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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 DewhurstThe 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 JournalISSN
1521-3765Publisher
WILEY-VCH Verlag GmbH & Co. KGaA, WeinheimExternal DOI
Volume
21Page range
16968-16974Department affiliated with
- Chemistry Publications
Full text available
- No
Peer reviewed?
- Yes
Legacy Posted Date
2015-10-02Usage metrics
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