Dicarbonate

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Not to be confused with Bicarbonate.
Dicarbonate
Dicarbonate-ester-2D.png
Names
IUPAC name
Carboxylato carbonate
Other names
Pyrocarbonate
Identifiers
3D model (JSmol)
MeSH pyrocarbonate
  • InChI=1S/C2H2O5/c3-1(4)7-2(5)6/h(H,3,4)(H,5,6)/p-2
    Key: ZFTFAPZRGNKQPU-UHFFFAOYSA-L
  • C(=O)([O-])OC(=O)[O-]
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).
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
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.

It is one of the oxocarbon anions, consisting solely of oxygen and carbon. Dicarbonate salts are apparently unstable at ambient conditions, but can be made under pressure and 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.

Inorganic salts

PbC2O5 can be formed at 30 GPa and 2000K from PbCO3 and CO2. It forms white monoclinic crystals, with space group P21/c and four formula units per unit cell. At 30 GPa the unit cell has a=4.771 b=8.079 c=7.070 Å and β=91.32°. The unit cell volume is 272.4 Å3 and density 7.59.[3]

SrC2O5 is very similar to the lead compound, and also has monoclinic structure with space group P21/c and four formula units per unit cell. At 30 GPa the unit cell has a=4.736 b=8.175 c=7.140 Å and β=91.34°. The unit cell volume is 276.3 Å3 and density 4.61.[3] The double Sr=O bonds have lengths of 1.22, 1.24, and 1.25 Å. The single Sr-O bonds have lengths of 1.36 and 1.41 Å. The angles subtended at the carbon atoms are slightly less than 120°, and the angle at the C-O-C is larger.[4]

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 (6): 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.
  3. ^ a b Spahr, Dominik; König, Jannes; Bayarjargal, Lkhamsuren; Luchitskaia, Rita; Milman, Victor; Perlov, Alexander; Liermann, Hanns-Peter; Winkler, Björn (22 June 2022). "Synthesis and Structure of Pb[C2O5]: An Inorganic Pyrocarbonate Salt". Inorganic Chemistry: acs.inorgchem.2c01507. doi:10.1021/acs.inorgchem.2c01507.
  4. ^ Spahr, Dominik; König, Jannes; Bayarjargal, Lkhamsuren; Milman, Victor; Perlov, Alexander; Liermann, Hanns-Peter; Winkler, Björn (23 February 2022). "Sr[C2O5 ] is an Inorganic Pyrocarbonate Salt with [C 2 O 5 ] 2– Complex Anions". Journal of the American Chemical Society. 144 (7): 2899–2904. doi:10.1021/jacs.2c00351.
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