Tetrahydroxy-1,4-benzoquinone bisoxalate
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Tetrahydroxy-1,4-benzoquinone bisoxalate is a
chemical compound A chemical compound is a chemical substance composed of many identical molecules (or molecular entities) containing atoms from more than one chemical element held together by chemical bonds. A molecule consisting of atoms of only one element ...
, an oxide of carbon with formula . Its molecule consists of a
1,4-benzoquinone 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 ...
core with the four
hydrogen Hydrogen is the chemical element with the symbol H and atomic number 1. Hydrogen is the lightest element. At standard conditions hydrogen is a gas of diatomic molecules having the formula . It is colorless, odorless, tasteless, non-to ...
atoms replaced by two
oxalate Oxalate (IUPAC: ethanedioate) is an anion with the formula C2O42−. This dianion is colorless. It occurs naturally, including in some foods. It forms a variety of salts, for example sodium oxalate (Na2C2O4), and several esters such as dimethyl ...
groups A group is a number of persons or things that are located, gathered, or classed together. Groups of people * Cultural group, a group whose members share the same cultural identity * Ethnic group, a group whose members share the same ethnic ide ...
. It can be seen as a fourfold
ester In chemistry, an ester is a compound derived from an oxoacid (organic or inorganic) in which at least one hydroxyl group () is replaced by an alkoxy group (), as in the substitution reaction of a carboxylic acid and an alcohol. Glycerides ...
of
tetrahydroxy-1,4-benzoquinone Tetrahydroxy-1,4-benzoquinone, also called tetrahydroxy-''p''-benzoquinone, tetrahydroxybenzoquinone, or tetrahydroxyquinone (THBQ, THQ), is an organic compound with formula . Its molecular structure consists of a cyclohexadiene ring with four h ...
and
oxalic acid Oxalic acid is an organic acid with the systematic name ethanedioic acid and formula . It is the simplest dicarboxylic acid. It is a white crystalline solid that forms a colorless solution in water. Its name comes from the fact that early invest ...
. The compound was first described by H. S. Verter, H. Porter, and R. Dominic in 1968. It was obtained by reacting tetrahydroxy-1,4-benzoquinone with
oxalyl chloride Oxalyl chloride is an organic chemical compound with the formula (COCl)2. This colorless, sharp-smelling liquid, the diacyl chloride of oxalic acid, is a useful reagent in organic synthesis. Preparation Oxalyl chloride was first prepared in 1892 ...
in
tetrahydrofuran Tetrahydrofuran (THF), or oxolane, is an organic compound with the formula (CH2)4O. The compound is classified as heterocyclic compound, specifically a cyclic ether. It is a colorless, water- miscible organic liquid with low viscosity. It is ...
. It is a yellow solid that can be crystallized as a tetrahydrofuran
solvate Solvation (or dissolution) describes the interaction of a solvent with dissolved molecules. Both ionized and uncharged molecules interact strongly with a solvent, and the strength and nature of this interaction influence many properties of the ...
, but could not be prepared in pure form. H. S. Verter, H. Porter, and R. Dominic (Verter, Porter and Dominic, 1968), ''A new carbon oxide: synthesis of tetrahydroxybenzoquinone bisoxalate''. Chemical Communications, p. 973b–974.


See also

* Tetrahydroxy-1,4-benzoquinone biscarbonate * Hexahydroxybenzene trisoxalate * Hexahydroxybenzene triscarbonate


References

{{Oxides of carbon Oxocarbons 1,4-Benzoquinones Oxalate esters Oxygen heterocycles Heterocyclic compounds with 3 rings