imidine

File:Cyclic imidine.png

In chemistry imidines are a rare functional group, being the nitrogen analogues of anhydrides and imides. They were first reported by Adolf Pinner in 1883,{{cite journal |last1=Pinner |first1=A. |title=Ueber die Umwandlung der Nitrile in Imide. Verhalten der Blausäure und des Aethylencyanids gegen Salzsäure und Alkohol |journal=Berichte der Deutschen Chemischen Gesellschaft |date=January 1883 |volume=16 |issue=1 |pages=352–363 |doi=10.1002/cber.18830160187}} but did not see significant investigation until the 1950s, when Patrick Linstead and John Arthur Elvidge developed a number of compounds.{{cite journal |last1=Elvidge |first1=J. A. |last2=Linstead |first2=R. P. |title=Heterocyclic imines and amines. Part III. Succinimidine |journal=Journal of the Chemical Society (Resumed) |date=1954 |pages=442 |doi=10.1039/JR9540000442}}{{cite journal |last1=Elvidge |first1=J. A. |last2=Linstead |first2=R. P. |last3=Salaman |first3=Ann M. |title=37. Heterocyclic imines and amines. Part IX. Glutarimidine and the imidine from α-phenylglutaronitrile |journal=J. Chem. Soc. |date=1959 |pages=208–215 | doi=10.1039/JR9590000208}}

Imidines may be prepared in a modified Pinner reaction, by passing hydrogen chloride into an alcoholic solution of their corresponding di-nitriles (i.e. succinonitrile, glutaronitrile, adiponitrile) to give imino ethers which then condense when treated with ammonia. As a result, most structures are cyclic.

The compounds are highly moisture sensitive and can be converted into imides upon exposure to water.