Solution conformations for the flexible 1-chloro-1,1-difluoro-2-pentanol unveiled using multinuclear magnetic resonance

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MetadadosDescriçãoIdioma
Autor(es): dc.creatorMartins, Francisco A.-
Autor(es): dc.creatorZeoly, Lucas A.-
Autor(es): dc.creatorCormanich, Rodrigo A.-
Autor(es): dc.creatorFreitas, Matheus P.-
Data de aceite: dc.date.accessioned2026-02-09T12:51:06Z-
Data de disponibilização: dc.date.available2026-02-09T12:51:06Z-
Data de envio: dc.date.issued2019-05-31-
Data de envio: dc.date.issued2019-05-31-
Data de envio: dc.date.issued2018-02-
Fonte completa do material: dc.identifierhttps://repositorio.ufla.br/handle/1/34480-
Fonte completa do material: dc.identifierhttps://www.sciencedirect.com/science/article/pii/S0040402018300206-
Fonte: dc.identifier.urihttp://educapes.capes.gov.br/handle/capes/1169513-
Descrição: dc.descriptionThe preferred conformations of a small polyfunctional molecule containing fluorine, chlorine and hydroxyl groups, the 1-chloro-1,1-difluoro-2-pentanol (CDP), were completely elucidated using 1H, 13C and 19F NMR in three different solvents. While the Cl-C-C-O dihedral angle was asserted using coupling constant data for the diastereotopic fluorines, the Et-C-C-O torsional angle was analyzed by means of 1H NMR spectra with selective irradiation of the diastereotopic hydrogens and fluorines. In addition, unusual couplings of the hydroxyl hydrogen with a diastereotopic hydrogen and fluorines provided information on the O-H orientation. The behavior of 1JC,F when the solvents varied agrees with a weak F⋅⋅⋅HO intramolecular hydrogen bond. These findings were corroborated, and the governing interactions rationalized with the aid of high level CCSD(T) theoretical calculations. Noteworthy, hyperconjugation involving the electron-acceptor σ*C-Cl orbital drives the conformational equilibrium rather than the fluorine gauche effect.-
Idioma: dc.languageen-
Publicador: dc.publisherElsevier-
Direitos: dc.rightsrestrictAccess-
???dc.source???: dc.sourceTetrahedron-
Palavras-chave: dc.subjectConformation analysis-
Palavras-chave: dc.subjectNuclear magnetic resonance-
Palavras-chave: dc.subjectCoupling constant-
Palavras-chave: dc.subjectIntramolecular interactions-
Palavras-chave: dc.subjectSolvent effect-
Título: dc.titleSolution conformations for the flexible 1-chloro-1,1-difluoro-2-pentanol unveiled using multinuclear magnetic resonance-
Tipo de arquivo: dc.typeArtigo-
Aparece nas coleções:Repositório Institucional da Universidade Federal de Lavras (RIUFLA)

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