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{{Short description|Hypothetical compound with formula C(OH)4}} |
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{{Redirect|Carbon hydroxide|the {{chem2|C(OH)2}} free radical|Dihydroxymethylidene}} |
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| ImageFileL1 = Orthocarbonic acid Structural Formulae.png |
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| ImageFileL1_Ref = {{Chemboximage|correct|??}} |
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|verifiedrevid = 457794250 |
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|ImageFileL1 = Orthocarbonic acid Structural Formulae.png |
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| ImageNameL1 = Stereo skeletal formula of orthocarbonic acid |
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|ImageFileL1_Ref = {{Chemboximage|correct|??}} |
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| ImageFileR1 = Orthocarbonic-acid-Spartan-MP2-3D-balls-B.png |
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|ImageNameL1 = Stereo skeletal formula of orthocarbonic acid |
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|ImageFileR1 = Orthocarbonic-acid-Spartan-MP2-3D-balls-B.png |
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| ImageNameR1 = Ball and stick model of orthocarbonic acid |
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| IUPACName = orthocarbonic acid |
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| SystematicName = Methanetetrol<ref>{{Cite web|title = Methanetetrol - PubChem Public Chemical Database|url = http://pubchem.ncbi.nlm.nih.gov/summary/summary.cgi?cid=9547954&loc=ec_rcs|work = The PubChem Project|location = USA|publisher = National Center for Biotechnology Information}}</ref> (substitutive) |
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|ImageNameR1 = Ball and stick model of orthocarbonic acid |
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| Section1 = {{Chembox Identifiers |
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|PIN = Methanetetrol<ref>{{Cite web|title = Methanetetrol - PubChem Public Chemical Database|url = https://pubchem.ncbi.nlm.nih.gov/summary/summary.cgi?cid=9547954&loc=ec_rcs|work = The PubChem Project|location = USA|publisher = National Center for Biotechnology Information}}</ref> |
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| CASNo = <!-- blanked - oldvalue: 463-84-3 --> |
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|SystematicName = Orthocarbonic acid |
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| PubChem = 9547954 |
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|OtherNames = {{ubl|Carbon tetrahydroxide}} |
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| PubChem_Ref = {{Pubchemcite|correct|pubchem}} |
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|Section1 = {{Chembox Identifiers |
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| ChemSpiderID = 7826887 |
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| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}} |
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|CASNo_Ref = {{cascite|correct|CAS}} |
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|CASNo = 463-84-3 |
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| SMILES = OC(O)(O)O |
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|PubChem = 9547954 |
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| StdInChI = 1S/CH4O4/c2-1(3,4)5/h2-5H |
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|ChemSpiderID = 7826887 |
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| StdInChI_Ref = {{stdinchicite|correct|chemspider}} |
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|ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}} |
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| StdInChIKey = RXCVUXLCNLVYIA-UHFFFAOYSA-N |
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|SMILES = OC(O)(O)O |
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| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}} |
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|StdInChI = 1S/CH4O4/c2-1(3,4)5/h2-5H |
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|StdInChI_Ref = {{stdinchicite|correct|chemspider}} |
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|StdInChIKey = RXCVUXLCNLVYIA-UHFFFAOYSA-N |
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|StdInChIKey_Ref = {{stdinchicite|correct|chemspider}} |
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| Section2 = {{Chembox Properties |
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|Section2 = {{Chembox Properties |
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|Formula = {{chem2|C(OH)4}} |
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| C = 1 |
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| H = 4 |
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|C=1 | H=4 | O=4 |
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| O = 4 |
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| ExactMass = 80.010958616 g mol<sup>-1</sup> |
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|OtherCompounds = {{ubl|]|]|]|]|]}} |
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| OtherCpds = ]<br /> |
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|OtherCations= {{ubl|]|]|]|]|]|]|]|]|]|]|]|]|]|]|]|]}} |
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'''Orthocarbonic acid''' or '''methanetetraol''' is the name given to a hypothetical compound with the ] H<sub>4</sub>CO<sub>4</sub> or C(OH)<sub>4</sub>. Its molecular structure consists of a single ] bonded to four ] groups. It would be therefore a fourfold ]. In theory it could lose four ] to give the hypothetical ] CO<sub>4</sub><sup>4−</sup> ('''orthocarbonate'''), and is therefore considered an ] of carbon. |
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'''Orthocarbonic acid''', '''carbon hydroxide''', '''methanetetrol''' is the name given to a ] with the ] {{chem2|H4CO4}} or {{chem2|C(OH)4}}. Its molecular structure consists of a single ] bonded to four ] groups. It would be therefore a fourfold ]. In theory it could lose four ] to give the hypothetical ] '''orthocarbonate''' {{chem2|CO4(4-)}}, and is therefore considered an ] of carbon. |
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The compound is believed to be highly unstable, decomposing spontaneously into ] monohydrate.<ref name=Bohm1997>S. Bohm, D. Antipova, J. Kuthan (1997) "A Study of Methanetetraol Dehydration to Carbonic Acid". ''International Journal of Quantum Chemistry'', volume 62, pages 315–322 {{doi|10.1002/(SICI)1097-461X(1997)62:3<315::AID-QUA10>3.3.CO;2-N}}</ref><ref> IUPAC Recommendations on Organic & Biochemical Nomenclature</ref> |
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Orthocarbonic acid is highly unstable. Calculations show that it decomposes into ] and water:<ref name=Bohm1997>{{cite journal |author1=Bohm S. |author2=Antipova D. |author3=Kuthan J. | year = 1997 | title = A Study of Methanetetraol Dehydration to Carbonic Acid | journal = International Journal of Quantum Chemistry | volume = 62 |issue=3 | pages = 315–322 | doi =10.1002/(SICI)1097-461X(1997)62:3<315::AID-QUA10>3.0.CO;2-8}}</ref><ref> {{Webarchive|url=https://web.archive.org/web/20170913060101/http://www.chem.qmul.ac.uk/iupac/class/carba.html#25 |date=2017-09-13}} IUPAC Recommendations on Organic & Biochemical Nomenclature</ref> |
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:{{chem2|H4CO4 → H2CO3 + H2O}} |
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Orthocarbonic acid is one of the group of '']s'' that have the general structure of {{chem2|RC(OH)3}}. The term ''ortho acid'' is also used to refer to the most hydroxylated acid in a set of ]s. |
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Researchers predict that orthocarbonic acid is stable at high pressure; hence it may form in the interior of the ] planets ] and ], where water and ] are common.<ref name="Saleh-Scirep">{{cite journal|author1=G. Saleh|author2=A. R. Oganov|title=Novel Stable Compounds in the C-H-O Ternary System at High Pressure|journal=Scientific Reports|date=2016|doi=10.1038/srep32486|pmc=5007508|pmid=27580525|volume=6|page=32486|bibcode=2016NatSR...632486S}}</ref> |
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Orthocarbonic acid is one of the group of ] '']s'' that have the general structure of RC(OH)<sub>3</sub>.The term ''ortho acid'' is also used to refer to the most hydroxylated acid in a set of ]s. |
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==Orthocarbonate anions== |
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==Orthocarbonate anions== |
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By loss of one through 4 protons, orthocarbonic acid could yield four anions: H<sub>3</sub>CO<sub>4</sub><sup>−</sup>, H<sub>2</sub>CO<sub>4</sub><sup>2−</sup>, HCO<sub>4</sub><sup>3−</sup>, and CO<sub>4</sub><sup>4−</sup>. |
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By loss of one through four protons, orthocarbonic acid could yield four anions: {{chem2|H3CO4-}} (trihydrogen orthocarbonate), {{chem2|H2CO4(2-)}} (dihydrogen orthocarbonate), {{chem2|HCO4(3-)}} (hydrogen orthocarbonate), and {{chem2|CO4(4-)}} (orthocarbonate). |
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Numerous ] of fully deprotonated {{chem2|CO4(4-)}}, such as {{chem2|Ca2CO4}} (calcium orthocarbonate) or {{chem2|Sr2CO4}} (strontium orthocarbonate), have been synthesized under high pressure conditions and structurally characterized by X-ray diffraction.<ref name="SagatovaShatskiy2020">{{cite journal|last1=Sagatova|first1=Dinara|last2=Shatskiy|first2=Anton|last3=Sagatov|first3=Nursultan|last4=Gavryushkin|first4=Pavel N.|last5=Litasov|first5=Konstantin D.|title=Calcium orthocarbonate, Ca<sub>2</sub>CO<sub>4</sub>-Pnma: A potential host for subducting carbon in the transition zone and lower mantle|journal=Lithos|volume=370-371|year=2020|pages=105637|issn=0024-4937|doi=10.1016/j.lithos.2020.105637|bibcode=2020Litho.37005637S|s2cid=224909120}}</ref><ref>{{cite journal |last1=Binck |first1=Jannes |last2=Laniel |first2=Dominique |last3=Bayarjargal |first3=Lkhamsuren |last4=Khandarkhaeva |first4=Saiana |last5=Fedotenko |first5=Timofey |last6=Aslandukov |first6=Andrey |last7=Milman |first7=Victor |last8=Glazyrin |first8=Konstantin |last9=Milman |first9=Victor |last10=Chariton |first10=Stella |last11=Prakapenka |first11=Vitali B. |last12=Dubrovinskaia |first12=Natalia |last13=Dubrovinsky |first13=Leonid |last14=Winkler |first14=Björn |title=Synthesis of calcium orthocarbonate, Ca2CO4-Pnma at P-T conditions of Earth's transition zone and lower mantle |date=2022 |journal=American Mineralogist |volume=107 |issue=3 |pages=336–342 |doi=10.2138/am-2021-7872|bibcode=2022AmMin.107..336B |s2cid=242847474 |url=https://bib-pubdb1.desy.de/search?p=id:%22PUBDB-2022-02872%22}}</ref><ref name="LanielBinck2021">{{cite journal|last1=Laniel|first1=Dominique|last2=Binck|first2=Jannes|last3=Winkler|first3=Björn|last4=Vogel|first4=Sebastian|last5=Fedotenko|first5=Timofey|last6=Chariton|first6=Stella|last7=Prakapenka|first7=Vitali|last8=Milman|first8=Victor|last9=Schnick|first9=Wolfgang|last10=Dubrovinsky|first10=Leonid|last11=Dubrovinskaia|first11=Natalia|title=Synthesis, crystal structure and structure–property relations of strontium orthocarbonate, Sr<sub>2</sub>CO<sub>4</sub> |journal=Acta Crystallographica Section B|volume=77|issue=1|year=2021|pages=131–137|issn=2052-5206|doi=10.1107/S2052520620016650 | pmc=7941283 |bibcode=2021AcCrB..77..131L |doi-access=free}}</ref> Strontium orthocarbonate, {{chem2|Sr2CO4}}, is stable at atmospheric pressure. Orthocarbonate is ] in shape, and is isoelectronic to ]. The C-O distance is 1.41 ].<ref>{{cite journal |last1=Spahr |first1=Dominik |last2=Binck |first2=Jannes |last3=Bayarjargal |first3=Lkhamsuren |last4=Luchitskaia |first4=Rita |last5=Morgenroth |first5=Wolfgang |last6=Comboni |first6=Davide |last7=Milman |first7=Victor |last8=Winkler |first8=Björn |title=Tetrahedrally Coordinated sp<sup>3</sup>-Hybridized Carbon in Sr<sub>2</sub>CO<sub>4</sub> Orthocarbonate at Ambient Conditions |journal=Inorganic Chemistry |date=4 April 2021 |volume=60 |issue=8 |pages=5419–5422 |doi=10.1021/acs.inorgchem.1c00159|pmid=33813824 |doi-access=free}}</ref> {{chem2|Sr3(CO4)O}} is an oxide orthocarbonate (tristrontium orthocarbonate oxide), also stable at ].<ref>{{cite journal |last1=Spahr |first1=Dominik |last2=König |first2=Jannes |last3=Bayarjargal |first3=Lkhamsuren |last4=Gavryushkin |first4=Pavel N. |last5=Milman |first5=Victor |last6=Liermann |first6=Hanns-Peter |last7=Winkler |first7=Björn |title=Sr 3 O Antiperovskite with Tetrahedrally Coordinated sp 3 -Hybridized Carbon and OSr 6 Octahedra |journal=Inorganic Chemistry |date=4 October 2021 |volume=60 |issue=19 |pages=14504–14508 |doi=10.1021/acs.inorgchem.1c01900|pmid=34520201 |s2cid=237514625}}</ref> |
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As of 2002, ] of these anions had yet to be observed. However, theoretical studies suggest that Na<sub>4</sub>CO<sub>4</sub> might be stable<ref name=Shema>Musstafa Al-Shemali and Alexander I. Boldyre (2002), "Search for Ionic Orthocarbonates: Ab Initio Study of Na<sub>4</sub>CO<sub>4</sub>". ''J. Phys. Chem. A'', volume 106, issue 38, pages 8951–8954 {{doi|10.1021/jp020207+}}</ref> |
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==Orthocarbonate esters== |
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==Orthocarbonate esters== |
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The ] ] CO<sub>4</sub> is found in stable organic compounds; they are formally ]s of orthocarbonic acid, and therefore are called '''orthocarbonates'''. For example, ] can be prepared by the reaction between ] and ] in ethanol.<ref> ''Organic Syntheses'', Coll. Vol. 4, p.457 (1963); Vol. 32, p.68 (1952)</ref> ]s are stable ]s that might have applications in absorbing organic solvents in waste treatment processes,<ref name=Sonmez2005>{{cite journal | author = Sonmez, H.B. | coauthors = Wudl, F. | year = 2005 | title = Cross-linked poly (orthocarbonate) s as organic solvent sorbents |journal=Macromolecules |volume=38 |issue=5 |pages=1623–1626 |doi=10.1021/ma048731x')}}</ref> or in ].<ref name=Stansbury1992>{{cite journal | author = Stansbury, J.W. | year = 1992 | title = Synthesis and evaluation of new oxaspiro monomers for double ring-opening polymerization | journal = Journal of Dental Research | volume = 71 | issue = 7 | pages = 1408–1412 | url = http://jdr.iadrjournals.org/cgi/content/abstract/71/7/1408 | accessdate = 2008-06-19 | doi = 10.1177/00220345920710070901 | pmid = 1629456}}</ref> |
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The ] ] {{chem2|CO4}} is found in stable ]; they are formally ]s of orthocarbonic acid, and therefore are called '''orthocarbonates'''. For example, ] can be prepared by the reaction between ] and ] in ].<ref> {{Webarchive|url=https://web.archive.org/web/20120920183920/http://www.orgsyn.org/orgsyn/orgsyn/prepContent.asp?prep=cv4p0457 |date=2012-09-20}} ''Organic Syntheses'', Coll. Vol. 4, p. 457 (1963); Vol. 32, p. 68 (1952).</ref> Polyorthocarbonates are stable ]s that might have applications in absorbing ] in ] processes,<ref name=Sonmez2005>{{cite journal | last1 = Sonmez | first1 = H.B. | last2 = Wudl | first2 = F. | year = 2005 | title = Cross-linked poly(orthocarbonate)s as organic solvent sorbents |journal=Macromolecules |volume=38 |issue=5 |pages=1623–1626 |doi=10.1021/ma048731x| bibcode = 2005MaMol..38.1623S}}</ref> or in ].<ref name=Stansbury1992>{{cite journal | last1 = Stansbury | first1 = J.W. | year = 1992 | title = Synthesis and evaluation of new oxaspiro monomers for double ring-opening polymerization | journal = Journal of Dental Research | volume = 71 | issue = 7 | pages = 1408–1412 | url = http://jdr.iadrjournals.org/cgi/content/abstract/71/7/1408 | access-date = 2008-06-19 | doi = 10.1177/00220345920710070901 | pmid = 1629456 | s2cid = 24589493 | url-status = dead | archive-url = https://web.archive.org/web/20080708223634/http://jdr.iadrjournals.org/cgi/content/abstract/71/7/1408 | archive-date = 2008-07-08}}</ref> The explosive ] possesses an orthocarbonate core. |
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A linear polymer which can be described as a (]) ] ester of ], whose formula could be written as {{chem2|_{''n''}|}}, was synthesized in 2002.<ref name=voda2002>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}}</ref> |
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The carbon atom in the spiro ester bis-] orthocarbonate was found to have ] bond geometry, contrasting with the ] geometry of the ] atom in the analogous ] ester.<ref name=meye1979>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}}</ref> |
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Orthocarbonates may exist in several ]s, that differ by the relative rotation of the C–O–C bridges. The conformation structures of some esters, such as ], ], and ] have been determined by ].<ref name=nara1990>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}}</ref> |
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==See also== |
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* ], {{chem2|C(CH2OH)4}} |
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* ], {{chem2|Si(OH)4}} |
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* ], {{chem2|H2CO3}} |
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==References== |
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==References== |
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{{DEFAULTSORT:Orthocarbonic Acid}} |
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