Thiocarbonic acid

Thiocarbonic acid
Names
	IUPAC name carbonotrithioic acid
	Other names Trithiocarbonic acid
Identifiers
CAS Number	594-08-1 ;
3D model (JSmol)	Interactive image;
ChEBI	CHEBI:36967 ;
ChemSpider	62204 ;
ECHA InfoCard	100.008.931
EC Number	209-822-6;
MeSH	C013321
PubChem CID	68982;
UNII	O27JHO40J8 ;
	InChI InChI=1S/CH2S3/c2-1(3)4/h(H2,2,3,4) Key: HIZCIEIDIFGZSS-UHFFFAOYSA-N ;
	SMILES C(=S)(S)S;
Properties
Chemical formula	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). verify (what is ?) Infobox references

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.

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. Its esters, which are sometimes called thioxanthates, find use in RAFT polymerization.

References

Berzelius, J. J. (1826). "Ueber die Schwefelsalze" [About the sulfur salts]. Annalen der Physik (in German). 82 (4): 425–458. Bibcode:1826AnP....82..425B. doi:10.1002/andp.18260820404.
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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[1] Berzelius, J. J. (1826). "Ueber die Schwefelsalze" [About the sulfur salts]. Annalen der Physik (in German). 82 (4): 425–458. Bibcode:1826AnP....82..425B. 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.