Double axial stabilization of a carbenium ion via convergent PO → C+ tetrel bonding

Elishua D. Litle; François P. Gabbaï

doi:10.1039/D3CC04729F

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Double axial stabilization of a carbenium ion via convergent PO → C⁺ tetrel bonding†

Elishua D. Litle

^a and François P. Gabbaï

*^a

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* Corresponding authors

^a Department of Chemistry, Texas A&M University, College Station, TX 77843, USA
E-mail: francois@tamu.edu

Abstract

Our efforts in carbocation chemistry have led us to target examples of such species stabilized intramolecularly by tetrel bonding. Described here is an example of such a compound in which a triaryl carbenium is stabilized intramolecularly by two convergent P [double bond, length as m-dash] O → C_carbenium interactions, as confirmed by structural studies. The formation of this new motif favorably impacts the reversibility of the first and second reduction of the carbenium center. It also has profound influence on the Lewis acidity of the carbenium center which is lower than that of the unsubstituted parent carbenium by seven orders of magnitude.

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Article information

DOI: https://doi.org/10.1039/D3CC04729F
Article type: Communication
Submitted: 22 Sep 2023
Accepted: 07 Dec 2023
First published: 08 Dec 2023

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Chem. Commun., 2024,60, 690-693

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Double axial stabilization of a carbenium ion via convergent PO → C⁺ tetrel bonding

E. D. Litle and F. P. Gabbaï, Chem. Commun., 2024, 60, 690 DOI: 10.1039/D3CC04729F

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