Carbon subsulfide

Carbon subsulfide is an inorganic chemical compound with the formula C3S2. This deep red liquid is immiscible with water but soluble in organic solvents. It readily polymerizes at room temperature to form a hard black solid.

Carbon subsulfide
Full structural formula of carbon subsulfide
Space-filling model of the carbon subsulfide molecule
Names
IUPAC name
1,2-Propadiene-1,3-dithione
Other names
Carbon Subsulfide, Tricarbon Disulfide
Identifiers
3D model (JSmol)
ChemSpider
Properties
C3S2
Molar mass 100.15 g·mol−1
Appearance red liquid
Density 1.27 g cm−3
Melting point −1 °C (30 °F; 272 K)
Boiling point 90 °C (194 °F; 363 K)
insoluble
Related compounds
Related compounds
Carbon suboxide
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).

Synthesis and structure

C3S2 was discovered by Béla Lengyel,[1] who assigned it an unsymmetrical structure. Later, infrared and Raman spectroscopy showed that the structure is symmetrical with a D∞h point group symmetry,[2] i.e. S=C=C=C=S. This compound is analogous to carbon suboxide whose structure is O=C=C=C=O.

Lengyel first synthesized this compound by passing carbon disulfide (CS2) vapor through an electric arc with carbon electrodes. This treatment produced a black solution that after filtration and evaporation gave a cherry-red liquid. He determined the molecular mass by cryoscopy. Later preparations of C3S2 include thermolysis of a stream of CS2 in a quartz tube heated to 900 to 1100 °C as well as flash vacuum pyrolysis (FVP) of 1,2-dithiole-3-thiones.[3]

Reactions and occurrence

Among its few known reactions, C3S2 reacts with bromine to form the cyclic disulfide.[4]

C3S2 polymerizes under applied pressure to give a black semi-conducting solid. A similar pressure-induced polymerization of CS2 also gives a black semiconducting polymer.

In addition, reactions of C3S2 can yield highly condensed sulfur-containing compounds, e.g. the reaction of C3S2 with 2-aminopyridine.

Using microwave spectroscopy, small CnS2 clusters have been detected in interstellar medium.[5] The rotational transitions of these molecular carbon sulfides matched with the corresponding molecules.

References

  1. ^ von Lengyel, B. (1893). "Ueber ein neues Kohlenstoffsulfid". Berichte der Deutschen Chemischen Gesellschaft. 26 (3): 2960–2968. doi:10.1002/cber.189302603124.
  2. ^ Smith, W. H.; Leroi, G. E. (1966). "Infrared and Raman Spectra of Carbon Subsulfide". The Journal of Chemical Physics. 45 (5): 1778–1783. Bibcode:1966JChPh..45.1778S. doi:10.1063/1.1727828.
  3. ^ Pedersen, C. T. (1996). "The formation of 1,2-propadiene-1,3-dithione (carbon subsulfide) from flash vacuum pyrolysis of 1,2-dithiole-3-thiones". Tetrahedron Letters. 37 (27): 4805–4808. doi:10.1016/0040-4039(96)00941-0.
  4. ^ Stadlbauer, W.; Kappe, T. (1999). "The Chemistry of Carbon Subsulfide". Sulfur Reports. 21 (4): 423–445. doi:10.1080/01961779908047951.
  5. ^ Cernicharo, J.; Guelin, M.; Hein, H.; Kahane, C. (1987). "Sulfur in IRC + 10216". Astronomy and Astrophysics. 181 (1): L9–L12. Bibcode:1987A&A...181L...9C. ISSN 0004-6361.
Carbon disulfide

Carbon disulfide is a colorless volatile liquid with the formula CS2. The compound is used frequently as a building block in organic chemistry as well as an industrial and chemical non-polar solvent. It has an "ether-like" odor, but commercial samples are typically contaminated with foul-smelling impurities.

Carbon suboxide

Carbon suboxide, or tricarbon dioxide, is an oxide of carbon with chemical formula C3O2 or O=C=C=C=O. Its four cumulative double bonds make it a cumulene. It is one of the stable members of the series of linear oxocarbons O=Cn=O, which also includes carbon dioxide (CO2) and pentacarbon dioxide (C5O2). Although if carefully purified it can exist at room temperature in the dark without decomposing, it will polymerize under certain conditions.

The substance was discovered in 1873 by Benjamin Brodie by subjecting carbon monoxide to an electric current. He claimed that the product was part of a series of "oxycarbons" with formulas Cx+1Ox, namely C2O, C3O2, C4O3, C5O4, ..., and to have identified the last two; however only C3O2 is known. In 1891 Marcellin Berthelot observed that heating pure carbon monoxide at about 550 °C created small amounts of carbon dioxide but no trace of carbon, and assumed that a carbon-rich oxide was created instead, which he named "sub-oxide". He assumed it was the same product obtained by electric discharge and proposed the formula C2O. Otto Diels later stated that the more organic names dicarbonylmethane and dioxallene were also correct.

It is commonly described as an oily liquid or gas at room temperature with an extremely noxious odor.

Carbon sulfide

Carbon sulfide may refer to:

Carbon disulfide

Carbon monosulfide

Carbon subsulfide

Sulflower

Thioketene

Thioketenes are organosulfur compounds analogous to ketenes with the general formula R2C=C=S, where R is alkyl or aryl. Thioketene (ethenthione) is also the name of the compound CH2=C=S, which is the simplest thioketene. Thioketenes are reactive, tending to polymerize. Some thioketenes are produced as transient species upon pyrolysis of 1,2,3-thiadiazoles.Bis(trifluoromethyl)thioketene ((CF3)2C=C=S) is a rare example of a stable thioketene. Another stable thioketene is carbon subsulfide (S=C=C=C=S).

Sulfur compounds
Compounds
Carbon ions
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