Orthocarbonic acid (methanetetrol) is the name given to a

hypothetical compound A hypothetical chemical compound is a chemical compound that has been conceived of, but is not known to have been synthesized, observed, or isolated (identified or shown to exist). Some hypothetical compounds cannot form at all. Others might tur ...

with the

chemical formula In chemistry, a chemical formula is a way of presenting information about the chemical proportions of atoms that constitute a particular chemical compound or molecule, using chemical element symbols, numbers, and sometimes also other symbols, ...

or . Its molecular structure consists of a single

carbon atom Carbon () is a chemical element with the chemical symbol, symbol C and atomic number 6. It is nonmetallic and tetravalence, tetravalent—its atom making four electrons available to form covalent bond, covalent chemical bonds. It belongs to gro ...

bonded to four hydroxy groups. It would be therefore a fourfold

alcohol Alcohol most commonly refers to: * Alcohol (chemistry), an organic compound in which a hydroxyl group is bound to a carbon atom * Alcohol (drug), an intoxicant found in alcoholic drinks Alcohol may also refer to: Chemicals * Ethanol, one of sev ...

. In theory it could lose four

protons A proton is a stable subatomic particle, symbol , H+, or 1H+ with a positive electric charge of +1 ''e'' elementary charge. Its mass is slightly less than that of a neutron and 1,836 times the mass of an electron (the proton–electron mass ...

to give the hypothetical

oxocarbon anion In chemistry, an oxocarbon anion is a negative ion consisting solely of carbon and oxygen atoms, and therefore having the general formula for some integers ''x'', ''y'', and ''n''. The most common oxocarbon anions are carbonate, , and oxalate, ...

(orthocarbonate), and is therefore considered an

oxoacid An oxyacid, oxoacid, or ternary acid is an acid that contains oxygen. Specifically, it is a compound that contains hydrogen, oxygen, and at least one other element, with at least one hydrogen atom bonded to oxygen that can dissociate to produce ...

of carbon. The compound has also been given the nickname of "

Hitler Adolf Hitler (; 20 April 188930 April 1945) was an Austrian-born German politician who was dictator of Germany from 1933 until his death in 1945. He rose to power as the leader of the Nazi Party, becoming the chancellor in 1933 and then ...

's Acid" due to the

Ball-and-stick model In chemistry, the ball-and-stick model is a molecular model of a chemical substance which displays both the three-dimensional position of the atoms and the bonds between them. The atoms are typically represented by spheres, connected by rods w ...

of the compound resembling the

Swastika The swastika (卐 or 卍) is an ancient religious and cultural symbol, predominantly in various Eurasian, as well as some African and American cultures, now also widely recognized for its appropriation by the Nazi Party and by neo-Nazis. It ...

symbol. Orthocarbonic acid is highly unstable. Calculations show that it decomposes spontaneously into carbonic acid and water: : H4CO4 -> H2CO3 + H2O Orthocarbonic acid is one of the group of ''

ortho acid In organic chemistry, ortho acids are organic, hypothetical compounds having the structure (R = alkyl or aryl). Ortho acids themselves are unstable and cannot be isolated. However, orthoesters can be synthesized by the Pinner reaction, in which ...

s'' that have the general structure of .The term ''ortho acid'' is also used to refer to the most hydroxylated acid in a set of

s. Researchers predict that orthocarbonic acid is stable at high pressure; hence it may form in the interior of the

ice giant An ice giant is a giant planet composed mainly of elements heavier than hydrogen and helium, such as oxygen, carbon, nitrogen, and sulfur. There are two ice giants in the Solar System: Uranus and Neptune. In astrophysics and planetary science t ...

planets

Uranus Uranus is the seventh planet from the Sun. Its name is a reference to the Greek god of the sky, Uranus (mythology), Uranus (Caelus), who, according to Greek mythology, was the great-grandfather of Ares (Mars (mythology), Mars), grandfather ...

and

Neptune Neptune is the eighth planet from the Sun and the farthest known planet in the Solar System. It is the fourth-largest planet in the Solar System by diameter, the third-most-massive planet, and the densest giant planet. It is 17 times ...

, where water and

methane Methane ( , ) is a chemical compound with the chemical formula (one carbon atom bonded to four hydrogen atoms). It is a group-14 hydride, the simplest alkane, and the main constituent of natural gas. The relative abundance of methane on Eart ...

are common.

Orthocarbonate anions

By loss of one through four protons, orthocarbonic acid could yield four anions: , , , and . Numerous

salts In chemistry, a salt is a chemical compound consisting of an ionic assembly of positively charged cations and negatively charged anions, which results in a compound with no net electric charge. A common example is table salt, with positively cha ...

of fully deprotonated , such as or , have been synthesized under high pressure conditions and structurally characterized by X-ray diffraction. Strontium orthocarbonate, , is stable at atmospheric pressure. Orthocarbonate is

tetrahedral In geometry, a tetrahedron (plural: tetrahedra or tetrahedrons), also known as a triangular pyramid, is a polyhedron composed of four triangular faces, six straight edges, and four vertex corners. The tetrahedron is the simplest of all the o ...

in shape. The C-O distance is 1.41 Å. is an oxide orthocarbonate, also stable at

atmospheric pressure Atmospheric pressure, also known as barometric pressure (after the barometer), is the pressure within the atmosphere of Earth. The standard atmosphere (symbol: atm) is a unit of pressure defined as , which is equivalent to 1013.25 millibars, 7 ...

Orthocarbonate esters

The

tetravalent In chemistry, the valence (US spelling) or valency (British spelling) of an element is the measure of its combining capacity with other atoms when it forms chemical compounds or molecules. Description The combining capacity, or affinity of an ...

moiety Moiety may refer to: Chemistry * Moiety (chemistry), a part or functional group of a molecule ** Moiety conservation, conservation of a subgroup in a chemical species Anthropology * Moiety (kinship), either of two groups into which a society is ...

CO₄ is found in stable organic compounds; they are formally

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 ar ...

s of orthocarbonic acid, and therefore are called orthocarbonates. For example, tetraethoxymethane can be prepared by the reaction between

chloropicrin Chloropicrin, also known as PS and nitrochloroform, is a chemical compound currently used as a broad-spectrum antimicrobial, fungicide, herbicide, insecticide, and nematicide. It was used as a poison gas in World War I. Its chemical structural for ...

and

sodium ethoxide Sodium ethoxide, also referred to as sodium ethylate, is the ionic, organic compound with the formula , or NaOEt (Et = ethane). It is a white solid, although impure samples appear yellow or brown. It dissolves in polar solvents such as ethanol. ...

in ethanol.Orthocarbonic acid, tetraethyl ester
''Organic Syntheses'', Coll. Vol. 4, p. 457 (1963); Vol. 32, p. 68 (1952). Polyorthocarbonates are stable

polymer A polymer (; Greek '' poly-'', "many" + ''-mer'', "part") is a substance or material consisting of very large molecules called macromolecules, composed of many repeating subunits. Due to their broad spectrum of properties, both synthetic a ...

s that might have applications in absorbing organic solvents in waste treatment processes, or in dental restorative materials. The explosive

trinitroethylorthocarbonate Trinitroethylorthocarbonate also known as TNEOC is an oxidizer with excellent chemical stability. Its explosion point is 238 °C, and it begins to be decomposed at 200 °C. Its explosion heat is 5.797 J/g and specific volume is 694 L/kg ...

possesses an orthocarbonate core.

References

{{DEFAULTSORT:Orthocarbonic Acid Hypothetical chemical compounds Oxoacids Tetrols Hydroxides

Orthocarbonate anions

Orthocarbonate esters

See also

References