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Journal Articles Chemistry - A European Journal Year : 2014

Large Hyperconjugation in Strained Systems

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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).

Dates and versions

hal-01347475 , version 1 (21-07-2016)

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

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