Negative fluorine hyperconjugation. A theoretical re-examination
- 1 January 1981
- journal article
- research article
- Published by Royal Society of Chemistry (RSC) in Journal of the Chemical Society, Chemical Communications
- No. 9,p. 396-398
- https://doi.org/10.1039/c39810000396
Abstract
Molecular orbital ab initio calculations show that the small changes in hydrocarbon acidities or in the rates of nucleophilic substitution reactions, which are found whan a β-F is substituted by a β-CF3 group, do not reflect absence of fluorine hyperconjugation, but result from the stronger inductive effect of the CF3 group relative to F, which compensates for its poorer hyperconjugation.Keywords
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