Thiocarbonic acid

Thiocarbonic acid is an inorganic acid which is related to carbonic acid. It is an unstable red oil with the chemical formula H2CS3. It is often referred to as trithiocarbonic acid so as to differentiate it from other thiocarbonates.

Thiocarbonic acid
Names
IUPAC name
carbonotrithioic acid
Other names
Trithiocarbonic acid
Identifiers
3D model (JSmol)
ChEBI
ChemSpider
ECHA InfoCard 100.008.931
EC Number
  • 209-822-6
MeSH C013321
UNII
Properties
CH2S3
Molar mass 110.22 g/mol
Appearance red, oily liquid
Density 1.483 g/cm3(liquid)
Melting point −26.8 °C; −16.3 °F; 246.3 K
Boiling point 58 °C; 136 °F; 331 K
Related compounds
Related compounds
 Carbonic acid, Thiosulfuric acid
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Infobox references

Discovery and synthesis

It was first reported in brief by Zeise in 1824 and later in more detail by Berzelius in 1826,[1] in both cases it was produced by the action of carbon disulfide on a hydrosulfide salt (e.g. potassium hydrosulfide).[2]

CS2 + 2 KSH → K2CS3 + H2S

Treatment with acids liberates the thiocarbonic acid as a red oil

K2CS3 + 2 HX → H2CS3 + 2 KX

Both the acid and many of its salts are unstable and decompose via the release of carbon disulfide, particularly upon heating:

H2CS3 → CS2 + H2S

Applications

Thiocarbonic acid currently has no significant applications. It's esters, which are sometimes called thioxanthates, find use in RAFT polymerization.

References
  1. Berzelius, J. J. (1826). "Ueber die Schwefelsalze" [About the sulfur salts]. Annalen der Physik (in German). 82 (4): 425–458. doi:10.1002/andp.18260820404.
  2. O'Donoghue, Ida Guinevere; Kahan, Zelda (1906). "CLXXIV.—Thiocarbonic acid and some of its salts". J. Chem. Soc., Trans. 89: 1812–1818. doi:10.1039/CT9068901812.
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