In organic chemistry

Organic chemistry

Organic chemistry is a subdiscipline within chemistry involving the scientific study of the structure, properties, composition, reactions, and preparation of carbon-based compounds, hydrocarbons, and their derivatives...

, an aldimine is an imine

Imine

An imine is a functional group or chemical compound containing a carbon–nitrogen double bond, with the nitrogen attached to a hydrogen atom or an organic group. If this group is not a hydrogen atom, then the compound is known as a Schiff base...

 that is an analog of an aldehyde

Aldehyde

An aldehyde is an organic compound containing a formyl group. This functional group, with the structure R-CHO, consists of a carbonyl center bonded to hydrogen and an R group....

.
As such, aldimines have the general formula R–CH=N–R'. Aldimines are similar to ketimines, which are analogs of ketone

Ketone

In organic chemistry, a ketone is an organic compound with the structure RCR', where R and R' can be a variety of atoms and groups of atoms. It features a carbonyl group bonded to two other carbon atoms. Many ketones are known and many are of great importance in industry and in biology...

s.

An important subset of aldimines are the Schiff base

Schiff base

A Schiff base, named after Hugo Schiff, is a compound with a functional group that contains a carbon-nitrogen double bond with the nitrogen atom connected to an aryl or alkyl group, not hydrogen....

s,
in which the substituent on the nitrogen

Nitrogen

Nitrogen is a chemical element that has the symbol N, atomic number of 7 and atomic mass 14.00674 u. Elemental nitrogen is a colorless, odorless, tasteless, and mostly inert diatomic gas at standard conditions, constituting 78.08% by volume of Earth's atmosphere...

 atom (R') is an
alkyl or aryl group (i.e. not a
hydrogen

Hydrogen

Hydrogen is the chemical element with atomic number 1. It is represented by the symbol H. With an average atomic weight of , hydrogen is the lightest and most abundant chemical element, constituting roughly 75% of the Universe's chemical elemental mass. Stars in the main sequence are mainly...

 atom).

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:

1. by replacing the final -e of the parent hydride
   Parent hydride
   In IUPAC nomenclature, a parent hydride is an unbranched acyclic or cyclic structure to which only hydrogen atoms are attached. Parent hydrides are parent structures that contain one or more hydrogen atoms...
   
   , 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.