Squaric acid

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Structure of squaric acid: the molecule is not a perfect square, as the carbon–carbon bond lengths are not quite equal.
Structure of squaric acid: the molecule is not a perfect square, as the carbon–carbon bond lengths are not quite equal.

Squaric acid, also called quadratic acid, because its four carbon atoms form a square, is an acid with chemical formula C4H2O4 and CAS number 2892-51-5. It is one of the oxocarbonic acids.

It appears a white crystalline powder, and the melting point is 293 °C.

Medically, it can be used for the successful treatment of warts. It is also used treating alopecia areata or alopecia totalis/universalis (autoimmune hair loss) through topical immunotherapy involving the production of an allergic rash.

Squaric acid is also used to synthesize photosensitive squaraine dyes and inhibitors of protein tyrosine phosphatases.

The high acidity with pKa = 1.5 for the first proton and pKa = 3.4 for the second is attributable to resonance stabilization of the anion.[1] Because the negative charges are equally distributed between each oxygen atom, the dianion of squaric acid is completely symmetrical (unlike squaric acid itself) with all C-C and C-O bond lengths identical.

Squaric acid dianion resonance forms

The original synthesis started from reaction of 1-chloro-1,2,2-trifluoroethylene with zinc to perfluorocyclobutene. This compound was converted to 1,2-diethoxy-3,3,4,4-tetrafluoro-1-cyclobutene with ethanol. Hydrolysis gives the squaric acid. [2]

[edit] See also

[edit] References

  1. ^ New Aromatic Anions. III. Molecular Orbital Calculations on Oxygenated Anions Robert West, David L. Powell J. Am. Chem. Soc.; 1963; 85(17); 2577-2579.
  2. ^ Hydrolysis Reactions of Halogenated Cyclobutene Ethers: Synthesis of Diketocyclobutenediol J. D. Park, S. Cohen, and J. R. Lacher J. Am. Chem. Soc.; 1962; 84(15) pp 2919 - 2922. doi:10.1021/ja00874a015