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Orthocarbonic acid
Hypothetical compound with formula C(OH)4 From Wikipedia, the free encyclopedia
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Orthocarbonic acid, carbon hydroxide, or methanetetrol is a chemical compound with the chemical formula H4CO4 or C(OH)4. Its molecular structure consists of a single carbon atom bonded to four hydroxyl groups. It would be therefore a fourfold alcohol. In theory it could lose four protons to give the hypothetical oxocarbon anion orthocarbonate CO4−4, and is therefore considered an oxoacid of carbon. Orthocarbonic acid is one of the group of ortho acids that have the general structure of RC(OH)3. The term ortho acid is also used to refer to the most hydroxylated acid in a set of oxoacids.
Orthocarbonic acid is highly unstable and long held to be a hypothetical chemical compound. Calculations show that it decomposes into carbonic acid and water:[2][3]
- H4CO4 → H2CO3 + H2O
However, orthocarbonic acid was first synthesized in 2025 from the electron-irradiation of a frozen mixture of water and carbon dioxide and identified by mass spectrometry.[4]
Researchers predict that orthocarbonic acid is stable at high pressure; hence it may form in the interior of the ice giant planets Uranus and Neptune, where water and methane are common.[5]
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Orthocarbonate anions
By loss of one through four protons, orthocarbonic acid could yield four anions: H3CO−4 (trihydrogen orthocarbonate), H2CO2−4 (dihydrogen orthocarbonate), HCO3−4 (hydrogen orthocarbonate), and CO4−4 (orthocarbonate).
Numerous salts of fully deprotonated CO4−4, such as Ca2CO4 (calcium orthocarbonate) or Sr2CO4 (strontium orthocarbonate), have been synthesized under high pressure conditions and structurally characterized by X-ray diffraction.[6][7][8][9] Strontium orthocarbonate, Sr2CO4, is stable at atmospheric pressure. Orthocarbonate is tetrahedral in shape, and is isoelectronic to orthonitrate. The C-O distance is 1.41 Å.[10] Sr3(CO4)O is an oxide orthocarbonate (tristrontium orthocarbonate oxide), also stable at atmospheric pressure.[11]
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Orthocarbonate esters
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The tetravalent moiety CO4 is found in stable organic compounds; they are formally esters of orthocarbonic acid, and therefore are called orthocarbonates. For example, tetraethoxymethane can be prepared by the reaction between chloropicrin and sodium ethoxide in ethanol.[12] Polyorthocarbonates are stable polymers that might have applications in absorbing organic solvents in waste treatment processes,[13] or in dental restorative materials.[14] The explosive trinitroethylorthocarbonate possesses an orthocarbonate core.
A linear polymer which can be described as a (spiro) orthocarbonate ester of pentaerythritol, whose formula could be written as [(−CH2)2C(CH2−)2 (−O)2C(O−)2]n, was synthesized in 2002.[15]
The carbon atom in the spiro ester bis-catechol orthocarbonate was found to have tetrahedral bond geometry, contrasting with the square planar geometry of the silicon atom in the analogous orthosilicate ester.[16]
Orthocarbonates may exist in several conformers, that differ by the relative rotation of the C–O–C bridges. The conformation structures of some esters, such as tetraphenoxymethane, tetrakis(3,5-dimethyl-phenoxy)methane, and tetrakis(4-bromophenoxy)methane have been determined by X-ray diffraction.[17]
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See also
- Pentaerythritol, C(CH2OH)4
- Silicic acid, Si(OH)4
- Carbonic acid, H2CO3
References
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