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Updated: Apr 1, 2026

Isolating Free Carbenes, their Mixed Dimers and Organic Radicals
Published on: April 19, 2019
Identification of a Lead Candidate in the Search for Carbene-Stabilised Homoaromatics
James D Mattock1, Alfredo Vargas2, Rian D Dewhurst3
1Department of Chemistry, School of Life Sciences, University of Sussex, Brighton BN1 9QJ, Sussex (UK) http://www.sussex.ac.uk/lifesci/vargaslab.
Abstract:
The effect of carbenes as Lewis donor groups on the homoaromaticity of mono- and bicyclic organic molecules is surveyed. The search for viable carbene-stabilised homoaromatics resulted in a large amount of rejected candidates as well as nine promising candidates that are further analysed for their homoaromaticity by using a number of metrics. Of these, five appeared to show modest homoaromaticity, whereas another compound showed a level of homoaromaticity comparable with the homotropylium cation benchmark compound. Isoelectronic analogues and constitutional isomers of the lead compound were investigated, however, none of these showed comparable homoaromaticity. The implications of these calculations on the design of donor-stabilised homoaromatics are discussed.
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