Orthocarbonic acid explained

Orthocarbonic acid, carbon hydroxide, methanetetrol is the name given to a hypothetical compound with the chemical formula or . 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, and is therefore considered an oxoacid of carbon.

Orthocarbonic acid is highly unstable. Calculations show that it decomposes into carbonic acid and water:[1] [2]

Orthocarbonic acid is one of the group of ortho acids that have the general structure of . The term ortho acid is also used to refer to the most hydroxylated acid in a set of oxoacids.

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.[3]

Orthocarbonate anions

By loss of one through four protons, orthocarbonic acid could yield four anions: (trihydrogen orthocarbonate), (dihydrogen orthocarbonate), (hydrogen orthocarbonate), and (orthocarbonate).

Numerous salts of fully deprotonated, such as (calcium orthocarbonate) or (strontium orthocarbonate), have been synthesized under high pressure conditions and structurally characterized by X-ray diffraction.[4] [5] [6] Strontium orthocarbonate,, is stable at atmospheric pressure. Orthocarbonate is tetrahedral in shape, and is isoelectronic to orthonitrate. The C-O distance is 1.41 Å.[7] is an oxide orthocarbonate (tristrontium orthocarbonate oxide), also stable at atmospheric pressure.[8]

Orthocarbonate esters

The tetravalent moiety 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.[9] Polyorthocarbonates are stable polymers that might have applications in absorbing organic solvents in waste treatment processes,[10] or in dental restorative materials.[11] 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, was synthesized in 2002.[12]

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.[13]

Orthocarbonates may exist in several conformational isomers, 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.[14]

See also

Notes and References

  1. Bohm S. . Antipova D. . Kuthan J. . 1997 . A Study of Methanetetraol Dehydration to Carbonic Acid . International Journal of Quantum Chemistry . 62 . 3 . 315–322 . 10.1002/(SICI)1097-461X(1997)62:3<315::AID-QUA10>3.0.CO;2-8.
  2. http://www.chem.qmul.ac.uk/iupac/class/carba.html#25 Carboxylic Acids and Derivatives
  3. G. Saleh. A. R. Oganov. Novel Stable Compounds in the C-H-O Ternary System at High Pressure. Scientific Reports. 2016. 10.1038/srep32486. 5007508. 27580525. 6. 32486. 2016NatSR...632486S.
  4. Sagatova. Dinara. Shatskiy. Anton. Sagatov. Nursultan. Gavryushkin. Pavel N.. Litasov. Konstantin D.. Calcium orthocarbonate, Ca2CO4-Pnma: A potential host for subducting carbon in the transition zone and lower mantle. Lithos. 370-371. 2020. 105637. 0024-4937. 10.1016/j.lithos.2020.105637. 2020Litho.37005637S. 224909120.
  5. Binck . Jannes . Laniel . Dominique . Bayarjargal . Lkhamsuren . Khandarkhaeva . Saiana . Fedotenko . Timofey . Aslandukov . Andrey . Milman . Victor . Glazyrin . Konstantin . Milman . Victor . Chariton . Stella . Prakapenka . Vitali B. . Dubrovinskaia . Natalia . Dubrovinsky . Leonid . Winkler . Björn . Synthesis of calcium orthocarbonate, Ca2CO4-Pnma at P-T conditions of Earth's transition zone and lower mantle . 2022 . American Mineralogist . 107 . 3 . 336–342 . 10.2138/am-2021-7872. 2022AmMin.107..336B . 242847474 .
  6. Laniel. Dominique. Binck. Jannes. Winkler. Björn. Vogel. Sebastian. Fedotenko. Timofey. Chariton. Stella. Prakapenka. Vitali. Milman. Victor. Schnick. Wolfgang. Dubrovinsky. Leonid. Dubrovinskaia. Natalia. Synthesis, crystal structure and structure–property relations of strontium orthocarbonate, Sr2CO4 . Acta Crystallographica Section B. 77. 1. 2021. 131–137. 2052-5206. 10.1107/S2052520620016650 . 7941283 . 2021AcCrB..77..131L . free.
  7. Spahr . Dominik . Binck . Jannes . Bayarjargal . Lkhamsuren . Luchitskaia . Rita . Morgenroth . Wolfgang . Comboni . Davide . Milman . Victor . Winkler . Björn . Tetrahedrally Coordinated sp3-Hybridized Carbon in Sr2CO4 Orthocarbonate at Ambient Conditions . Inorganic Chemistry . 4 April 2021 . 60 . 8 . 5419–5422 . 10.1021/acs.inorgchem.1c00159. 33813824 . free.
  8. Spahr . Dominik . König . Jannes . Bayarjargal . Lkhamsuren . Gavryushkin . Pavel N. . Milman . Victor . Liermann . Hanns-Peter . Winkler . Björn . Sr 3 [CO 4 ]O Antiperovskite with Tetrahedrally Coordinated sp 3 -Hybridized Carbon and OSr 6 Octahedra . Inorganic Chemistry . 4 October 2021 . 60 . 19 . 14504–14508 . 10.1021/acs.inorgchem.1c01900. 34520201 . 237514625.
  9. http://www.orgsyn.org/orgsyn/orgsyn/prepContent.asp?prep=cv4p0457 Orthocarbonic acid, tetraethyl ester
  10. Sonmez . H.B. . Wudl . F. . 2005 . Cross-linked poly(orthocarbonate)s as organic solvent sorbents . Macromolecules . 38 . 5 . 1623–1626 . 10.1021/ma048731x. 2005MaMol..38.1623S.
  11. Stansbury . J.W. . 1992 . Synthesis and evaluation of new oxaspiro monomers for double ring-opening polymerization . Journal of Dental Research . 71 . 7 . 1408–1412 . 2008-06-19 . 10.1177/00220345920710070901 . 1629456 . 24589493 . dead . https://web.archive.org/web/20080708223634/http://jdr.iadrjournals.org/cgi/content/abstract/71/7/1408 . 2008-07-08.
  12. 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.
  13. 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.
  14. 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.

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