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Hyperconjugation Is the Source of Helicity in Perfluorinated n ‐Alkanes
Author(s) -
Cormanich Rodrigo A.,
O'Hagan David,
Bühl Michael
Publication year - 2017
Publication title -
angewandte chemie
Language(s) - English
Resource type - Journals
eISSN - 1521-3757
pISSN - 0044-8249
DOI - 10.1002/ange.201704112
Subject(s) - hyperconjugation , helicity , steric effects , chemistry , computational chemistry , electrostatics , atomic orbital , chemical physics , organic chemistry , molecule , physics , quantum mechanics , electron
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 σ CC →σ* CF interactions are the underlying driving force for the origin of the observed helicity in perfluoroalkanes.