Tetrahydroxy-1,4-benzoquinone, also called tetrahydroxy-''p''-benzoquinone, tetrahydroxybenzoquinone, or tetrahydroxyquinone (THBQ, THQ), is an

organic compound Some chemical authorities define an organic compound as a chemical compound that contains a carbon–hydrogen or carbon–carbon bond; others consider an organic compound to be any chemical compound that contains carbon. For example, carbon-co ...

with formula . Its molecular structure consists of a

cyclohexadiene Cyclohexadiene may refer to: * Cyclohexa-1,3-diene, * Cyclohexa-1,4-diene, See also

* Benzene or its theoretical isomer ''1,3,5-Cyclohexatriene'' * Cyclohexene {{chemistry index ...

ring with four

hydroxyl In chemistry, a hydroxy or hydroxyl group is a functional group with the chemical formula and composed of one oxygen atom covalently bonded to one hydrogen atom. In organic chemistry, alcohols and carboxylic acids contain one or more hydroxy ...

groups and two

ketone In organic chemistry, a ketone is an organic compound with the structure , where R and R' can be a variety of carbon-containing substituents. Ketones contain a carbonyl group (a carbon-oxygen double bond C=O). The simplest ketone is acetone ( ...

groups in opposite ( ''para'') positions. The compound gives a light red solution in water, and crystallizes as the glistening bluish-black (but non-conducting)

dihydrate In chemistry, a hydrate is a substance that contains water or its constituent elements. The chemical state of the water varies widely between different classes of hydrates, some of which were so labeled before their chemical structure was understo ...

. The compound can be synthesized from

glyoxal Glyoxal is an organic compound with the chemical formula OCHCHO. It is the smallest dialdehyde (a compound with two aldehyde groups). It is a crystalline solid, white at low temperatures and yellow near the melting point (15 °C). The liquid ...

or from ''myo''-inositol, a natural compound widely present in plants. THBQ forms an

adduct In chemistry, an adduct (; alternatively, a contraction of "addition product") is a product of a direct addition of two or more distinct molecules, resulting in a single reaction product containing all atoms of all components. The resultant is ...

with 4,4′-bipyridine in a 2:3 ratio.

Salts of THBQ

Like most

phenol Phenol (also known as carbolic acid, phenolic acid, or benzenol) is an aromatic organic compound with the molecular formula . It is a white crystalline solid that is volatile and can catch fire. The molecule consists of a phenyl group () ...

s, THBQ is

acid An acid is a molecule or ion capable of either donating a proton (i.e. Hydron, hydrogen cation, H+), known as a Brønsted–Lowry acid–base theory, Brønsted–Lowry acid, or forming a covalent bond with an electron pair, known as a Lewis ...

ic and easily loses the four hydrogen ions from the

groups, yielding anions such as and . The

calcium Calcium is a chemical element; it has symbol Ca and atomic number 20. As an alkaline earth metal, calcium is a reactive metal that forms a dark oxide-nitride layer when exposed to air. Its physical and chemical properties are most similar to it ...

salt is the dark purple pigment produced from inositol by '' Chromohalobacter beijerinckii'' in the fermentation of salt

bean A bean is the seed of some plants in the legume family (Fabaceae) used as a vegetable for human consumption or animal feed. The seeds are often preserved through drying (a ''pulse''), but fresh beans are also sold. Dried beans are traditi ...

s, already noted by T. Hof in 1935. The dark purple and insoluble dipotassium salt was prepared by Preisler and

Berger Berger is a surname in both German language, German and French language, French, although there is no etymological connection between the names in the two languages. The French surname is an occupational name for a shepherd, from Old French ''bergi ...

in 1942, by oxidizing

inositol In biochemistry, medicine, and related sciences, inositol generally refers to ''myo''-inositol (formerly ''meso''-inositol), the most important stereoisomer of the chemical compound cyclohexane-1,2,3,4,5,6-hexol. Its elemental formula, formula is ...

with

nitric acid Nitric acid is an inorganic compound with the formula . It is a highly corrosive mineral acid. The compound is colorless, but samples tend to acquire a yellow cast over time due to decomposition into nitrogen oxide, oxides of nitrogen. Most com ...

and reacting the result with

potassium carbonate Potassium carbonate is the inorganic compound with the formula . It is a white salt, which is soluble in water and forms a strongly alkaline solution. It is deliquescent, often appearing as a damp or wet solid. Potassium carbonate is mainly used ...

in the presence of oxygen. Reaction of this salt with

hydrochloric acid Hydrochloric acid, also known as muriatic acid or spirits of salt, is an aqueous solution of hydrogen chloride (HCl). It is a colorless solution with a distinctive pungency, pungent smell. It is classified as a acid strength, strong acid. It is ...

produces THBQ in good yield. The black tetrapotassium salt was prepared by

West West is one of the four cardinal directions or points of the compass. It is the opposite direction from east and is the direction in which the Sun sets on the Earth. Etymology The word "west" is a Germanic word passed into some Romance langu ...

and Niu in 1962, by reacting THBQ with potassium methoxide in

methanol Methanol (also called methyl alcohol and wood spirit, amongst other names) is an organic chemical compound and the simplest aliphatic Alcohol (chemistry), alcohol, with the chemical formula (a methyl group linked to a hydroxyl group, often ab ...

. The salt is diamagnetic and the infrared spectrum suggests that the C–C and C–O distances are all equal, with the ring slightly distorted in the "chair" conformation. Partial oxidation of affords a green, strongly

paramagnetic Paramagnetism is a form of magnetism whereby some materials are weakly attracted by an externally applied magnetic field, and form internal, induced magnetic fields in the direction of the applied magnetic field. In contrast with this behavior, ...

solid, conjectured to be , and complete oxidation yields potassium rhodizonate . The greenish-black

sodium Sodium is a chemical element; it has Symbol (chemistry), symbol Na (from Neo-Latin ) and atomic number 11. It is a soft, silvery-white, highly reactive metal. Sodium is an alkali metal, being in group 1 element, group 1 of the peri ...

salt was described by Fatiadi and Sanger in 1962. The dark-violet

lithium Lithium (from , , ) is a chemical element; it has chemical symbol, symbol Li and atomic number 3. It is a soft, silvery-white alkali metal. Under standard temperature and pressure, standard conditions, it is the least dense metal and the ...

salt has been proposed as an electrode material for batteries as it can be oxidized to the rhodizonate and reduced to the hexahydroxybenzene salt . In the absence of oxygen, is stable to about 450 °C and then decomposes leaving a residue of

lithium carbonate Lithium carbonate is an inorganic compound, the lithium salt of carbonic acid with the chemical formula, formula . This white Salt (chemistry), salt is widely used in processing metal oxides. It is on the WHO Model List of Essential Medicines, Wor ...

. Indeed, the rhodizonate appears to disproportionate at about 400 °C into and

cyclohexanehexone Cyclohexanehexone, also known as hexaketocyclohexane and triquinoyl, is an organic compound with formula , the sixfold ketone of cyclohexane. It is an oxide of carbon (an oxocarbon), a hexamer of carbon monoxide. The compound is expected to be hi ...

that promptly decomposes into

carbon monoxide Carbon monoxide (chemical formula CO) is a poisonous, flammable gas that is colorless, odorless, tasteless, and slightly less dense than air. Carbon monoxide consists of one carbon atom and one oxygen atom connected by a triple bond. It is the si ...

carbon dioxide Carbon dioxide is a chemical compound with the chemical formula . It is made up of molecules that each have one carbon atom covalent bond, covalently double bonded to two oxygen atoms. It is found in a gas state at room temperature and at norma ...

, and carbon. forms a

hydrate In chemistry, a hydrate is a substance that contains water or its constituent elements. The chemical state of the water varies widely between different classes of hydrates, some of which were so labeled before their chemical structure was understo ...

that loses its water at about 250 °C.

References

{{reflist Organic acids 1,4-Benzoquinones Tetrols Hydroxybenzoquinones Polyphenols