some oxidised forms exhibit surprising stability for the sterically disfavoured axial orientation. Because the nature of this behaviour was not obvious, since an intramolecular hydrogen bond can appear, a phosphonium derivative was further studied and its axial conformation was found to be highly stable. A preference for the gauche arrangement appears even for the acyclic and sterically hindered (2-fluoroethyl)triphenylphosphonium cation. On the other hand, (ethane-1,2-diyl)bis(phosphonium) cations are exclusively in anti conformation due to an (+/+)-electrostatic repulsion between the positively charged phosphonium groups.-
Idioma: dc.languageen-
Publicador: dc.publisherJohn Wiley & Sons, Inc. / Chemistry Europe-
Direitos: dc.rightsrestrictAccess-
???dc.source???: dc.sourceChemPhysChem-
Palavras-chave: dc.subjectConformational analysis-
Palavras-chave: dc.subjectGauche effect-
Palavras-chave: dc.subjectAnti effect-
Palavras-chave: dc.subjectOrganophosphorus compounds-
Palavras-chave: dc.subjectElectrostatic interactions-
Palavras-chave: dc.subjectAnálise Conformacional-
Palavras-chave: dc.subjectEfeito gauche-
Palavras-chave: dc.subjectCompostos organofosforados-
Palavras-chave: dc.subjectInterações eletrostáticas-
Título: dc.titleTheoretical and X-Ray evidence of electrostatic phosphonium anti and gauche effects-
Tipo de arquivo: dc.typeArtigo-
Aparece nas coleções:Repositório Institucional da Universidade Federal de Lavras (RIUFLA)

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