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

You do not have JavaScript enabled. Please enable JavaScript to access the full features of the site or access our non-JavaScript page.

pK_as of the conjugate acids of N-heterocyclic carbenes in water†

Eleanor M. Higgins,^a Jennifer A. Sherwood,^b Anita G. Lindsay,^a James Armstrong,^a Richard S. Massey,^a Roger W. Alder^c and AnnMarie C. O'Donoghue*^a

Author affiliations

* Corresponding authors

^a Department of Chemistry, University Science Laboratories, South Road, Durham DH1 3LE, UK
E-mail: annmarie.odonoghue@durham.ac.uk

^b The School of Chemistry and Chemical Biology, University College Dublin, Belfield, Dublin 4, Ireland

^c The School of Chemistry, University of Bristol, Bristol BS8 1TS, UK

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.

Download options Please wait...

Supplementary files

Experimental procedures and kinetic data PDF (6773K)

Article information

DOI: https://doi.org/10.1039/C0CC03367G
Article type: Communication
Submitted: 19 Aug 2010
Accepted: 11 Nov 2010
First published: 29 Nov 2010

Download Citation

Chem. Commun., 2011,47, 1559-1561

Permissions

Request permissions

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

E. M. Higgins, J. A. Sherwood, A. G. Lindsay, J. Armstrong, R. S. Massey, R. W. Alder and A. C. O'Donoghue, Chem. Commun., 2011, 47, 1559 DOI: 10.1039/C0CC03367G

To request permission to reproduce material from this article, please go to the Copyright Clearance Center request page.

If you are an author contributing to an RSC publication, you do not need to request permission provided correct acknowledgement is given.

If you are the author of this article, you do not need to request permission to reproduce figures and diagrams provided correct acknowledgement is given. If you want to reproduce the whole article in a third-party publication (excluding your thesis/dissertation for which permission is not required) please go to the Copyright Clearance Center request page.

Social activity

Fetching data from CrossRef.
This may take some time to load.

Chemical Communications