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Identification of a lead candidate in the search for carbene-stabilized homoaromatics

Version 2 2023-09-05, 13:39
Version 1 2023-06-08, 22:11
journal contribution
posted on 2023-09-05, 13:39 authored by James D Mattock, Alfredo VargasAlfredo Vargas, Rian D Dewhurst
The effect of carbenes as Lewis donor groups on the homoaromaticity of mono- and bicyclic organic molecules is surveyed. The search for viable carbene-stabilized homoaromatics resulted in a large amount of rejected candidates as well as nine promising candidates that are further analyzed for their homoaromaticity using a number of metrics. Of these, five appeared to show modest homoaromaticity, while 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-stabilized homoaromatics are discussed.

History

Publication status

  • Published

Journal

Chemistry - A European Journal

ISSN

1521-3765

Publisher

WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim

Volume

21

Page range

16968-16974

Department affiliated with

  • Chemistry Publications

Full text available

  • No

Peer reviewed?

  • Yes

Legacy Posted Date

2015-10-02

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