Schiff base

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A Schiff base (or azomethine), named after Hugo Schiff, is a functional group that contains a carbon-nitrogen double bond with the nitrogen atom connected to an aryl or alkyl group—but not hydrogen ^[1]. Schiff bases are of the general formula R₁R₂C=N-R₃, where R₃ is an aryl or alkyl group that makes the Schiff base a stable imine. A Schiff base derived from an aniline, where R₃ is a phenyl or substituted phenyl, can be called an anil.^[1]

Schiff bases can be synthesized from an aromatic amine and a carbonyl compound by nucleophilic addition forming a hemiaminal, followed by a dehydration to generate an imine. In a typical reaction, 4,4'-diaminodiphenyl ether reacts with o-vanillin:^[1]

There is a Schiff base intermediate in the fructose 1,6-bisphosphate aldolase catalyzed reaction during glycolysis.

References

de:Schiffsche Base

fr:Imine it:Immine he:אימין mk:Имин mk:Шифова база ja:イミンsv:Imin

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