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.
Y. Apeloig, J. Chem. Soc., Chem. Commun., 1981, 396 DOI: 10.1039/C39810000396
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