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Orthocarbonic acid

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"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
  • InChI=1S/CH4O4/c2-1(3,4)5/h2-5H checkY
    Key: RXCVUXLCNLVYIA-UHFFFAOYSA-N checkY
  • OC(O)(O)O
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).
☒N verify (what is checkY☒N ?)

Orthocarbonic acid, carbon hydroxide, methanetetrol is the name given to a hypothetical 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 highly unstable. Calculations show that it decomposes into carbonic acid and water:[2][3]

H4CO4 → H2CO3 + H2O

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.

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.[4] Due to its resemblance to the Swastika, it is commonly known as Hitler's Acid.[5]

Orthocarbonate anions

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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] 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.[9] Sr3(CO4)O is an oxide orthocarbonate (tristrontium orthocarbonate oxide), also stable at atmospheric pressure.[10]

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.[11] Polyorthocarbonates are stable polymers that might have applications in absorbing organic solvents in waste treatment processes,[12] or in dental restorative materials.[13] 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.[14]

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.[15]

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.[16]

See also

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References

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  1. ^ "Methanetetrol - PubChem Public Chemical Database". The PubChem Project. USA: National Center for Biotechnology Information.
  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 Archived 2017-09-13 at the Wayback Machine IUPAC Recommendations on Organic & Biochemical Nomenclature
  4. ^ G. Saleh; A. R. Oganov (2016). "Novel Stable Compounds in the C-H-O Ternary System at High Pressure". Scientific Reports. 6: 32486. Bibcode:2016NatSR...632486S. doi:10.1038/srep32486. PMC 5007508. PMID 27580525.
  5. ^ Williams, Matt (2016-09-09). "Uranus & Neptune May Keep "Hitler's Acid" Stable Under Massive Pressure". Universe Today. Retrieved 2024-12-17.
  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: 105637. Bibcode:2020Litho.37005637S. doi:10.1016/j.lithos.2020.105637. ISSN 0024-4937. S2CID 224909120.
  7. ^ 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 (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. Bibcode:2022AmMin.107..336B. doi:10.2138/am-2021-7872. S2CID 242847474.
  8. ^ Laniel, Dominique; Binck, Jannes; Winkler, Björn; Vogel, Sebastian; Fedotenko, Timofey; Chariton, Stella; Prakapenka, Vitali; Milman, Victor; Schnick, Wolfgang; Dubrovinsky, Leonid; Dubrovinskaia, Natalia (2021). "Synthesis, crystal structure and structure–property relations of strontium orthocarbonate, Sr2CO4". Acta Crystallographica Section B. 77 (1): 131–137. Bibcode:2021AcCrB..77..131L. doi:10.1107/S2052520620016650. ISSN 2052-5206. PMC 7941283.
  9. ^ 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.
  10. ^ 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. S2CID 237514625.
  11. ^ Orthocarbonic acid, tetraethyl ester Archived 2012-09-20 at the Wayback Machine Organic Syntheses, Coll. Vol. 4, p. 457 (1963); Vol. 32, p. 68 (1952).
  12. ^ Sonmez, H.B.; Wudl, F. (2005). "Cross-linked poly(orthocarbonate)s as organic solvent sorbents". Macromolecules. 38 (5): 1623–1626. Bibcode:2005MaMol..38.1623S. doi:10.1021/ma048731x.
  13. ^ 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. S2CID 24589493. Archived from the original on 2008-07-08. Retrieved 2008-06-19.
  14. ^ 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
  15. ^ 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
  16. ^ 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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