Issue 27, 2018, Issue in Progress
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RSC Advances

The influence of substituent field and resonance effects on the ease of N-heterocyclic carbene formation from imidazolium rings†

Wojciech P. Oziminski ORCID logo *ab  and  Christopher A. Ramsden ORCID logo *c  

* Corresponding authors

a National Medicines Institute, 30/34 Chełmska Street, 00-725 Warsaw, Poland

b Faculty of Pharmacy, Medical University of Warsaw, 1 Banacha Street, 02-097 Warsaw, Poland

c School of Chemical and Physical Sciences, Lennard-Jones Laboratories, Keele University, Staffordshire ST5 5BG, UK
E-mail: c.a.ramsden@keele.ac.uk, wojozim@gmail.com

Abstract

Using a set of twelve selected substituents, the influence of substituent properties on the ease of deprotonation of imidazolium cations and mesoionic imidazolium-4-olates measured by the CREF index has been investigated. Significant correlations between CREF values and the Swain and Lupton field (F) and resonance (R) substituent constants have been found. In all cases the field effect has the greatest influence but resonance effects are also significant.

Graphical abstract: The influence of substituent field and resonance effects on the ease of N-heterocyclic carbene formation from imidazolium rings

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Article information

DOI
https://doi.org/10.1039/C8RA02526F
Article type
Paper
Submitted
22 Mar 2018
Accepted
27 Mar 2018
First published
18 Apr 2018
This article is Open Access
Creative Commons BY-NC license

RSC Adv., 2018,8, 14833-14837

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The influence of substituent field and resonance effects on the ease of N-heterocyclic carbene formation from imidazolium rings

W. P. Oziminski and C. A. Ramsden, RSC Adv., 2018, 8, 14833 DOI: 10.1039/C8RA02526F

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