Quantifying and understanding the electronic properties of N-heterocyclic carbenes

The use of N -heterocyclic carbenes (NHCs) in chemistry has developed rapidly over the past twenty years. These interesting compounds are predominantly employed in organometallic chemistry as ligands for various metal centres, and as organocatalysts able to mediate an exciting range of reactions. However, the sheer number of NHCs known in the literature can make the appropriate choice of NHC for a given application difficult. A number of metrics have been explored that allow the electronic properties of NHCs to be quantified and compared. In this review, we discuss these various metrics and what they can teach about the electronic properties of NHCs. Data for approximately three hundred NHCs are presented, obtained from a detailed survey of the literature. The wide range of NHCs known in the literature can make choosing an NHC for a given application difficult. In this review, the electronic properties of NHCs are discussed, as well as the various methods by which they can be quantified. Data for ca. three hundred NHCs are provided.