Carbodiimides

General formula of the carbodiimides with the double-bonded carbodiimide residue marked blue . The radicals R ¹ and R ² are organyl radicals (alkyl radicals, aryl radicals, etc.) which can be the same (R ¹ = R ² ) or different (R ¹ ≠ R ² ).

In chemistry, carbodiimides are a group of organic compounds.

The parent compound carbodiimide (HN = C = NH) is unstable under normal conditions; it is in tautomeric equilibrium with cyanamide . Other carbodiimides do not occur naturally either, since they react spontaneously with water to form urea .

The best-known representatives of the carbodiimides are the substances dicyclohexylcarbodiimide (DCC), diisopropylcarbodiimide (DIC) and 1-ethyl-3- (3-dimethylaminopropyl) carbodiimide (EDC) used as reagents for dehydration in syntheses .

Manufacturing

Carbodiimides can be synthesized from N , N ′ -disubstituted ureas by splitting off water with the help of triphenylphosphine and carbon tetrachloride .

The first carbodiimides were synthesized by Hinterberger and Sinin in 1852 . Later, Nobel Prize winner John C. Sheehan used water-soluble carbodiimides in the synthesis of penicillin .

Individual evidence

1. ^ ^{A b} Henri Ulrich: Chemistry and technology of carbodiimides . John Wiley & Sons, 2007, ISBN 978-0-470-06510-5 ( page 1 in Google Book Search).
2. ↑ ^{a b c} Entry on carbodiimides. In: Römpp Online . Georg Thieme Verlag, accessed on April 19, 2014.