Hyperconjugation is the source of helicity in perfluorinated n-alkanes
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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 rationalisations, which indicate dominating steric or electrostatic effects, this analysis indicates that hyperconjugative stabilisation through σCC-> σ*CF interactions are the underlying driving force for the origin of the observed helicity in perfluoroalkanes
Cormanich , R A , O'Hagan , D & Buehl , M 2017 , ' Hyperconjugation is the source of helicity in perfluorinated n -alkanes ' , Angewandte Chemie International Edition , vol. 56 , no. 27 , pp. 7867-7870 . https://doi.org/10.1002/anie.201704112
Angewandte Chemie International Edition
© 2017 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim. This work has been made available online in accordance with the publisher’s policies. This is the author created, accepted version manuscript following peer review and may differ slightly from the final published version. The final published version of this work is available at: https://doi.org/10.1002/anie.201704112
DescriptionThe authors thank FAPESP and EaStCHEM funding agencies.
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