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Benzoquinonetetracarboxylic acid

Benzoquinone­tetracarboxylic acid
Names
Preferred IUPAC name
3,6-Dioxocyclohexa-1,4-diene-1,2,4,5-tetracarboxylic acid
Identifiers
3D model (JSmol)
ChemSpider
UNII
  • 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) ☒N
    Key: DMCTUEIMZPODLV-UHFFFAOYSA-N ☒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
  • C1(=C(C(=O)C(=C(C1=O)C(=O)O)C(=O)O)C(=O)O)C(=O)O
Properties
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).
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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
10HO3−
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

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.
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