Dicarbonate

From Wikipedia, the free encyclopedia
Jump to: navigation, search
The general structure of dicarbonates
Crystal structure of bis(trifluoromethyl) dicarbonate[1]

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
2
O
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
2
C
2
O
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.

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 HCO3 or organic group the ROCO2H.

See also[edit]

References[edit]

  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.