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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. 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. 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]
A mixture of 4,4'-diaminodiphenyl ether 1 (1.00 g, 5.00 mmol) and o-vanillin 2 (1.52 g , 10.00 mmol) in methanol (40.00 mL) is stirred at room temperature for one hour to give an orange precipitate and after filtration and washing with methanol to give the pure Schiff base 3 (2.27 g, 97.00%)
There is a Schiff base intermediate in the fructose 1,6-bisphosphate aldolase catalyzed reaction during glycolysis.
- International Union of Pure and Applied Chemistry. "Schiff base". Compendium of Chemical Terminology Internet edition.
- ^ 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.