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Thiocarbonic acid

| NFPA-H = | NFPA-F = | NFPA-R = | NFPA-S = Thiocarbonic acid is an acid with the chemical formula (or ). It is an analog of carbonic acid (or ), in which all oxygen atoms are replaced with sulfur atoms. It is an unstable hydrophobic red oily liquid.

It is often referred to as trithiocarbonic acid so as to differentiate it from other carbonic acids containing sulfur, such as monothiocarbonic O,O-acid , monothiocarbonic O,S-acid , dithiocarbonic O,S-acid and dithiocarbonic S,S-acid (see thiocarbonates).

Discovery and synthesis

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

Treatment with acids liberates the thiocarbonic acid as a red oil: :

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

An improved synthesis involves addition of barium trithiocarbonate to hydrochloric acid at 0 °C. This method provided samples with which many measurement have been made. :

Despite its lability, crystals of thiocarbonic acid have been examined by X-ray crystallography, which confirms the anticipated molecular structure of a trigonal planar molecular geometry at the central carbon atom. The C-S bond lengths range from 1.69 to 1.77 Å.

Reactions and derivatives

Thiocarbonic acid is acidic, with the first pKa being around 2. The second pKa is near 7. It dissolves , but does not react with it.

Salts and esters of trithiocarbonic acid are called trithiocarbonates, and they are sometimes called thioxanthates.

Thiocarbonic acid reacts with bifunctional reagents to give rings. 1,2-Dichloroethane gives ethylene trithiocarbonate (). Oxalyl chloride gives oxalyl trithiocarbonate ().

| File:C2H4S2CS.svg | Ethylene trithiocarbonate | File:Oxalyl trithiocarbonate.png | Oxalyl trithiocarbonate | File:Dimethyl trithiocarbonate molecule.png | Dimethyl trithiocarbonate

Applications

Thiocarbonic acid currently has no significant applications. Its esters find use in RAFT polymerization.

References

References

  1. (1977). "Carbon Sulfides and their Inorganic and Complex Chemistry". Georg Thieme.
  2. (1826). "Ueber die Schwefelsalze". Annalen der Physik.
  3. (1906). "CLXXIV.—Thiocarbonic acid and some of its salts". J. Chem. Soc., Trans..
  4. (1965). "Über Chalkogenocarbonate. XIV. Das Kohlenstoffsulfid-bis-(hydrogensulfid) SC(SH)2 und das System H2S−CS2 6. Die Kristallstruktur der Trithiokohlensure bei -100 ″C". Zeitschrift für anorganische und allgemeine Chemie.
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hydrogen-compounds sulfur(−ii)-compounds inorganic-carbon-compounds
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