Thioformaldehyde

Thioformaldehyde
Structural formula of thioformaldehyde	Ball-and-stick model of the thioformaldehyde molecule
Names
	Other names methanethial
Identifiers
CAS Number	865-36-1;
3D model (JSmol)	Interactive image;
ChemSpider	71446;
EC Number	200-454-1;
PubChem CID	79115;
CompTox Dashboard (EPA)	DTXSID70952941 ;
	InChI InChI=1S/CH2S/c1-2/h1H2 Key: DBTDEFJAFBUGPP-UHFFFAOYSA-N;
	SMILES C=S;
Properties
Chemical formula	CH2S
Molar mass	46.09
Appearance	unknown
	Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
	Infobox references

Thioformaldehyde is the organosulfur compound with the formula CH₂S. This compound is very rarely observed because it oligomerizes to 1,3,5-trithiane, which is a stable colorless compound with the same empirical formula. Despite its instability under normal terrestrial conditions, the molecule has been observed in the interstellar medium[1] and has attracted much attention for its fundamental nature.[2] The tendency of thioformaldehyde to form chains and rings is a manifestation of the double bond rule.

Although thioformaldehyde tends to oligomerize, many metal complexes are known. One example is Os(SCH₂)(CO)₂(PPh₃)₂.[3]

Synthesis of a tungsten thioformaldehyde complex.

Synthesis of a osmium thioformaldehyde complex.

References

Despois, D., "Radio Line Observations of Molecular and Isotopic Species in Comet C/1995 O1 (Hale-Bopp) Implications on the Interstellar Origin of Cometary Ices", Earth, Moon, Planets 1999, 79, 103-124.
Clouthier, D. J.; Ramsay, D. A. (1983). "The Spectroscopy of Formaldehyde and Thioformaldehyde". Annual Review of Physical Chemistry. 34: 31–58. Bibcode:1983ARPC...34...31C. doi:10.1146/annurev.pc.34.100183.000335.
Schenk, Wolfdieter A. (2011). "The coordination chemistry of small sulfur-containing molecules: A personal perspective". Dalton Trans. 40 (6): 1209–1219. doi:10.1039/C0DT00975J. PMID 21088787.

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[1] Despois, D., "Radio Line Observations of Molecular and Isotopic Species in Comet C/1995 O1 (Hale-Bopp) Implications on the Interstellar Origin of Cometary Ices", Earth, Moon, Planets 1999, 79, 103-124.

[2] Clouthier, D. J.; Ramsay, D. A. (1983). "The Spectroscopy of Formaldehyde and Thioformaldehyde". Annual Review of Physical Chemistry. 34: 31–58. Bibcode:1983ARPC...34...31C. doi:10.1146/annurev.pc.34.100183.000335.

[3] Schenk, Wolfdieter A. (2011). "The coordination chemistry of small sulfur-containing molecules: A personal perspective". Dalton Trans. 40 (6): 1209–1219. doi:10.1039/C0DT00975J. PMID 21088787.