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Issue 5, 2019
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Twisting the arm: structural constraints in bicyclic expanded-ring N-heterocyclic carbenes

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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.

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

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Article information


Submitted
09 Nov 2018
Accepted
10 Dec 2018
First published
17 Jan 2019

This article is Open Access

Dalton Trans., 2019,48, 1850-1858
Article type
Paper

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

K. R. Sampford, J. L. Carden, E. B. Kidner, A. Berry, K. J. Cavell, D. M. Murphy, B. M. Kariuki and P. D. Newman, Dalton Trans., 2019, 48, 1850
DOI: 10.1039/C8DT04462G

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