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Título: | Solution conformations for the flexible 1-chloro-1,1-difluoro-2-pentanol unveiled using multinuclear magnetic resonance |
Palavras-chave: | Conformation analysis Nuclear magnetic resonance Coupling constant Intramolecular interactions Solvent effect |
Data do documento: | Fev-2018 |
Editor: | Elsevier |
Citação: | MARTINS, F. A. et al. Solution conformations for the flexible 1-chloro-1,1-difluoro-2-pentanol unveiled using multinuclear magnetic resonance. Tetrahedron, [S.l.], v. 74, n. 8, p. 880-883, Feb. 2018. |
Resumo: | The 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. |
URI: | https://www.sciencedirect.com/science/article/pii/S0040402018300206 http://repositorio.ufla.br/jspui/handle/1/34480 |
Aparece nas coleções: | DQI - Artigos publicados em periódicos |
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