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

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


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.

Acceptance Date Mar 27, 2018
Publication Date Apr 18, 2018
Publicly Available Date Mar 29, 2024
Journal RSC Advances
Print ISSN 2046-2069
Publisher Royal Society of Chemistry
Pages 14833 - 14837
DOI https://doi.org/10.1039/C8RA02526F
Publisher URL http://dx.doi.org/10.1039/C8RA02526F

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