Squaramide

Squaramide is the organic compound with the formula O2C4(NH2)2.

Squaramides refer to a large class of derivatives wherein some of the H's are replaced by organic substituents.

Exploiting their rigid planar structures, these compounds are of interest as hydrogen-bond donors in supramolecular chemistry and squaramide catalysis.

[1] Squaramides exhibit 10-50x greater affinity for halides than do thioureas.

[2] Squaramides also find application in medicinal chemistry, metabolomics and material science due to their ability to selectively conjugate amines[3][4] Squaramide is prepared by ammonolysis of diesters of squaric acid:[5][6] N-Substituted squaramides are prepared similarly, using amines in place of ammonia.

Chloride-squaramide interaction in O 2 C 4 (NH(C 6 H 4 CF 3 ) 2 . The characteristic planarity of a squaramide is evident. [ 2 ]