Chemistry:Orthocarbonic acid

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Short description: Hypothetical compound with formula C(OH)4
"Carbon hydroxide" redirects here. For the C(OH)
2 free radical, see Dihydroxymethylidene.
Orthocarbonic acid
Stereo skeletal formula of orthocarbonic acid
Stereo skeletal formula of orthocarbonic acid
Ball and stick model of orthocarbonic acid
Ball and stick model of orthocarbonic acid
Names
Preferred IUPAC name
Methanetetrol[1]
Systematic IUPAC name
Orthocarbonic acid
Other names
  • Carbon tetrahydroxide
Identifiers
3D model (JSmol)
ChemSpider
Properties
C(OH)
4
Molar mass 80.039 g·mol−1
Related compounds
Other cations
Related compounds
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Orthocarbonic acid (also known as methanetetrol) is a chemical compound with the chemical formula H
4CO
4 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 highly unstable and long held to be a hypothetical chemical compound. Calculations show that it decomposes into carbonic acid and water:[2][3]

H
4CO
4 → H
2CO
3 + H
2O

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; thus, it may form in the interior of the ice giant planets Uranus and Neptune, where water and methane are common.[5]

Orthocarbonate anions

By loss of one through four protons, orthocarbonic acid could yield four anions: H
3CO−
4 (trihydrogen orthocarbonate), H
2CO2−
4 (dihydrogen orthocarbonate), HCO3−
4 (hydrogen orthocarbonate), and CO4−
4 (orthocarbonate).

Numerous salts of fully deprotonated CO4−
4, such as Ca
2CO
4 (calcium orthocarbonate) or Sr
2CO
4 (strontium orthocarbonate), have been synthesized under high pressure conditions and structurally characterized by X-ray diffraction.[6][7][8][9] Strontium orthocarbonate, Sr
2CO
4, is stable at atmospheric pressure. Orthocarbonate is tetrahedral in shape, and is isoelectronic to orthonitrate. The C-O distance is 1.41 Å.[10] Sr
3(CO
4)O is an oxide orthocarbonate (tristrontium orthocarbonate oxide), also stable at atmospheric pressure.[11]

Orthocarbonate esters

The tetravalent moiety CO
4 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 [(–CH
2)
2C(CH
2–)
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]

See also

References

  1. ↑ "Methanetetrol - PubChem Public Chemical Database". The PubChem Project. USA: National Center for Biotechnology Information. https://pubchem.ncbi.nlm.nih.gov/compound/9547954. 
  2. ↑ Bohm S.; Antipova D.; Kuthan J. (1997). "A Study of Methanetetraol Dehydration to Carbonic Acid". International Journal of Quantum Chemistry 62 (3): 315–322. doi:10.1002/(SICI)1097-461X(1997)62:3<315::AID-QUA10>3.0.CO;2-8. 
  3. ↑ Carboxylic Acids and Derivatives "Carboxylic Acids and Derivatives". Glossary of Class Names of Organic Compounds and Reactive Intermediaries Based on Structure (IUPAC Recommendations 1994). 1994. http://www.chem.qmul.ac.uk/iupac/class/carba.html#15. 
  4. ↑ Marks, Joshua H.; Bai, Xilin; Nikolayev, Anatoliy A.; Gong, Qi'ang; McAnally, Mason; Wang, Jia; Pan, Yang; Fortenberry, Ryan C. et al. (14 July 2025). "Methanetetrol and the final frontier in ortho acids". Nature Communications. doi:10.1038/s41467-025-61561-z. 
  5. ↑ G. Saleh; A. R. Oganov (2016). "Novel Stable Compounds in the C-H-O Ternary System at High Pressure". Scientific Reports 6. doi:10.1038/srep32486. PMID 27580525. Bibcode: 2016NatSR...632486S. 
  6. ↑ Sagatova, Dinara; Shatskiy, Anton; Sagatov, Nursultan; Gavryushkin, Pavel N.; Litasov, Konstantin D. (2020). "Calcium orthocarbonate, Ca2CO4-Pnma: A potential host for subducting carbon in the transition zone and lower mantle". Lithos 370-371. doi:10.1016/j.lithos.2020.105637. ISSN 0024-4937. Bibcode: 2020Litho.37005637S. 
  7. ↑ Binck, Jannes; Laniel, Dominique; Bayarjargal, Lkhamsuren; Khandarkhaeva, Saiana; Fedotenko, Timofey; Aslandukov, Andrey; Milman, Victor; Glazyrin, Konstantin et al. (2022). "Synthesis of calcium orthocarbonate, Ca2CO4-Pnma at P-T conditions of Earth's transition zone and lower mantle". American Mineralogist 107 (3): 336–342. doi:10.2138/am-2021-7872. Bibcode: 2022AmMin.107..336B. https://bib-pubdb1.desy.de/search?p=id:%22PUBDB-2022-02872%22. 
  8. ↑ Laniel, Dominique; Binck, Jannes; Winkler, Björn; Vogel, Sebastian; Fedotenko, Timofey; Chariton, Stella; Prakapenka, Vitali; Milman, Victor et al. (2021). "Synthesis, crystal structure and structure–property relations of strontium orthocarbonate, Sr2CO4". Acta Crystallographica Section B 77 (1): 131–137. doi:10.1107/S2052520620016650. ISSN 2052-5206. Bibcode: 2021AcCrB..77..131L. 
  9. ↑ Gavryushkin, Pavel N.; Sagatova, Dinara N.; Sagatov, Nursultan; Litasov, Konstantin D. (2021). "Formation of Mg-Orthocarbonate through the Reaction MgCO3 + MgO = Mg2CO4 at Earth's Lower Mantle P–T Conditions". Crystal Growth & Design 21 (5): 2986–2992. doi:10.1021/acs.cgd.1c00140. 
  10. ↑ Spahr, Dominik; Binck, Jannes; Bayarjargal, Lkhamsuren; Luchitskaia, Rita; Morgenroth, Wolfgang; Comboni, Davide; Milman, Victor; Winkler, Björn (4 April 2021). "Tetrahedrally Coordinated sp3-Hybridized Carbon in Sr2CO4 Orthocarbonate at Ambient Conditions". Inorganic Chemistry 60 (8): 5419–5422. doi:10.1021/acs.inorgchem.1c00159. PMID 33813824. 
  11. ↑ Spahr, Dominik; König, Jannes; Bayarjargal, Lkhamsuren; Gavryushkin, Pavel N.; Milman, Victor; Liermann, Hanns-Peter; Winkler, Björn (4 October 2021). "Sr 3 [CO 4 ]O Antiperovskite with Tetrahedrally Coordinated sp 3 -Hybridized Carbon and OSr 6 Octahedra". Inorganic Chemistry 60 (19): 14504–14508. doi:10.1021/acs.inorgchem.1c01900. PMID 34520201. 
  12. ↑ Orthocarbonic acid, tetraethyl ester Organic Syntheses, Coll. Vol. 4, p. 457 (1963); Vol. 32, p. 68 (1952).
  13. ↑ Sonmez, H.B.; Wudl, F. (2005). "Cross-linked poly(orthocarbonate)s as organic solvent sorbents". Macromolecules 38 (5): 1623–1626. doi:10.1021/ma048731x. Bibcode: 2005MaMol..38.1623S. 
  14. ↑ Stansbury, J.W. (1992). "Synthesis and evaluation of new oxaspiro monomers for double ring-opening polymerization". Journal of Dental Research 71 (7): 1408–1412. doi:10.1177/00220345920710070901. PMID 1629456. http://jdr.iadrjournals.org/cgi/content/abstract/71/7/1408. Retrieved 2008-06-19. 
  15. ↑ David T. Vodak, Matthew Braun, Lykourgos Iordanidis, Jacques Plévert, Michael Stevens, Larry Beck, John C. H. Spence, Michael O'Keeffe, Omar M. Yaghi (2002): "One-Step Synthesis and Structure of an Oligo(spiro-orthocarbonate)". Journal of the American Chemical Society, volume 124, issue 18, pages 4942–4943. doi:10.1021/ja017683i
  16. ↑ H. Meyer, G. Nagorsen (1979): "Structure and reactivity of the orthocarbonic and orthosilicic acid esters of pyrocatechol". Angewandte Chemie International Edition in English, volume 18, issue 7, pages 551-553. doi:10.1002/anie.197905511
  17. ↑ N. Narasimhamurthy, H. Manohar, Ashoka G. Samuelson, Jayaraman Chandrasekhar (1990): "Cumulative anomeric effect: A theoretical and x-ray diffraction study of orthocarbonates". Journal of the American Chemical Society, volume 112, issue 8, pages 2937–2941. doi:10.1021/ja00164a015



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