Hyperconjugation Is the Source of Helicity in Perfluorinated n-Alkanes.

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 σCC →σ*CF interactions are the underlying driving force for the origin of the observed helicity in perfluoroalkanes.