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Schiff base

Not to be confused with Schiff test.
General structure of an imine. Schiff bases are imines in which R3 is an alkyl or aryl group (not a hydrogen). R1 and R2 may be hydrogens
General structure of an azomethine compound

In organic chemistry, a Schiff base (named after Hugo Schiff) is a compound with the general structure R1R2C=NR3 (R3 = alkyl or aryl, but not hydrogen).[1][2] They can be considered a sub-class of imines, being either secondary ketimines or secondary aldimines depending on their structure. Anil refers to a common subset of Schiff bases: imines derived from anilines.[3] The term can be synonymous with azomethine which refers specifically to secondary aldimines (i.e. R−CH=NR' where R' ≠ H).[4]

  1. ^ IUPAC, Compendium of Chemical Terminology, 2nd ed. (the "Gold Book") (1997). Online corrected version: (2006–) "Schiff base". doi:10.1351/goldbook.S05498
  2. ^ Smith, Michael B.; March, Jerry (2007), Advanced Organic Chemistry: Reactions, Mechanisms, and Structure (6th ed.), New York: Wiley-Interscience, p. 1281, ISBN 978-0-471-72091-1
  3. ^ IUPAC, Compendium of Chemical Terminology, 2nd ed. (the "Gold Book") (1997). Online corrected version: (2006–) "anil". doi:10.1351/goldbook.A00357
  4. ^ IUPAC, Compendium of Chemical Terminology, 2nd ed. (the "Gold Book") (1997). Online corrected version: (2006–) "azomethines". doi:10.1351/goldbook.A00564
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