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Nitrilimine

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.

\ce{H-\!{\equiv}}{\color{Blue}\ce{N+}}\!{-}\!{\color{Red}\ce{N-}}\!{-}\!{\color{Red}\ce H}
2}}3}}4}}5}}

Nitrilimines were first observed in the thermal decomposition of 2-tetrazoles releasing nitrogen:

Nitrilimines are linear 1,3-dipoles represented by structures and . 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.

References

Dead reference:

  1. The electronic structure of nitrilimine: absence of the carbenic form Fausto Cargnoni, Giorgio Molteni, David L. Cooper, Mario Raimondi and Alessandro Ponti Chemical Communications, 2006, 1030 - 1032 Abstract] --

References

  1. (June 1959). "Communications: The Formation of Nitrile Imines in the Thermal Breakdown of 2,5-Disubstituted Tetrazoles". The Journal of Organic Chemistry.
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