Dicarbonate

Dicarbonate ion
Names
	IUPAC name Dicarbonate
	Other names Pyrocarbonate
Identifiers
CAS Number	214335-04-3 ;
3D model (JSmol)	Interactive image;
MeSH	pyrocarbonate
PubChem CID	15238643;
CompTox Dashboard (EPA)	DTXSID30570367;
	InChI InChI=1S/C2H2O5/c3-1(4)7-2(5)6/h(H,3,4)(H,5,6)/p-2 Key: ZFTFAPZRGNKQPU-UHFFFAOYSA-L;
	SMILES C(=O)([O-])OC(=O)[O-];
Properties
Chemical formula	C2O2−5
Molar mass	104.017 g·mol−1
	Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). Infobox references

Molecular structure of bis(trifluoromethyl) dicarbonate^[1]

A dicarbonate, also known as a pyrocarbonate, is a chemical containing the divalent −O−C(=O)−O−C(=O)−O− or −C₂O₅− functional group, which consists of two carbonate groups sharing an oxygen atom. It is one of polycarbonate functional groups. These compounds can be viewed as derivatives of the hypothetical compound dicarbonic acid,^[2] HO−C(=O)−O−C(=O)−OH or H₂C₂O₅. Three important organic compounds containing this group are:

dimethyl dicarbonate H₃C−C₂O₅−CH₃
diethyl dicarbonate C₂H₅−C₂O₅−C₂H₅
di-tert-butyl dicarbonate (H₃C−)₃C−C₂O₅−C(−CH₃)₃, also known as Boc anhydride.

It is one of the oxocarbon anions, consisting solely of oxygen and carbon. The anion has the formula ⁻O−C(=O)−O−C(=O)−O⁻ or C₂O2−5. Dicarbonate salts are apparently unstable at ambient conditions, but can be made under pressure and may have a fleeting existence in carbonate solutions.^[3]

The term dicarbonate is sometimes used erroneously to refer to bicarbonate, the common name of the hydrogencarbonate anion HCO−3 or esters of the hydrogencarbonate functional group −O−C(=O)−OH. It is also sometimes used for chemicals that contain two carbonate units in their covalent structure or stoichiometric formula.

^ Plácido García; Helge Willner; Maximiliano Burgos Paci; Gustavo A. Argüello; Thorsten Berends (2005). "Bis(trifluoromethyl)dicarbonate, CF₃OC(O)OC(O)OCF₃". J. Fluorine Chem. 126 (6): 984–990. doi:10.1016/j.jfluchem.2005.05.002.
^ "CHEBI:48501 - dicarbonic acid". ChEBI. Retrieved 30 June 2024.
^ Zeller, Klaus-Peter; Schuler, Paul; Haiss, Peter (2005). "The hidden equilibrium in aqueous sodium carbonate solutions: Evidence for the formation of the dicarbonate anion". Eur. J. Inorg. Chem. 2005 (1): 168–172. doi:10.1002/ejic.200400445.

[1] Plácido García; Helge Willner; Maximiliano Burgos Paci; Gustavo A. Argüello; Thorsten Berends (2005). "Bis(trifluoromethyl)dicarbonate, CF₃OC(O)OC(O)OCF₃". J. Fluorine Chem. 126 (6): 984–990. doi:10.1016/j.jfluchem.2005.05.002.

[2] "CHEBI:48501 - dicarbonic acid". ChEBI. Retrieved 30 June 2024.

[3] Zeller, Klaus-Peter; Schuler, Paul; Haiss, Peter (2005). "The hidden equilibrium in aqueous sodium carbonate solutions: Evidence for the formation of the dicarbonate anion". Eur. J. Inorg. Chem. 2005 (1): 168–172. doi:10.1002/ejic.200400445.

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