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metadata.artigo.dc.title: Solution conformations for the flexible 1-chloro-1,1-difluoro-2-pentanol unveiled using multinuclear magnetic resonance
metadata.artigo.dc.creator: Martins, Francisco A.
Zeoly, Lucas A.
Cormanich, Rodrigo A.
Freitas, Matheus P.
metadata.artigo.dc.subject: Conformation analysis
Nuclear magnetic resonance
Coupling constant
Intramolecular interactions
Solvent effect
metadata.artigo.dc.publisher: Elsevier Feb-2018
metadata.artigo.dc.identifier.citation: 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.
metadata.artigo.dc.description.abstract: 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.
metadata.artigo.dc.language: en_US
Appears in Collections:DQI - Artigos publicados em periódicos

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