Allophanic acid explained

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. The compound can be prepared by treating urea with sodium bicarbonate:[1]

H2NC(O)NH2 + NaHCO3 → H2NC(O)NHCO2H + NaOHThe anionicconjugate base, H2NC(O)NHCO2−, is called allophanate. 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.

References

  1. Reaction of urea with alkali metal carbonates. Karachinskii, S. V. . Dragalov, V. V. . Chimishkyan, A. L. . Tsvetkov, V. Yu.. Zhurnal Organicheskoi Khimii. 1987. 23. 93–6.  
  2. 10.1021/ja00153a022. Novel Hydrogen-Bonded Host Lattices Built of Urea and the Elusive Allophanate Ion. 1995. Mak. Thomas C. W.. Yip. Wai Hing. Li. Qi. Journal of the American Chemical Society. 117. 48. 11995–11996.
  3. 10.1080/10610279608233970. A Novel Inclusion Compound Consolidated by Host-host and Host-guest Hydrogen Bonding: (2-hydro-xyethyl)trimethylammonium Ions Included in a Channel Host Lattice Built of Urea Molecules and Allophanate Ions. 1996. Li. Qi. Mak. Thomas C. W.. Supramolecular Chemistry. 8. 73–80.

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