Benzoquinonetetracarboxylic acid

Benzoquinonetetracarboxylic acid
Names
	Preferred IUPAC name 3,6-Dioxocyclohexa-1,4-diene-1,2,4,5-tetracarboxylic acid
Identifiers
CAS Number	500797-27-3 [GSRS];
3D model (JSmol)	Interactive image;
ChemSpider	310781 ;
PubChem CID	350050;
UNII	5BE47MRU9L;
CompTox Dashboard (EPA)	DTXSID101029309 ;
	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;
	SMILES C1(=C(C(=O)C(=C(C1=O)C(=O)O)C(=O)O)C(=O)O)C(=O)O;
Properties
Chemical formula	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). verify (what is ?) 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
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]

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 issue 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.

[hamm-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

[zapa-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.

[nef1887-3] J. U. Nef (1887), Annalen, volume 237, page 19. Cited by Zapadinskii et al.

[nef1890-4] J. U. Nef (1890), Annalen, volume 258, page 282. Cited by Zapadinskii et al.

[1]

[2]

[3]

[4]

See also

References