Simultaneous gauche and anomeric effects in alpha-substituted sulfoxides

Registro completo de metadados
MetadadosDescriçãoIdioma
Autor(es): dc.creatorFreitas, Matheus P.-
Data de aceite: dc.date.accessioned2026-02-09T12:44:16Z-
Data de disponibilização: dc.date.available2026-02-09T12:44:16Z-
Data de envio: dc.date.issued2020-07-12-
Data de envio: dc.date.issued2020-07-12-
Data de envio: dc.date.issued2012-08-10-
Fonte completa do material: dc.identifierhttps://repositorio.ufla.br/handle/1/41825-
Fonte completa do material: dc.identifierhttps://pubs.acs.org/doi/10.1021/jo3014885-
Fonte: dc.identifier.urihttp://educapes.capes.gov.br/handle/capes/1167272-
Descrição: dc.descriptionα-Substituted sulfoxides can experience both gauche and anomeric effects, since these compounds have the geometric requirements and strong electron donor and acceptor orbitals which are essential to make operative the hyperconjugative nature of these effects. Indeed, the title effects were calculated to take place for 1,3-oxathiane 3-oxide in polar solution, where dipolar effects are absent or at least minimized, while only the gauche effect is present in 2-fluorothiane 1-oxide. Since the fluorine atom is a suitable probe for structural analysis using NMR, the 1JCF dependence on the rotation around the F–C–S═O dihedral angle of (fluoromethyl)methyl sulfoxide was evaluated; differently from 1,2-difluoroethane and fluoro(methoxy)methane, this coupling constant is at least not exclusively dependent on dipolar interactions (or on hyperconjugation). Because of the nonmonotonic behavior of the 1JCF rotational profile, this coupling constant does not appear to be of significant diagnostic value for probing the conformations of α-fluoro sulfoxides.-
Idioma: dc.languageen-
Publicador: dc.publisherAmerican Chemical Society (ACS)-
Direitos: dc.rightsrestrictAccess-
???dc.source???: dc.sourceJournal of Organic Chemistry (JOC)-
Palavras-chave: dc.subjectOxides-
Palavras-chave: dc.subjectMolecular properties-
Palavras-chave: dc.subjectEnergy-
Palavras-chave: dc.subjectConformation-
Palavras-chave: dc.subjectMolecular structure-
Título: dc.titleSimultaneous gauche and anomeric effects in alpha-substituted sulfoxides-
Tipo de arquivo: dc.typeArtigo-
Aparece nas coleções:Repositório Institucional da Universidade Federal de Lavras (RIUFLA)

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