Nitrilimine

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.

Nitrilimines were first observed in the thermal decomposition of 2-tetrazoles releasing nitrogen:[1] Nitrilimines are linear 1,3-dipoles represented by structures 1 and 3.

Due to their high energy, they are usually generated in situ as a reactive intermediate.