Stereoelectronic Interactions and the One-Bond C-F Coupling Constant in Sevoflurane

Matheus P. Freitas, Michael Buehl, David O'Hagan, Rodrigo A. Cormanich, Claudio F. Tormena

Research output: Contribution to journalArticlepeer-review

27 Citations (Scopus)


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.

Original languageEnglish
Pages (from-to)1677-1682
Number of pages6
JournalJournal of Physical Chemistry A
Issue number6
Publication statusPublished - 16 Feb 2012


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