Aldimine

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In organic chemistry, an aldimine is an imine which is derived from an aldehyde.[1] As such, aldimines have the general formula R–CH=N–R'.

An important subset of aldimines are the Schiff bases, in which the substituent on the nitrogen atom (R') is an alkyl or aryl group (i.e. not a hydrogen atom).[2]

[edit] Nomenclature

Nomenclature CH3–CH2–CH2–CH=NH CH3–CH=N–CH3
1 butanimine N-methylethanimine
2 butylideneazane ethylidene(methyl)azane
3 butylideneamine N-methylethylideneamine
obsolete butyraldehyde imine acetaldehyde N-methylimine

Aldimines may be named in three different manners:[3]

  1. by replacing the final -e of the parent hydride, R–CH3, with the suffix "-imine";
  2. as alkylidene derivatives of azane;
  3. (rare) as alkylidene derivatives of "amine".

An obsolete nomenclature treats aldimines as derivatives of a parent aldehyde.

[edit] References

  1. ^ International Union of Pure and Applied Chemistry (1995). "aldimines". Compendium of Chemical Terminology Internet edition.
  2. ^ International Union of Pure and Applied Chemistry (1995). "Schiff bases (Schiff's bases)". Compendium of Chemical Terminology Internet edition.
  3. ^ International Union of Pure and Applied Chemistry (1993). "Recommendation R-5.4.3." A Guide to IUPAC Nomenclature of Organic Compounds. Oxford: Blackwell Science. ISBN 0-632-03488-2. pp. 89–90.
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