Persistent carbene
A persistent carbene (also known as stable carbene) is an organic molecule whose natural resonance structure has a carbon atom with incomplete octet (a carbene), but does not exhibit the tremendous instability typically associated with such moieties. The best-known examples and by far largest subgroup are the N-heterocyclic carbenes (NHC) (sometimes called Arduengo carbenes), in which nitrogen atoms flank the formal carbene.