Benzoquinonetetracarboxylic acid

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.

Benzoquinone­tetracarboxylic acid
Names
Preferred IUPAC name
3,6-Dioxocyclohexa-1,4-diene-1,2,4,5-tetracarboxylic acid
Identifiers
3D model (JSmol)
ChemSpider
  • 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).
☒N verify (what is checkY☒N ?)
Infobox references

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.
This article is issued from Wikipedia. The text is licensed under Creative Commons - Attribution - Sharealike. Additional terms may apply for the media files.