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Large Hyperconjugation in Strained Systems

Abstract : Carbocations can appear as transient species, for instance, in elimination reactions and various rearrangements. Hyperconjugation (or conjugation) can then stabilize the cationic character and form a partial π bond. The effect of the electronic delocalization from strained substituents to a carbocation part was calculated. Very large hyperconjugation was found, sometimes more than 80 kcal mol-1, which is much larger than typical conjugation effects (56 kcal mol-1 for the allyl cation).
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Contributor : Stephane Humbel <>
Submitted on : Thursday, July 21, 2016 - 10:13:17 AM
Last modification on : Thursday, January 23, 2020 - 6:22:05 PM

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Julien Racine, Stéphane Humbel. Large Hyperconjugation in Strained Systems. Chemistry - A European Journal, Wiley-VCH Verlag, 2014, Chemistry a European Journal, 20, pp.12601-12606. ⟨10.1002/chem.201403582⟩. ⟨hal-01347475⟩



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