Dicarbonate

In organic chemistry, a dicarbonate, also known as a pyrocarbonate, is a compound containing the divalent [−O−(C=O)−O−(C=O)−O−] or −C
2O
5− functional group, which consists of two carbonate groups sharing an oxygen atom. These compounds can be viewed as double esters of a hypothetical dicarbonic acid, H
2C
2O
5 or HO−(C=O)−O−(C=O)−OH. Two important examples are dimethyl dicarbonate H3C−C2O5−CH3 and di-tert-butyl dicarbonate (H3C−)3C−C2O5−C(−CH3)3.

Dicarbonate
Names
IUPAC name
Carboxylato carbonate
Other names
Pyrocarbonate
Identifiers
3D model (JSmol)
MeSH pyrocarbonate
Properties
C2O5-2 (Basic formula)
Molar mass 104.02 g/mol
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
Infobox references
The general structure of dicarbonates
Crystal structure of bis(trifluoromethyl) dicarbonate[1]
Not to be confused with Bicarbonate.

It is one of the oxocarbon anions, consisting solely of oxygen and carbon. Dicarbonate salts are apparently unstable but may have a fleeting existence in carbonate solutions.[2]

The term "dicarbonate" is sometimes used erroneously to refer to bicarbonate, the common name of the hydrogencarbonate anion HCO−
3 or organic group the ROCO2H.

See also

References
  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: 984–990. doi:10.1016/j.jfluchem.2005.05.002.
  2. 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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