Carbon subsulfide: Difference between revisions

{{Short description|1=Organic compound with the structure S=C=C=C=S}}

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|Watchedfields = changed

|verifiedrevid = 445987302

|ImageFile =Carbon subsulfide.svg

|ImageAlt = Full structural formula of carbon subsulfide

|ImageFile1 = Carbon subsulfide 3D spacefill.png

|ImageAlt1 = Space-filling model of the carbon subsulfide molecule

|PIN = Propa-1,2-diene-1,3-dithione

|OtherNames = Carbon Subsulfide, Tricarbon Disulfide

|Section1={{Chembox Identifiers

|CASNo_Ref = {{cascite|correct|??}}

|CASNo = 627-34-9

|PubChem = 11062317

|ChemSpiderID_Ref = {{chemspidercite|changed|chemspider}}

|ChemSpiderID = 9237470

|SMILES = S=C=C=C=S

|InChI = 1/C3S2/c4-2-1-3-5

|InChIKey = RMCQREAPGZPWGK-UHFFFAOYAC

|StdInChI_Ref = {{stdinchicite|changed|chemspider}}

|StdInChI = 1S/C3S2/c4-2-1-3-5

|StdInChIKey_Ref = {{stdinchicite|changed|chemspider}}

|StdInChIKey = RMCQREAPGZPWGK-UHFFFAOYSA-N

}}

|Section2={{Chembox Properties

|C=3 | S=2

|Appearance = red liquid

|Density = 1.27 g cm⁻³

|Solubility = insoluble

|MeltingPtC = -1

|BoilingPtC = 90

}}

|Section3={{Chembox Related

|OtherCompounds = [[Carbon suboxide]]<br />[[Carbon disulfide]]<br>[[Ethenedithione]]

}}

'''Carbon subsulfide''' is an [[Organic compound|organic]], [[Organosulfur compounds|sulfur-containing]] chemical compound with the [[Chemical formula|formula]] {{chem2|C3S2}} and [[Structural formula|structure]] {{chem2|S\dC\dC\dC\dS}}. This deep red liquid is [[immiscible]] with water but soluble in [[organic solvent]]s. It readily [[polymerizes]] at room temperature to form a hard black solid.

C₃S₂ was discovered by Béla Lengyel,<ref>{{ cite journal | author = von Lengyel, B. | title = Ueber ein neues Kohlenstoffsulfid | journal = Berichte der Deutschen Chemischen Gesellschaft | year = 1893 | volume = 26 | issue = 3 | pages = 2960–2968 | doi = 10.1002/cber.189302603124 | url = https://zenodo.org/record/1425718 }}</ref> who assigned it an unsymmetrical structure. Later, [[Infrared spectroscopy|infrared]] and [[Raman spectroscopy]] showed that the structure is symmetrical with a D_∞h [[symmetry group|point group symmetry]],<ref>{{ cite journal |author1=Smith, W. H. |author2=Leroi, G. E. | title = Infrared and Raman Spectra of Carbon Subsulfide | journal = The Journal of Chemical Physics | year = 1966 | volume = 45 | issue = 5 | pages = 1778–1783 | doi = 10.1063/1.1727828 |bibcode = 1966JChPh..45.1778S }}</ref> 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&nbsp;°C as well as flash vacuum [[pyrolysis]] (FVP) of 1,2-dithiole-3-thiones.<ref>{{cite journal | author = Pedersen, C. T. | title = The formation of 1,2-propadiene-1,3-dithione (carbon subsulfide) from flash vacuum pyrolysis of 1,2-dithiole-3-thiones | journal = Tetrahedron Letters | year = 1996 | volume = 37 | issue = 27 | pages = 4805–4808 | doi = 10.1016/0040-4039(96)00941-0}}</ref>

Among its few known reactions, C₃S₂ reacts with bromine to form the cyclic disulfide.<ref>{{cite journal |author1=Stadlbauer, W. |author2=Kappe, T. | title = The Chemistry of Carbon Subsulfide | journal = Sulfur Reports | year = 1999 | volume = 21 | issue = 4 | pages = 423–445 | doi = 10.1080/01961779908047951}}</ref>

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

Using microwave spectroscopy, small C_nS₂ clusters have been detected in [[interstellar medium]].<ref>{{cite journal |author1=Cernicharo, J. |author2=Guelin, M. |author3=Hein, H. |author4=Kahane, C. | title = Sulfur in IRC + 10216 | journal = Astronomy and Astrophysics | issn = 0004-6361 | year = 1987 | volume = 181 | issue = 1 | pages = L9–L12 | bibcode = 1987A&A...181L...9C}}</ref> The rotational transitions of these molecular carbon sulfides matched with the corresponding molecules.

{{sulfur compounds}}

{{Carbon compounds}}

[[Category:Organic compounds]]

[[Category:Foul-smelling chemicals]]