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Trithiocarbonic acid
Names
IUPAC name
Carbonotrithioic acid
Systematic IUPAC name
Trithiocarbonic acid
Other names
Thiocarbonic acid
Sulfocarbonic acid
Trisulfocarbonic acid
Dithiocarbon sulfide
Identifiers
3D model (JSmol)
ChEBI
ChemSpider
ECHA InfoCard 100.008.931 Edit this at Wikidata
EC Number
  • 209-822-6
MeSH C013321
UNII
  • InChI=1S/CH2S3/c2-1(3)4/h(H2,2,3,4) ☒N
    Key: HIZCIEIDIFGZSS-UHFFFAOYSA-N ☒N
  • C(=S)(S)S
Properties
H2CS3
Molar mass 110.21 g·mol−1
Appearance Red oily liquid, yellow solid
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
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Thiocarbonic acid is an inorganic acid with the chemical formula H2CS3 (or S=C(SH)2). It is an analog of carbonic acid H2CO3 (or O=C(OH)2), in which all oxygen atoms are replaced with sulfur atoms. It is an unstable hydrophobic red oily liquid.[1]

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 S=C(OH)2, monothiocarbonic O,S-acid O=C(OH)(SH), dithiocarbonic O,S-acid S=C(OH)(SH) and dithiocarbonic S,S-acid O=C(SH)2 (see thiocarbonates).

Discovery and synthesis[edit]

It was first reported in brief by Zeise in 1824 and later in more detail by Berzelius in 1826,[2] in both cases it was produced by the action of carbon disulfide on a hydrosulfide salt (e.g. potassium hydrosulfide).[3]

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

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.[1]

Despite its lability, crystals of thiocarbonic acid have been examined by X-ray crystallography, which confirms the anticipated molecular structure of a trigonal–planar central carbon atom. The C-S bond lengths range from 1.69 to 1.77 Å.[4]

Reactions and derivatives[edit]

Thiocarbonic acid is acidic, with the first pKa being −2.3. The second pKa is near 7. It dissolves S8, but does not react with it.[1]

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 (S=CS2(CH2)2). Oxalyl chloride gives oxalyl trithiocarbonate (S=CS2(C=O)2).

Applications[edit]

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

References[edit]

  1. ^ a b c Gattow, Gerhard; Behrendt, Werner (1977). Carbon Sulfides and their Inorganic and Complex Chemistry. Stuttgart: Georg Thieme. p. 154-6. ISBN 3135262014.
  2. ^ 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.
  3. ^ 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.
  4. ^ Krebs, B.; Gattow, G. (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. 340 (5–6): 294–311. doi:10.1002/zaac.19653400508.
source: https://en.wikipedia.org/wiki/Thiocarbonic_acid

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