Squaramide is the organic compound with the formula O2C4(NH2)2. Not an amide in the usual sense, it is a derivative of squaric acid wherein the two OH groups are replaced by NH2 groups. 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 organocatalysis.[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]
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IUPAC name
3,4-diaminocyclobut-3-ene-1,2-dione
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3D model (JSmol)
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PubChem CID
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CompTox Dashboard (EPA)
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Properties | |
C4H4N2O2 | |
Molar mass | 112.088 g·mol−1 |
Appearance | white solid |
Melting point | 338–340 °C (640–644 °F; 611–613 K) |
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
Infobox references
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Squaramide is prepared by ammonolysis of diesters of squaric acid:[5][6]
N-Substituted squaramides are prepared similarly, using amines in place of ammonia.