3 years ago

Hyperconjugation is the Source of Helicity in Perfluorinated n-Alkanes

Hyperconjugation is the Source of Helicity in Perfluorinated n-Alkanes
David O'Hagan, Michael Bühl, Rodrigo A. Cormanich
Hyperconjugative, steric, and electrostatic effects were evaluated as possible sources of the helicity in linear perfluorinated alkanes through analysis of natural bond orbitals and classical electrostatics. Contrary to previous rationalizations, which indicate dominating steric or electrostatic effects, this analysis indicates that hyperconjugative stabilization through σCCσ*CF interactions are the underlying driving force for the origin of the observed helicity in perfluoroalkanes. Hype and twist: It is hyperconjugation (i.e. quantum mechanics), not simple electrostatics, that dictates the helical shape of perfluoroalkanes. This conclusion is contrary to previous rationalizations, which indicate dominating steric or electrostatic effects.

Publisher URL: http://onlinelibrary.wiley.com/resolve/doi

DOI: 10.1002/anie.201704112

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