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A Schiff base, or Schiff's base, is a functional group or type of chemical compound containing a carbon-nitrogen double bond with the nitrogen atom connected to an aryl group or an alkyl group but not hydrogen. The Schiff base is synonymous with an azomethine. The Schiff base is named after Hugo Schiff and has the following general structure:
R1R2C=N-R3
R3 stands for a phenyl or alkyl group which makes the Schiff base a stable imine. Schiff bases can be synthesized from an aromatic amine and a carbonyl compound by nucleophilic addition forming a hemiaminal, followed by dehydration to generate the imine. In a typical reaction, 4,4'-diaminodiphenyl ether reacts with o-vanillin:
There is a Schiff base intermediate in the fructose 1,6-bisphosphate aldolase catalyzed reaction during glycolysis.
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