Carbon subsulfide

Carbon subsulfide

Chembox new
Name = 1,2-Propanediene-1,3-dithione
ImageFile =
ImageSize = 250px
ImageName = Carbon subsulfide
OtherNames = Carbon Subsulfide, Tricarbon Disulfide
Section1 = Chembox Identifiers
CASNo = 627-34-9

Section2 = Chembox Properties
Formula = C3S2
MolarMass = 100.162 g/mol
Appearance = red liquid
Density = 1.27
Solubility = insoluble in water
MeltingPt = -1°C
BoilingPt = 90°C

Section3 = Chembox Hazards
RPhrases =
SPhrases =

Carbon Subsulfide is the 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.

ynthesis and structure

C3S2 was discovered by Béla Lengyel, [cite journal
title = Ueber ein neues Kohlenstoffsulfid
journal = Berichte der deutschen chemischen Gesellschaft
volume = 26
year = 1893
pages = 2960-2968
author = B. von Lengyel
doi = 10.1002/cber.189302603124
] who assigned it an unsymmetrical structure. Later, infrared and Raman spectroscopy showed that the structure is symmetrical with a D∞h point group symmetry, [cite journal
title = Infrared and Raman Spectra of Carbon Subsulfide
journal = Journal of Chemical Physics
volume = 45
year = 1966
pages = 1788-1793
author = Smith, W. H., Leroi, G. E.
doi = 10.1063/1.1727828
] 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 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 ℃ as well as flash vacuum pyrolysis (FVP) of 1,2-dithiole-3-thiones. [cite journal
title = The formation of 1,2-propadiene-1,3-dithione from flash vacuum of 1,2-dithiole-3-thiones
journal = Tetrahedron Letters
volume = 27
year = 1996
pages = 4805-4808
author = Pedersen, C. T.
doi = 10.1016/0040-4039(96)00941-0
]

Reactions and occurrence

Among its few known reactions, C3S2 can reacts with bromine to form the cyclic disulfide. [cite journal
title = The chemistry of carbon subsulfide
journal = Sulfur Reports
volume = 21
year = 1999
pages = 423-445
author = Stadlbauer, W., Kappe, T.
] :

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 compound, e.g. the reaction of C3S2 with 2-aminopyridine:

Using microwave spectroscopy, small CnS2 clusters have been detected in interstellar medium. [cite journal
title = Sulfur in IRC+10216
journal = Astronomy and Astrophysics
volume = 181
year = 1987
pages = L9-L12
author = Cernicharo, J., Guelin, M., Hein, H., Kahane, C.
] The rotational transitions of these small carbon sulfides molecules matched with the corresponding molecules.

References


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