Schiff base
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2008-07-06T12:15:19Z
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[[Image:Schiffbase.png|150px|right|Schiff base]]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]] <ref>{{GoldBookRef | title = Schiff base | file = S05498}}</ref>. Schiff bases are of the general formula R<sub>1</sub>R<sub>2</sub>C=N-R<sub>3</sub>, where R<sub>3</sub> is an aryl or alkyl group that makes the Schiff base a stable [[imine]]. A Schiff base derived from an [[aniline]], where R<sub>3</sub> is a [[phenyl]] or substituted phenyl, can be called an ''anil''.<ref>{{GoldBookRef|title=anils|file=A00357}}</ref>
Schiff bases can be synthesized from an [[aromatic]] [[amine]] and a [[carbonyl]] compound by [[nucleophilic addition]] forming a [[hemiaminal]], followed by a [[dehydration reaction|dehydration]] to generate an [[imine]]. In a typical reaction, 4,4'-diaminodiphenyl ether reacts with o-[[vanillin]]:<ref>''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 [http://www.mdpi.net/molbank/molbank2004/m0352.htm] [[open access]] publication.</ref>
[[Image:schiff base.gif|left|frame|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%)]]
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There is a Schiff base intermediate in the [[Aldolase|fructose 1,6-bisphosphate aldolase]] catalyzed reaction during [[glycolysis]].
== References ==
{{Reflist}}
[[Category:functional groups]]
[[de:Schiffsche Base]]
[[fr:Imine]]
[[it:Immine]]
[[he:אימין]]
[[mk:Имин]]
[[mk:Шифова база]]
[[ja:イミン]]
[[pl:Imina]]
[[pt:Base de Schiff]]
[[sv:Imin]]
[[zh:施夫碱]]