Benzoquinonetetracarboxylic acid

Benzoquinonetetracarboxylic acid

Names
IUPAC name 3,6-dioxocyclohexa-1,4-diene-1,2,4,5-tetracarboxylic acid
Identifiers
ChemSpider	310781
Jmol interactive 3D	Image
PubChem	350050
InChI InChI=1S/C10H4O10/c11-5-1(7(13)14)2(8(15)16)6(12)4(10(19)20)3(5)9(17)18/h(H,13,14)(H,15,16)(H,17,18)(H,19,20) Key: DMCTUEIMZPODLV-UHFFFAOYSA-N InChI=1/C10H4O10/c11-5-1(7(13)14)2(8(15)16)6(12)4(10(19)20)3(5)9(17)18/h(H,13,14)(H,15,16)(H,17,18)(H,19,20) Key: DMCTUEIMZPODLV-UHFFFAOYAE
SMILES C1(=C(C(=O)C(=C(C1=O)C(=O)O)C(=O)O)C(=O)O)C(=O)O
Properties
Chemical formula	C10H4O10
Molar mass	284.14 g/mol
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
verify (what is  ?)
Infobox references

In chemistry, 1,4-benzoquinonetetracarboxylic acid is an organic compound with formula C
10H
4O
10, or (C₆O₂)(-(CO)OH)₄, which can be viewed as deriving from para-benzoquinone C
6H
4O
2 through replacement of the four hydrogen atoms by carboxyl functional groups -(CO)OH.

By removal of four protons, the acid is expected to yield the anion C
10O4−
10, benzoquinonetetracarboxylate, which is one of the oxocarbon anions (consisting solely of oxygen and carbon. By loss of 1 through 3 protons it forms the anions C
10H
3O−
10, C
10H
2O2−
10, and C
10H
1O3−
10, called respectively trihydrogen-, dihydrogen-, and hydrogenbenzoquinonetetracarboxylate. The same names are used for the corresponding esters.

Removal of two water molecules gives the compound benzoquinonetetracarboxylic dianhydride, C
10O
8, one of the oxides of carbon.^[1]

The acid can be obtained by from durene (1,2,4,5-tetramethylbenzene) via dinitropyromellitic and diaminopyromellitic acids.^[2][3][4]

See also

• Mellitic acid C
  12H
  6O
  12
• Tetrahydroxybenzoquinone C
  6H
  4O
  6
• Benzenehexol C
  6H
  6O
  6

References

1. P. R. Hammond (1963), 1,4-Benzoquinone Tetracarboxylic Acid Dianhydride, C10O8: A Strong Acceptor. Science, Vol. 142. no. 3591, p. 502 doi:10.1126/science.142.3591.502
2. B. I. Zapadinskii, B. I. Liogon'kii, and A. A. Berlin (1973), Syntheses of Tetracarboxylic Acids. Russian Chemical Reviews, volume 42 issue 11, page 939. Online version accessed on 2010-01-03.
3. J. U. Nef (1887), Annalen, volume 237, page 19. Cited by Zapadinskii et al.
4. J. U. Nef (1890), Annalen, volume 258, page 282. Cited by Zapadinskii et al.