nitrilimine
Sign in to saveAlso known as nitrilimines, nitrile amide, nitrile amides, nitrile imine
Nitrilimines or nitrile amides are a class of organic compounds sharing a common functional group with the general structure 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 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 , allene-like , allylic and carbene are of lesser relevance. {| style="margin-left: auto; margin-right: aut
~1 min read
Encyclopedic overview
1 sectionsContents
- References
Nitrilimines or nitrile amides are a class of organic compounds sharing a common functional group with the general structure 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 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 , allene-like , allylic and carbene are of lesser relevance. {| style="margin-left: auto; margin-right: auto; border: none; text-align:center;" |\ce{H-\!{\equiv}}{\color{Blue}\ce{N+}}\!{-}\!{\color{Red}\ce{N-}}\!{-}\!{\color{Red}\ce H}|| |H-\!{\equiv}N=N-H|| |\ce H\!{-}\!{\color{Red} \ce{C-}}\!{=}{\color{Blue}\ce{N+}}\!\ce{=N-H}|| |\ce H\!{-}\!{\color{Blue} \ce{C+}}\!\ce{=N}\!{-}\!{\color{Red}\ce{N-}}\!\ce{-H}|| |H-C{:}\!-N=N-H |}
Nitrilimines were first observed in the thermal decomposition of 2-tetrazoles releasing nitrogen:
Excerpted from Wikipedia’s “nitrilimine” article, available under the CC BY-SA 4.0 licence.