Conformational analysis of 2,2-difluoroethylamine hydrochloride: double gauche effect

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MetadadosDescriçãoIdioma
Autor(es): dc.creatorSilla, Josué M.-
Autor(es): dc.creatorDuarte, Claudimar J.-
Autor(es): dc.creatorCormanich, Rodrigo A.-
Autor(es): dc.creatorRittner, Roberto-
Autor(es): dc.creatorFreitas, Matheus P.-
Data de aceite: dc.date.accessioned2026-02-09T11:43:35Z-
Data de disponibilização: dc.date.available2026-02-09T11:43:35Z-
Data de envio: dc.date.issued2020-07-12-
Data de envio: dc.date.issued2020-07-12-
Data de envio: dc.date.issued2014-04-16-
Fonte completa do material: dc.identifierhttps://repositorio.ufla.br/handle/1/41840-
Fonte: dc.identifier.urihttp://educapes.capes.gov.br/handle/capes/1146093-
Descrição: dc.descriptionThe gauche effect in fluorinated alkylammonium salts is well known and attributed either to an intramolecular hydrogen bond or to an electrostatic attraction between the positively charged nitrogen and the vicinal electronegative fluorine atom. This work reports the effect of adding a fluorine atom in 2-fluoroethylamine hydrochloride on the conformational isomerism of the resulting 2,2-difluoroethylamine chloride (2). The analysis was carried out using NMR coupling constants in D2O solution, in order to mimic the equilibrium conditions in a physiological medium, in the gas phase and in implicit water through theoretical calculations. Despite the presence of σCH→σ*CF and σCH→σ*CN interactions, which usually rule the hyperconjugative gauche effect in 1,2-disubstituted ethanes, the most important forces leading to the double gauche effect (+NH3 in the gauche relationship with both fluorine atoms) in 2 are the Lewis-type ones. Particularly, electrostatic interactions are operative even in water solution, where they should be significantly attenuated, whereas hyperconjugation and hydrogen bond have secondary importance.-
Formato: dc.formatapplication/pdf-
Idioma: dc.languageen-
Publicador: dc.publisherBeilstein-Institut-
Direitos: dc.rightsAttribution 4.0 International-
Direitos: dc.rightsAttribution 4.0 International-
Direitos: dc.rightsacesso aberto-
Direitos: dc.rightshttp://creativecommons.org/licenses/by/4.0/-
Direitos: dc.rightshttp://creativecommons.org/licenses/by/4.0/-
???dc.source???: dc.sourceBeilstein Journal of Organic Chemistry-
Palavras-chave: dc.subjectConformational analysis-
Palavras-chave: dc.subject2,2-difluoroethylamine hydrochloride-
Palavras-chave: dc.subjectGauche effect-
Palavras-chave: dc.subjectHydrogen bonding-
Título: dc.titleConformational analysis of 2,2-difluoroethylamine hydrochloride: double gauche effect-
Tipo de arquivo: dc.typeArtigo-
Aparece nas coleções:Repositório Institucional da Universidade Federal de Lavras (RIUFLA)

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