Schiff base
From Free net encyclopedia
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 a aryl group or an alkyl group but not hydrogen. The Schiff base is named after Hugo Schiff.
- R1R2C=N-R3
R3 stands for a phenyl or alkyl group which makes the Schiff base a stable imine. Schiff bases can be synthesised from an aromatic amine and a carbonyl compound in a nucleophilic addition to a hemiaminal followed elimination of water to the imine. The Schiff base is synonymous with an azomethine. 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.
Schiff Bases are also the punchline in many chemistry jokes. Take the past tense of imine synthesis: with the addition of ethanol, the reaction mixture became schiff based.
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References
- [1] Synthesis of 2-({[4-(4-{[(E)-1-(2-hydroxy-3-methoxyphenyl) methylidene]amino}phenoxy)phenyl]imino}methyl)- 6 -methoxy phenol A. A. jarrahpour, M. Zarei Molbank 2004, M352 [1] open access publication.de: Schiffsche Base