Use este identificador para citar ou linkar para este item: http://repositorio.ufla.br/jspui/handle/1/41819
Título: Stereoelectronic interactions and the one-bond C-F coupling constant in sevoflurane
Palavras-chave: Molecular properties
Solvents
Molecular structure
Molecular interactions
Gases
Data do documento: Jan-2012
Editor: American Chemical Society (ACS)
Citação: FREITAS, M. P. et al. Stereoelectronic interactions and the one-bond C-F coupling constant in sevoflurane. The Journal of Physical Chemistry A, [S.l.], v. 116, n. 6, p. 1677-1682, Jan. 2012. DOI: 10.1021/jp211949m.
Resumo: The conformational preference of the widely utilized anesthetic fluoromethyl-1,1,1,3,3,3-hexafluoro-2-propyl ether (sevoflurane) has been investigated computationally and by NMR spectroscopy. Three conformational minima were located at the B3LYP/aug-cc-pVDZ level, but one is significantly more stable (by ca. 4 kcal/mol) than the other two. This is the case both for gas phase calculations and for solution NMR data. Although the main conformer is stabilized by electron delocalization (nO → σ*C–F), this type of hyperconjugation was not found to be the main driver for the conformer stabilization in the gas phase and, consequently, for the apparent anomeric effect in sevoflurane. Instead, more classical steric and electrostatic interactions appear to be responsible for the conformational energies. Also the 1JCF coupling constants do not appear to be dominated by hyperconjugation; again, dipolar interactions are invoked instead.
URI: https://pubs.acs.org/doi/10.1021/jp211949m
http://repositorio.ufla.br/jspui/handle/1/41819
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