Benzoquinonetetracarboxylic acid

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Benzoquinone­tetracarboxylic acid
Benzoquinonetetracarboxylic acid.svg
Names
Preferred IUPAC name
3,6-Dioxocyclohexa-1,4-diene-1,2,4,5-tetracarboxylic acid
Identifiers
3D model (JSmol)
ChemSpider
PubChem CID
  • 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) X mark.svgN
    Key: DMCTUEIMZPODLV-UHFFFAOYSA-N X mark.svgN
  • 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
10
H
4
O
10
, or (C6O2)(-(CO)OH)4, which can be viewed as deriving from para-benzoquinone C
6
H
4
O
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
10
O4−
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
10
H
3
O
10
, C
10
H
2
O2−
10
, and C
10
HO3−
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
10
O
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

Related Research Articles

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1,4-Benzoquinone, commonly known as para-quinone, is a chemical compound with the formula C6H4O2. In a pure state, it forms bright-yellow crystals with a characteristic irritating odor, resembling that of chlorine, bleach, and hot plastic or formaldehyde. This six-membered ring compound is the oxidized derivative of 1,4-hydroquinone. The molecule is multifunctional: it exhibits properties of a ketone, being able to form oximes; an oxidant, forming the dihydroxy derivative; and an alkene, undergoing addition reactions, especially those typical for α,β-unsaturated ketones. 1,4-Benzoquinone is sensitive toward both strong mineral acids and alkali, which cause condensation and decomposition of the compound.

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Tetrahydroxy-1,4-benzoquinone, also called tetrahydroxy-p-benzoquinone, tetrahydroxybenzoquinone, or tetrahydroxyquinone, is an organic compound with formula C6O2(OH)4. Its molecular structure consists of a cyclohexadiene ring with four hydroxyl groups and two ketone groups in opposite (para) positions.

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<span class="mw-page-title-main">Ethylenetetracarboxylic acid</span> Chemical compound

Ethylenetetracarboxylic acid is an organic compound with formula C
6
H
4
O
8
, or (HO(OC)-)2C=C(-(CO)OH)2.

2,5-Dihydroxy-1,4-benzoquinone or 2,5-dihydroxy-para-benzoquinone is an organic compound with formula C
6
H
4
O
4
, formally derived from 1,4-benzoquinone by replacing two hydrogen atoms with hydroxyl (OH) groups. It is one of seven dihydroxybenzoquinone isomers. It is a yellow solid with planar molecules that exhibits ferroelectric properties.

<span class="mw-page-title-main">Furantetracarboxylic acid</span> Chemical compound

In chemistry, furantetracarboxylic acid is an organic compound with formula C
8
H
4
O
9
, or (C4O)(-(CO)OH)4, which can be viewed as deriving from furan C
4
H
4
O
through replacement of the four hydrogen atoms by carboxyl functional groups -(CO)OH.

<span class="mw-page-title-main">Benzoquinonetetracarboxylic dianhydride</span> Chemical compound

Benzoquinonetetracarboxylic dianhydride is an organic compound with formula C
10
O
8
which can be seen as the result of removing two molecules of water H
2
O
from benzoquinonetetracarboxylic acid.

<span class="mw-page-title-main">Hydromelonic acid</span> Chemical compound

Hydromelonic acid, is an elusive chemical compound with formula C
9
H
3
N
13
or (HNCN)
3
(C
6
N
7
)
, whose molecule would consist of a heptazine H3(C
6
N
7
)
molecule, with three cyanamido groups H–N=C=N– or N≡C–NH– substituted for the hydrogen atoms.

<span class="mw-page-title-main">Trioxoglutaric acid</span> Chemical compound

Trioxoglutaric acid or trioxopentanedioic acid is a hypothetical chemical compound with formula C5H2O7 or HO−(C=O)5−OH. It can be seen as a derivative of glutaric acid, hence its common name. It would be the next member of the series of fully oxidized straight-chain dicarboxylic acids, that starts with the oxalic, oxomalonic, and dioxosuccinic acids.

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.