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Quantitative Index of the Relative Ease of Formation and s-Bonding Strength of N-Heterocyclic Carbenes

Abstract

An energy-based index of the ease of N-heterocyclic carbene (NHC) formation either by deprotonation of precursor salts to give neutral NHCs or deprotonation of heterocyclic mesomeric betaines to give anionic NHCs is described. This index (CREF; Carbene Relative Energy of Formation), which is easily calculated using DFT methods, also gives a quantitative measure of the relative s-donor strength of NHCs. CREF index values for a wide range of known and unknown NHC ring systems are reported and their significance discussed.

Acceptance Date Jul 1, 2016
Publication Date Jul 1, 2016
Journal The Journal of Organic Chemistry
Print ISSN 0022-3263
Publisher American Chemical Society
Pages 10295 - 10301
DOI https://doi.org/10.1021/acs.joc.6b01304
Publisher URL https://pubs.acs.org/doi/10.1021/acs.joc.6b01304

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