Carbon subsulfide

Last updated
Carbon subsulfide
Carbon subsulfide.svg
Carbon subsulfide 3D spacefill.png
Names
Preferred IUPAC name
Propa-1,2-diene-1,3-dithione
Other names
Carbon Subsulfide, Tricarbon Disulfide
Identifiers
3D model (JSmol)
ChemSpider
PubChem CID
  • InChI=1S/C3S2/c4-2-1-3-5 X mark.svgN
    Key: RMCQREAPGZPWGK-UHFFFAOYSA-N X mark.svgN
  • InChI=1/C3S2/c4-2-1-3-5
    Key: RMCQREAPGZPWGK-UHFFFAOYAC
  • S=C=C=C=S
Properties
C3S2
Molar mass 100.15 g·mol−1
Appearancered liquid
Density 1.319 g cm−3 [1]
Melting point −1 °C (30 °F; 272 K)
Boiling point 90 °C (194 °F; 363 K)
insoluble
Related compounds
Related compounds
 Carbon suboxide
Carbon disulfide
Ethenedithione
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
X mark.svgN  verify  (what is  Yes check.svgYX mark.svgN ?)

Carbon subsulfide is an organic, sulfur-containing chemical compound with the formula C3S2 and structure S=C=C=C=S. 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.

Contents

Synthesis and structure

C3S2 was discovered by Béla Lengyel, [2] who assigned it an unsymmetrical structure. Later, infrared and Raman spectroscopy showed that the structure is symmetrical with a D∞h point group symmetry, [3] 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. [4]

Reactions and occurrence

Among its few known reactions, C3S2 reacts with bromine to form the cyclic disulfide. [5]

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. [6] The rotational transitions of these molecular carbon sulfides matched with the corresponding molecules.

Related Research Articles

<span class="mw-page-title-main">Kerogen</span> Solid organic matter in sedimentary rocks

Kerogen is solid, insoluble organic matter in sedimentary rocks. It consists of a variety of organic materials, including dead plants, algae, and other microorganisms, that have been compressed and heated by geological processes. All the kerogen on earth is estimated to contain 1016 tons of carbon. This makes it the most abundant source of organic compounds on earth, exceeding the total organic content of living matter 10,000-fold.

<span class="mw-page-title-main">Carbon disulfide</span> Neurotoxic compound with formula S=C=S

Carbon disulfide is an inorganic compound with the chemical formula CS2 and structure S=C=S. It is also considered as the anhydride of thiocarbonic acid. It is a colorless, flammable, neurotoxic liquid that is used as a building block in organic synthesis. Pure carbon disulfide has a pleasant, ether- or chloroform-like odor, but commercial samples are usually yellowish and are typically contaminated with foul-smelling impurities.

Thiophene is a heterocyclic compound with the formula C4H4S. Consisting of a planar five-membered ring, it is aromatic as indicated by its extensive substitution reactions. It is a colorless liquid with a benzene-like odor. In most of its reactions, it resembles benzene. Compounds analogous to thiophene include furan (C4H4O), selenophene (C4H4Se) and pyrrole (C4H4NH), which each vary by the heteroatom in the ring.

<span class="mw-page-title-main">Polysulfide</span> Molecules derived from sulfur chains

Polysulfides are a class of chemical compounds derived from anionic chains of sulfur atoms. There are two main classes of polysulfides: inorganic and organic. The inorganic polysulfides have the general formula S2−
n. These anions are the conjugate bases of polysulfanes H2Sn. Organic polysulfides generally have the formulae R1SnR2, where R is an alkyl or aryl group.

<span class="mw-page-title-main">Isocyanic acid</span> Chemical compound (H–N=C=O)

Isocyanic acid is a chemical compound with the structural formula HNCO, which is often written as H−N=C=O. It is a colourless, volatile and poisonous substance, with a boiling point of 23.5 °C. It is the predominant tautomer and an isomer of cyanic acid (aka. cyanol).

<span class="mw-page-title-main">Thioketone</span> Organic compounds with the structure >C=S

In organic chemistry, thioketones are organosulfur compounds related to conventional ketones in which the oxygen has been replaced by a sulfur. Instead of a structure of R2C=O, thioketones have the structure R2C=S, which is reflected by the prefix "thio-" in the name of the functional group. Thus the simplest thioketone is thioacetone, the sulfur analog of acetone. Unhindered alkylthioketones typically tend to form polymers or rings.

<span class="mw-page-title-main">Disulfur dichloride</span> Chemical compound

Disulfur dichloride is the inorganic compound of sulfur and chlorine with the formula S2Cl2. It is an amber oily liquid.

<span class="mw-page-title-main">Thiophosgene</span> Chemical compound

Thiophosgene is a red liquid with the formula CSCl2. It is a molecule with trigonal planar geometry. There are two reactive C–Cl bonds that allow it to be used in diverse organic syntheses.

<span class="mw-page-title-main">Dithiane</span> Chemical compound

A dithiane is a heterocyclic compound composed of a cyclohexane core structure wherein two methylene bridges are replaced by sulfur. The three isomeric parent heterocycles are 1,2-dithiane, 1,3-dithiane and 1,4-dithiane. They are all colorless solids.

<span class="mw-page-title-main">Sodium maleonitriledithiolate</span> Chemical compound

Sodium maleonitriledithiolate is the chemical compound described by the formula Na2S2C2(CN)2. The name refers to the cis compound, structurally related to maleonitrile. Maleonitriledithiolate is often abbreviated mnt. It is a "dithiolene", i.e. a chelating alkene-1,2-dithiolate. It is a prototypical non-innocent ligand in coordination chemistry. Several complexes are known, such as Ni(mnt)2]2−.

<span class="mw-page-title-main">Carbon diselenide</span> Chemical compound

Carbon diselenide is an inorganic compound with the chemical formula CSe2. It is a yellow-orange oily liquid with pungent odor. It is the selenium analogue of carbon disulfide and carbon dioxide. This light-sensitive compound is insoluble in water and soluble in organic solvents.

<span class="mw-page-title-main">Thioketene</span> Organic compounds with the structure >C=C=S

In organic chemistry, thioketenes are organosulfur compounds analogous to ketenes with the general formula R2C=C=S, where R is alkyl or aryl. The parent thioketene (ethenthione) has the formula CH2=C=S. It is the simplest thioketene. Thioketene is stable as a gas, but like most thioketenes, it polymerizes upon condensation.

<span class="mw-page-title-main">Thiocarbonic acid</span> Chemical compound

Thiocarbonic acid is an acid with the chemical formula H2CS3. It is an analog of carbonic acid H2CO3, in which all oxygen atoms are replaced with sulfur atoms. It is an unstable hydrophobic red oily liquid.

<span class="mw-page-title-main">Thiophosphoryl fluoride</span> Chemical compound

Thiophosphoryl fluoride is an inorganic molecular gas with formula PSF3 containing phosphorus, sulfur and fluorine. It spontaneously ignites in air and burns with a cool flame. The discoverers were able to have flames around their hands without discomfort, and called it "probably one of the coldest flames known". The gas was discovered in 1888.

<span class="mw-page-title-main">Thioacetone</span> Chemical compound

Thioacetone is an organosulfur compound belonging to the -thione group called thioketones with a chemical formula (CH3)2CS. It is an unstable orange or brown substance that can be isolated only at low temperatures. Above −20 °C (−4 °F), thioacetone readily converts to a polymer and a trimer, trithioacetone. It has an extremely potent, unpleasant odor, and is considered one of the worst-smelling chemicals known to humanity.

<span class="mw-page-title-main">Spiropentane</span> Chemical compound

Spiropentane is a hydrocarbon with formula C5H8. It is the simplest spiro-connected cycloalkane, a triangulane. It took several years after the discovery in 1887 until the structure of the molecule was determined. According to the nomenclature rules for spiro compounds, the systematic name is spiro[2.2]pentane. However, there can be no constitutive isomeric spiropentanes, hence the name is unique without brackets and numbers.

<span class="mw-page-title-main">Mercaptobenzothiazole</span> Chemical compound

2-Mercaptobenzothiazole is an organosulfur compound with the formula C6H4(NH)SC=S. A white solid, it is used in the sulfur vulcanization of rubber.

<span class="mw-page-title-main">Sodium 1,3-dithiole-2-thione-4,5-dithiolate</span> Chemical compound

Sodium 1,3-dithiole-2-thione-4,5-dithiolate is the organosulfur compound with the formula Na2C3S5, abbreviated Na2dmit. It is the sodium salt of the conjugate base of the 4,5-bis(sulfanyl)-1,3-dithiole-2-thione. The salt is a precursor to dithiolene complexes and tetrathiafulvalenes.

<span class="mw-page-title-main">Trithioacetone</span> Chemical compound

Trithioacetone (2,2,4,4,6,6-hexamethyl-1,3,5-trithiane) is an organic chemical with formula C
9H
18S
3. Its covalent structure is [–C(CH
3)
2–S–]
3, that is, a six-membered ring of alternating carbon and sulfur atoms, with two methyl groups attached to each carbon. It can be viewed as a derivative of 1,3,5-trithiane, with methyl-group substituents for all of the hydrogen atoms in that parent structure.

Ethenedithione or ethylenedithone is an unstable chemical substance with formula S=C=C=S made from carbon and sulfur.

References

  1. ↑ Stock, A.; Praetorius, P. (1912). "Zur Kenntnis des Kohlensubsulfids, C3S2". Chemische Berichte. 45 (3): 3568–3578. doi:10.1002/cber.191204503114.
  2. ↑ von Lengyel, B. (1893). "Ueber ein neues Kohlenstoffsulfid". Berichte der Deutschen Chemischen Gesellschaft. 26 (3): 2960–2968. doi:10.1002/cber.189302603124.
  3. ↑ 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.
  4. ↑ 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.
  5. ↑ Stadlbauer, W.; Kappe, T. (1999). "The Chemistry of Carbon Subsulfide". Sulfur Reports. 21 (4): 423–445. doi:10.1080/01961779908047951.
  6. ↑ 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.
This page is based on this Wikipedia article
Text is available under the CC BY-SA 4.0 license; additional terms may apply.
Images, videos and audio are available under their respective licenses.