Please use this identifier to cite or link to this item:
Type: Artigo de periódico
Title: Stereoelectronic Interactions and the One-Bond C-F Coupling Constant in Sevoflurane
Author: Freitas, MP
Buhl, M
O'Hagan, D
Cormanich, RA
Tormena, CF
Abstract: 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 (n(O) --> sigma(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 (1)J(CF) coupling constants do not appear to be dominated by hyperconjugation; again, dipolar interactions are invoked instead.
Country: EUA
Editor: Amer Chemical Soc
Citation: Journal Of Physical Chemistry A. Amer Chemical Soc, v. 116, n. 6, n. 1677, n. 1682, 2012.
Rights: fechado
Identifier DOI: 10.1021/jp211949m
Date Issue: 2012
Appears in Collections:Unicamp - Artigos e Outros Documentos

Files in This Item:
File Description SizeFormat 
WOS000300277700021.pdf2.57 MBAdobe PDFView/Open

Items in DSpace are protected by copyright, with all rights reserved, unless otherwise indicated.