Benzoquinonetetracarboxylic acid
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| Names | |
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| IUPAC name
3,6-dioxocyclohexa-1,4-diene-1,2,4,5-tetracarboxylic acid
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| Identifiers | |
3D model (JSmol)
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PubChem CID
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CompTox Dashboard (EPA)
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| 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
10H
1O3−
10, called respectivey 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
- ^ 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
- ^ B. I. Zapadinskii, B. I. Liogon'kii, and A. A. Berlin (1973), Syntheses of Tetracarboxylic Acids. Russian Chemical Reviews, volume 42 isue 11, page 939. Online version accessed on 2010-01-03.
- ^ J. U. Nef (1887), Annalen, volume 237, page 19. Cited by Zapadinskii et al.
- ^ J. U. Nef (1890), Annalen, volume 258, page 282. Cited by Zapadinskii et al.