{{Chembox | ImageFileL1 = Thioformaldehyde-2D.png | ImageSizeL1 = | ImageAltL1 = Structural formula of thioformaldehyde | ImageClassL1 = skin-invert | ImageFileR1 = Thioformaldehyde-3D-vdW.png | ImageSizeR1 = | ImageAltR1 = Ball-and-stick model of the thioformaldehyde molecule | ImageClassR1 = bg-transparent | IUPACName = Thioformaldehyde | OtherNames = | SystematicName = Methanethial | Section1 = {{Chembox Identifiers | CASNo = 865-36-1 | EINECS = 200-454-1 | PubChem = 79115 | ChemSpiderID = 71446 | SMILES = C=S | StdInChI = 1S/CH2S/c1-2/h1H2 | StdInChIKey = DBTDEFJAFBUGPP-UHFFFAOYSA-N }} | Section2 = {{Chembox Properties |C=1|H=2|S=1 | Appearance = unknown | Density = | MeltingPt = | BoilingPt = | Solubility = }} | Section3 = {{Chembox Hazards | MainHazards = | FlashPt = | AutoignitionPt = }} }} '''Thioformaldehyde''' is the organosulfur compound with the formula CH<sub>2</sub>S. 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.<ref>{{cite journal |doi=10.1016/0022-2852(71)90284-0 |title=Microwave spectrum, ground state structure, and dipole moment of thioformaldehyde |date=1971 |last1=Johnson |first1=Donald R. |last2=Powell |first2=Francis X. |last3=Kirchhoff |first3=William H. |journal=Journal of Molecular Spectroscopy |volume=39 |pages=136–145 |bibcode=1971JMoSp..39..136J }}</ref> The molecule has been observed in the interstellar medium<ref>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.</ref> and has attracted much attention for its fundamental nature.<ref>{{cite journal|doi=10.1146/annurev.pc.34.100183.000335|title=The Spectroscopy of Formaldehyde and Thioformaldehyde|year=1983|last1=Clouthier|first1=D. J.|last2=Ramsay|first2=D. A.|journal=Annual Review of Physical Chemistry|volume=34|pages=31–58|bibcode=1983ARPC...34...31C}}</ref> 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(SCH<sub>2</sub>)(CO)<sub>2</sub>(PPh<sub>3</sub>)<sub>2</sub>.<ref>{{cite journal |doi=10.1039/C0DT00975J|title=The coordination chemistry of small sulfur-containing molecules: A personal perspective|year=2011|last1=Schenk|first1=Wolfdieter A.|journal=Dalton Trans|volume=40|issue=6|pages=1209–1219|pmid=21088787}}</ref> thumb|center|Synthesis of a tungsten thioformaldehyde complex. thumb|center|Synthesis of an osmium thioformaldehyde complex. ==References== <references />
{{Molecules detected in outer space}}
Category:Thioaldehydes