pKas of the conjugate acids of N-heterocyclic carbenes in water

Eleanor M Higgins; Jennifer A Sherwood; Anita G Lindsay; James Armstrong; Richard S Massey; Roger W Alder; AnnMarie C O'Donoghue

doi:10.1039/c0cc03367g

pKas of the conjugate acids of N-heterocyclic carbenes in water

Chem Commun (Camb). 2011 Feb 7;47(5):1559-61. doi: 10.1039/c0cc03367g. Epub 2010 Nov 29.

Authors

Eleanor M Higgins¹, Jennifer A Sherwood, Anita G Lindsay, James Armstrong, Richard S Massey, Roger W Alder, AnnMarie C O'Donoghue

Affiliation

¹ Department of Chemistry, University Science Laboratories, South Road, Durham DH1 3LE, UK.

PMID: 21116519
DOI: 10.1039/c0cc03367g

Abstract

pK(a) values of 19.8-28.2 are reported for the conjugate acids of a large series of NHCs in water. The effects of ring size, N-substituent and C(4)-C(5) saturation on pK(a) are discussed.