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Concept
Imide
Summary
In organic chemistry, an imide is a functional group consisting of two acyl groups bound to nitrogen. The compounds are structurally related to acid anhydrides, although imides are more resistant to hydrolysis. In terms of commercial applications, imides are best known as components of high-strength polymers, called polyimides. Inorganic imides are also known as solid state or gaseous compounds, and the imido group (=NH) can also act as a ligand.
Most imides are cyclic compounds derived from dicarboxylic acids, and their names reflect the parent acid. Examples are succinimide, derived from succinic acid, and phthalimide, derived from phthalic acid. For imides derived from amines (as opposed to ammonia), the N-substituent is indicated by a prefix. For example, N-ethylsuccinimide is derived from succinic acid and ethylamine. Isoimides are isomeric with normal imides and have the formula RC(O)OC(NR′)R′′. They are often intermediates that convert to the more symmetrical imides. Organic compounds called carbodiimides have the formula RN=C=NR. They are unrelated to imides.
The PubChem links gives access to more information on the compounds, including other names, ids, toxicity and safety.
{| class="wikitable"
|+
!n!!Common name!!Systematic name!!Structure!!PubChem!!parent acid!!structure
|-
|2||Succinimide||Pyrrolidine-2,5-dione||||11439||Succinic acid||
|-
|2, unsaturated, cis carbon-carbon double bonds||Maleimide||Pyrrole-2,5-dione|| ||10935||Maleic acid||
|-
|3||Glutarimide||Piperidine-2,6-dione||||70726||Glutaric acid||
|-
|6||Phthalimide||Isoindole-1,3-dione||||6809||Phthalic acid||
|}
Being highly polar, imides exhibit good solubility in polar media. The N–H center for imides derived from ammonia is acidic and can participate in hydrogen bonding. Unlike the structurally related acid anhydrides, they resist hydrolysis and some can even be recrystallized from boiling water.
Many high strength or electrically conductive polymers contain imide subunits, i.e., the polyimides.
Official source
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