Twisting the arm: structural constraints in bicyclic expanded-ring N-heterocyclic carbenes

Sampford, Katharine R., Carden, Jamie L., Kidner, Edward B., Berry, Abigail, Cavell, Kingsley J., Murphy, Damien M. ORCID: https://orcid.org/0000-0002-5941-4879, Kariuki, Benson M. ORCID: https://orcid.org/0000-0002-8658-3897 and Newman, Paul D. ORCID: https://orcid.org/0000-0002-1808-1211 2019. Twisting the arm: structural constraints in bicyclic expanded-ring N-heterocyclic carbenes. Dalton Transactions , -. 10.1039/C8DT04462G

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Abstract

A series of diaryl, mono-aryl/alkyl and dialkyl mono- and bicyclic expanded-ring N-heterocyclic carbenes (ER-NHCs) have been prepared and their complexation to Au(I) investigated through the structural analysis of fifteen Au(NHC)X and/or [Au(NHC)2]X complexes. The substituted diaryl 7-NHCs are the most sterically encumbered with large buried volume (%VB) values of 40–50% with the less flexible six-membered analogues having %VB values at least 5% smaller. Although the bicyclic systems containing fused 6- and 7-membered rings (6,7-NHCs) are constrained with relatively acute NCN bond angles, they have the largest %VB values of the dialkyl derivatives reported here, a feature related to the fixed conformation of the heterocyclic rings and the compressional effect of a pre-set methyl substituent.

Item Type:	Article
Date Type:	Published Online
Status:	Published
Schools:	Chemistry
Publisher:	Royal Society of Chemistry
ISSN:	1477-9226
Funders:	EPSRC
Date of First Compliant Deposit:	22 January 2019
Date of Acceptance:	10 December 2018
Last Modified:	21 May 2023 21:53
URI:	https://orca.cardiff.ac.uk/id/eprint/118606

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