Imine

"Ketimine" redirects here. For the drug with a similar-sounding name, see ketamine.

File:Methanimine-2D.png

Methanimine is the simplest imine compound. This structural formula shows atoms as letters and chemical bonds as lines.

In organic chemistry, an imine is a chemical compound that has a carbon atom with a double bond to a nitrogen atom. The C=N functional group is called imino.

Types

Imines are divided into primary and secondary imines based on what else is connected to the nitrogen atom. If nitrogen is connected to hydrogen, it is a primary imine. If it is connected to carbon, it is a secondary imine.

Imines are also divided into groups depending on what the carbon is connected to. If it is connected to two other carbons, it is a ketimine (like a ketone). If it is connected to hydrogen, it is an aldimine (like an aldehyde).

Production

File:N-Ethylidenecyclohexylamine.svg

Cyclohexylamine and acetaldehyde react to make an imine. Sodium sulfate is a desiccant used to remove the water byproduct.

Imines are made by a condensation reaction between carbonyl compounds and ammonia or primary amines. Different types of ingredient give different types of imine: ketones give ketimines, aldehydes give aldimines, ammonia gives primary imines, and primary amines give secondary imines. This reaction makes water as a byproduct.

This condensation is reversible: an imine and a water molecule can react, breaking the imine apart into the original ingredients. (Breaking a molecule up with water is called hydrolysis.) Something needs to remove the water in order to keep the reaction going. This can be a process like distillation, or an added desiccant.

Imine Media

• Imine general structure B.svg

  The general structure of an imine

• Imine-synthesis.svg

  Imine synthesis from a primary amine and a carbonyl compound.

• Hexafluoroacetone imine.svg

  Hexafluoroacetone imine is an unusual primary ketimine that is readily isolable.

• Mannich.png

  Mannich reaction

• ImineReduction.svg

  Imine reduction

• PLP mechanism.svg

  Steps in pyridoxal phosphate-mediated reactions of alanine and cysteine, illustrating one biological role for aldimines.

• Aldimine-(primary)-skeletal.svg

  Primary aldimine, E-isomer

• Aldimine-(secondary)-skeletal.svg

  Secondary aldimine, E-isomer

• Imine-(primary)-skeletal.svg

  Strucure of a primary ketimine.

• Imine-(secondary)-skeletal.svg

  Strucure of a secondary ketimine.