Thioformaldehyde

Thioformaldehyde
Names
	IUPAC name Thioformaldehyde
	Systematic IUPAC name 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)	DTXSID901336564 DTXSID70952941, DTXSID901336564 ;
	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. It is the simplest thioaldehyde. This compound is not observed in the condensed state (solid or liquid) because it oligomerizes to 1,3,5-trithiane, which is a stable colorless compound with the same empirical formula.

Despite the instability of these concentrated forms, thioformaldehyde as a dilute gas has been extensively studied. For these purposes, it is produced by thermal decomposition of dimethyl disulfide.^[1] The molecule has been observed in the interstellar medium^[2] and has attracted much attention for its fundamental nature.^[3] 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.^[4]

Synthesis of a tungsten thioformaldehyde complex.

Synthesis of a osmium thioformaldehyde complex.

References

^ Johnson, Donald R.; Powell, Francis X.; Kirchhoff, William H. (1971). "Microwave spectrum, ground state structure, and dipole moment of thioformaldehyde". Journal of Molecular Spectroscopy. 39: 136–145. Bibcode:1971JMoSp..39..136J. doi:10.1016/0022-2852(71)90284-0.
^ 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.

[1] Johnson, Donald R.; Powell, Francis X.; Kirchhoff, William H. (1971). "Microwave spectrum, ground state structure, and dipole moment of thioformaldehyde". Journal of Molecular Spectroscopy. 39: 136–145. Bibcode:1971JMoSp..39..136J. doi:10.1016/0022-2852(71)90284-0.

[2] 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.

[3] 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.

[4] 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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