Issue 86, 2022

Stability of alkyl carbocations


The traditional and widespread rationale behind the stability trend of alkyl-substituted carbocations is incomplete. Through state-of-the-art quantum chemical analyses, we quantitatively established a generally overlooked driving force behind the stability of carbocations, namely, that the parent substrates are substantially destabilized by the introduction of substituents, often playing a dominant role in solution. This stems from the repulsion between the substituents and the C–X bond.

Graphical abstract: Stability of alkyl carbocations

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Article information

Article type
19 Jul 2022
06 Oct 2022
First published
06 Oct 2022
This article is Open Access
Creative Commons BY license

Chem. Commun., 2022,58, 12050-12053

Stability of alkyl carbocations

T. Hansen, P. Vermeeren, F. M. Bickelhaupt and T. A. Hamlin, Chem. Commun., 2022, 58, 12050 DOI: 10.1039/D2CC04034D

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