Thiocarbonic acid: Difference between revisions
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|Section2={{Chembox Properties |
|Section2={{Chembox Properties |
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| Formula = CH<sub>2</sub>S<sub>3</sub> |
| Formula = CH<sub>2</sub>S<sub>3</sub> |
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| C=1|H=2|S=3 |
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| MolarMass = 110.22 g/mol |
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| Appearance = Red oil, yellow solid |
| Appearance = Red oil, yellow solid |
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| Density = 1.483 g/cm<sup>3</sup>(liquid) |
| Density = 1.483 g/cm<sup>3</sup>(liquid) |
Revision as of 14:01, 3 August 2023
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Names | |
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IUPAC name
Carbonotrithioic acid
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Systematic IUPAC name
Trithiocarbonic acid | |
Other names
Thiocarbonic acid
Sulfocarbonic acid Trisulfocarbonic acid Dithiocarbon sulfide | |
Identifiers | |
3D model (JSmol)
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ChEBI | |
ChemSpider | |
ECHA InfoCard | 100.008.931 |
EC Number |
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MeSH | C013321 |
PubChem CID
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UNII | |
CompTox Dashboard (EPA)
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Properties | |
CH2S3 | |
Molar mass | 110.21 g·mol−1 |
Appearance | Red oil, 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
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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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Thiocarbonic acid is an inorganic acid which 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 with the chemical formula H2CS3 (or S=C(SH)2).[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
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
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]
It reacts with bifunctional reagents to give rings. 1,2-Dichloroethane gives ethylene trithiocarbonate (SCS2C2H4). Oxalyl chloride gives oxalotrithiocarbonate (SCS2(CO)2).
Applications
Thiocarbonic acid currently has no significant applications. Its esters, which are sometimes called thioxanthates, find use in RAFT polymerization.
References
- ^ a b c Gattow, Gerhard; Behrendt, Werner (1977). Carbon Sulfides and their Inorganic and Complex Chemistry. Stuttgart: Georg Thieme. p. 154-6. ISBN 3135262014.
- ^ 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.
- ^ 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.