Nitrilimines or nitrile amides are a class of organic compounds sharing a common functional group with the general structure R−CN−NR corresponding to the conjugate base of an amine bonded to the N-terminus of a nitrile. The dominant structure for the parent compound nitrilimine is that of the propargyl-like 1 in scheme 1 with a C–N triple bond and with a formal positive charge on nitrogen and two lone pairs and a formal negative charge on the terminal nitrogen. Other structures such as hypervalent 2 , allene-like 3 , allylic 4 and carbene 5 are of lesser relevance.
1 | 2 | 3 | 4 | 5 |
Nitrilimines were first observed in the thermal decomposition of 2-tetrazoles releasing nitrogen: [1]
 | 6 |
Nitrilimines are linear 1,3-dipoles represented by structures 1 and 3 . A major use is in heterocyclic synthesis. E.g. with alkynes they generate pyrazoles in a 1,3-dipolar cycloaddition. Due to their high energy, they are usually generated in situ as a reactive intermediate.