Imide

Imide is a functional group in organic chemistry consisting of two acyl groups bound to nitrogen. These compounds are derived from carboxylic acids by replacement of the -OH group with -NH2.

Structure and properties

Imides are characterized by the formula (RC(O))2NR'. The most common imides are cyclic, derived from dicarboxylic acids where the nitrogen atom is part of the ring. In these compounds, the carbonyl centers are typically planar, and the functional groups are coplanar. The nitrogen atom is typically pyramidal.

Preparation

Imides are commonly synthesized by the condensation of a carboxylic acid with an amine. This reaction proceeds via the acyl chloride. The reaction of ammonia with phthalic anhydride illustrates this method:

C6H4(CO)2O + NH3 → C6H4(CO)2NH + H2O

Applications

Imides are used in a variety of applications in industry. They are used as curing agents in epoxy resins, as thermal stabilizers in polyvinyl chloride (PVC), and as crosslinking agents in polyurethane coatings. They are also used in the synthesis of pharmaceuticals and agrochemicals.

See also

• Acyl group
• Carboxylic acid
• Amide
• Anhydride
• Epoxy resin
• Polyvinyl chloride
• Polyurethane

References

Imide Resources
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