Allophanic acid

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Allophanic acid
File:Allophanic acid.svg
Names
Preferred IUPAC name
Carbamoylcarbamic acid
Identifiers
3D model (JSmol)
1756623
ChEBI
ChemSpider
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KEGG
UNII
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  • InChI=1S/C2H4N2O3/c3-1(5)4-2(6)7/h(H,6,7)(H3,3,4,5)
    Key: AVWRKZWQTYIKIY-UHFFFAOYSA-N
  • C(=O)(N)NC(=O)O
Properties
C2H4N2O3
Molar mass 104.065 g·mol−1
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).

Allophanic acid is the organic compound with the formula H2NC(O)NHCO2H. It is a carbamic acid, the carboxylated derivative of urea. Biuret can be viewed as the amide of allophanic acid.

Treating urea with sodium bicarbonate is claimed to give allophanic acid:[1]

H2NC(O)NH2 + NaHCO3 → H2NC(O)NHCO2H + NaOH

Although allophanic acid per se may not have been purified, its conjugate base, H2NC(O)NHCO2, allophanate is well known. Salts of this anion have been characterized by X-ray crystallography.[2][3] The allophanate anion is the substrate for the enzyme allophanate hydrolase.

Allophanate esters arise from the condensation of carbamates.

File:Allophanat-Bildung.png

References

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