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

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) anio...

Full description

Saved in:
Bibliographic Details
Published in:Journal of organic chemistry 2017-12, Vol.82 (23), p.12485-12491
Main Authors: Ramsden, Christopher A, Oziminski, Wojciech P
Format: Article
Language:English
Citations: Items that this one cites
Items that cite this one
Online Access:Get full text
Tags: Add Tag
No Tags, Be the first to tag this record!
Description
Summary: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.
ISSN:0022-3263
1520-6904
DOI:10.1021/acs.joc.7b02283