A Quantitative Analysis of Factors Influencing Ease of Formation and s-Bonding Strength of Oxa- and Thia-N-Heterocyclic Carbenes

Abstract

The index described previously (carbene relative energy of formation) has been extended to oxygen and sulfur heterocycles. This provides a quantitative overview of factors determining ease of formation of (i) neutral N-heterocyclic carbenes (NHCs) by deprotonation of heterocyclic salts and (ii) anionic NHCs by deprotonation of heterocyclic mesomeric betaines. The influence of the nature and ring position of oxygen and sulfur is discussed for a range of known and unknown systems. Attention is directed to unexplored systems of potential interest.

Citation

(2017). A Quantitative Analysis of Factors Influencing Ease of Formation and s-Bonding Strength of Oxa- and Thia-N-Heterocyclic Carbenes. Journal of Organic Chemistry, https://doi.org/10.1021/acs.joc.7b02283

• Acceptance Date: Oct 20, 2017
• Publication Date: Oct 20, 2017
• Journal: Journal of Organic Chemistry
• Print ISSN: 0022-3263
• Publisher: American Chemical Society
• DOI: https://doi.org/10.1021/acs.joc.7b02283
• Publisher URL: https://pubs.acs.org/doi/10.1021/acs.joc.7b02283