原碳酸

原碳酸
Stereo skeletal formula of orthocarbonic acid	Ball and stick model of orthocarbonic acid
	IUPAC名; Methanetetrol; 甲四醇
識別
CAS號	463-84-3
PubChem	9547954
ChemSpider	7826887
SMILES	OC(O)(O)O;
性質
化學式	CH4O4
摩爾質量	80.04 g·mol−1
相關物質
相關化學品	二羥基亞甲基卡賓; 矽酸
	若非註明，所有數據均出自標準狀態（25 ℃，100 kPa）下。

原碳酸是一種假想的酸，化學式H₄CO₄。在一個原碳酸分子中，碳原子與4個羥基以共價鍵相連，因此是一種四醇。理論上，原碳酸可以離解四個氫離子，生成假想的碳氧陰離子（英語：oxocarbon anion） CO4−
4（原碳酸根），因此也是碳的一種含氧酸。

Quick Facts 原碳酸, 識別 ...

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這種化合物至今未被發現，因為它極不穩定，會立刻分解為碳酸和水。^[2]^[3]

H₄CO₄ → H₂CO₃ + H₂O

原碳酸可能在高壓下穩定，因此可能存在於含有大量水和甲烷的冰巨行星天王星和海王星內部。^[4]

原碳酸鹽

原碳酸是四元酸，可以解離成四種原碳酸根，分別是H
3CO−
4、H
2CO2−
4、HCO3−
4和CO4−
4。

在高壓下可以合成CO4−
4的鹽，如Ca
2CO
4和Sr
2CO
4，其結構已通過X射線繞射確定。^[5]^[6]原碳酸鍶 Sr
2CO
4在常壓下穩定，其中的原碳酸根呈四面體形分子構型，C-O鍵長1.41 Å。^[7]類似的Sr
3[CO
4]O也可以在常壓下穩定存在。^[8]

原碳酸酯

原碳酸可以形成酯。例如，它可以形成原碳酸四乙酯，可以用三氯硝基甲烷和乙醇鈉在乙醇中製取。^[9] 另外，聚原碳酸酯是穩定的，可以用於吸收污水中的有機溶劑，^[10]或用於牙科還原材料。^[11]

參考

[1]
Methanetetrol - PubChem Public Chemical Database. The PubChem Project. USA: National Center for Biotechnology Information. [2022-12-08]. （原始內容存檔於2012-11-03）.
[2]
Bohm, S.; Antipova, D.; Kuthan, J. A Study of Methanetetraol Dehydration to Carbonic Acid. International Journal of Quantum Chemistry. 1997, 62: 315–322. doi:10.1002/(SICI)1097-461X(1997)62:3<315::AID-QUA10>3.3.CO;2-N.
[3]
Carboxylic Acids and Derivatives 互聯網檔案館的存檔，存檔日期2017-09-13. IUPAC Recommendations on Organic & Biochemical Nomenclature
[4]
G. Saleh; A. R. Oganov. Novel Stable Compounds in the C-H-O Ternary System at High Pressure. Scientific Reports. 2016, 6: 32486. Bibcode:2016NatSR...632486S. PMC 5007508 . PMID 27580525. doi:10.1038/srep32486.
[5]
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. 2020,. 370-371: 105637. Bibcode:2020Litho.37005637S. ISSN 0024-4937. S2CID 224909120. doi:10.1016/j.lithos.2020.105637.
[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. 2021, 77 (1): 131–137. ISSN 2052-5206. PMC 7941283 . doi:10.1107/S2052520620016650 .
[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. PMID 33813824. doi:10.1021/acs.inorgchem.1c00159 .
[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. PMID 34520201. S2CID 237514625. doi:10.1021/acs.inorgchem.1c01900.
[9]
ETHYL ORTHOCARBONATE. Organic Syntheses (Organic Syntheses). 1952, 32: 68. ISSN 0078-6209. doi:10.15227/orgsyn.032.0068.
[10]
Sonmez, H.B.; Wudl, F. Cross-linked poly (orthocarbonate) s as organic solvent sorbents. Macromolecules. 2005, 38 (5): 1623–1626. doi:10.1021/ma048731x').
[11]
Stansbury, J.W. Synthesis and evaluation of new oxaspiro monomers for double ring-opening polymerization. Journal of Dental Research. 1992, 71 (7): 1408–1412 [2008-06-19]. doi:10.1177/00220345920710070901. （原始內容存檔於2008-07-08）.

[1] [1]
Methanetetrol - PubChem Public Chemical Database. The PubChem Project. USA: National Center for Biotechnology Information. [2022-12-08]. （原始內容存檔於2012-11-03）.

[Bohm1997-2] [2]
Bohm, S.; Antipova, D.; Kuthan, J. A Study of Methanetetraol Dehydration to Carbonic Acid. International Journal of Quantum Chemistry. 1997, 62: 315–322. doi:10.1002/(SICI)1097-461X(1997)62:3<315::AID-QUA10>3.3.CO;2-N.

[3] [3]
Carboxylic Acids and Derivatives 互聯網檔案館的存檔，存檔日期2017-09-13. IUPAC Recommendations on Organic & Biochemical Nomenclature

[Saleh-Scirep-4] [4]
G. Saleh; A. R. Oganov. Novel Stable Compounds in the C-H-O Ternary System at High Pressure. Scientific Reports. 2016, 6: 32486. Bibcode:2016NatSR...632486S. PMC 5007508 . PMID 27580525. doi:10.1038/srep32486.

[SagatovaShatskiy2020-5] [5]
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. 2020,. 370-371: 105637. Bibcode:2020Litho.37005637S. ISSN 0024-4937. S2CID 224909120. doi:10.1016/j.lithos.2020.105637.

[LanielBinck2021-6] [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. 2021, 77 (1): 131–137. ISSN 2052-5206. PMC 7941283 . doi:10.1107/S2052520620016650 .

[7] [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. PMID 33813824. doi:10.1021/acs.inorgchem.1c00159 .

[8] [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. PMID 34520201. S2CID 237514625. doi:10.1021/acs.inorgchem.1c01900.

[9] [9]
ETHYL ORTHOCARBONATE. Organic Syntheses (Organic Syntheses). 1952, 32: 68. ISSN 0078-6209. doi:10.15227/orgsyn.032.0068.

[Sonmez2005-10] [10]
Sonmez, H.B.; Wudl, F. Cross-linked poly (orthocarbonate) s as organic solvent sorbents. Macromolecules. 2005, 38 (5): 1623–1626. doi:10.1021/ma048731x').

[Stansbury1992-11] [11]
Stansbury, J.W. Synthesis and evaluation of new oxaspiro monomers for double ring-opening polymerization. Journal of Dental Research. 1992, 71 (7): 1408–1412 [2008-06-19]. doi:10.1177/00220345920710070901. （原始內容存檔於2008-07-08）.

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