Benzoquinonetetracarboxylic acid

Benzoquinonetetracarboxylic acid
IUPAC name 3,6-dioxocyclohexa-1,4-diene-1,2,4,5-tetracarboxylic acid
Identifiers
	PubChem	350050
ChemSpider	310781
Jmol-3D images	Image 1
SMILES C1(=C(C(=O)C(=C(C1=O)C(=O)O)C(=O)O)C(=O)O)C(=O)O
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
Properties
Molecular formula	C10H4O10
Molar mass	284.14 g/mol
Y (verify) (what is: Y/N?) Except where noted otherwise, data are given for materials in their standard state (at 25 °C (77 °F), 100 kPa)
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 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