Thioformaldehyde

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. The molecule has been observed in the interstellar medium and has attracted much attention for its fundamental nature. 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.

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.

Molecules detected in outer space

Molecules

Diatomic	Aluminium monochloride Aluminium monofluoride Aluminium(II) oxide Argonium Carbon cation Carbon monophosphide Carbon monosulfide Carbon monoxide Cyano radical Diatomic carbon Fluoromethylidynium Helium hydride ion Hydrogen chloride Hydrogen fluoride Hydrogen (molecular) Hydroxyl radical Iron(II) oxide Magnesium monohydride Methylidyne radical Nitric oxide Nitrogen (molecular) Imidogen Sulfur mononitride Oxygen (molecular) Phosphorus monoxide Phosphorus mononitride Potassium chloride Silicon carbide Silicon monoxide Silicon monosulfide Sodium chloride Sodium iodide Sulfanyl Sulfur monoxide Titanium(II) oxide
Triatomic	Aluminium(I) hydroxide Aluminium isocyanide Amino radical Carbon dioxide Carbonyl sulfide CCP radical Chloronium Diazenylium Dicarbon monoxide Disilicon carbide Ethynyl radical Formyl radical Hydrogen cyanide (HCN) Hydrogen isocyanide (HNC) Hydrogen sulfide Hydroperoxyl Iron cyanide Isoformyl Magnesium cyanide Magnesium isocyanide Methylene N₂H Nitrous oxide Nitroxyl Ozone Methylidynephosphane Potassium cyanide Trihydrogen cation Sodium cyanide Sodium hydroxide Silicon carbonitride c-Silicon dicarbide SiNC Sulfur dioxide Thioformyl Thioxoethenylidene Titanium dioxide Tricarbon Water
Four atoms	Acetylene Ammonia Isocyanic acid Cyanoethynyl Formaldehyde Fulminic acid HCCN Hydrogen peroxide Hydromagnesium isocyanide Isocyanic acid Isothiocyanic acid Ketenyl Methylene amidogen Methyl cation Methyl radical Propynylidyne Protonated carbon dioxide Protonated hydrogen cyanide Silicon tricarbide Thioformaldehyde Tricarbon monoxide Tricarbon monosulfide Thiocyanic acid
Five atoms	Ammonium ion Butadiynyl Carbodiimide Cyanamide Cyanoacetylene Cyanoformaldehyde Cyanomethyl Cyclopropenylidene Formic acid Isocyanoacetylene Ketene Methane Methoxy radical Methylenimine Propadienylidene Protonated formaldehyde Silane Silicon-carbide cluster
Six atoms	Acetonitrile Cyanobutadiynyl radical E-Cyanomethanimine Cyclopropenone Diacetylene Ethylene Formamide HC₄N Ketenimine Methanethiol Methanol Methyl isocyanide Pentynylidyne Propynal Protonated cyanoacetylene
Seven atoms	Acetaldehyde Acrylonitrile Vinyl cyanide Cyanodiacetylene Ethylene oxide Glycolonitrile Hexatriynyl radical Propyne Methylamine Methyl isocyanate Vinyl alcohol
Eight atoms	Acetic acid Aminoacetonitrile Cyanoallene Ethanimine Glycolaldehyde Hexapentaenylidene Methylcyanoacetylene Methyl formate Acrolein
Nine atoms	Acetamide Cyanohexatriyne Dimethyl ether Ethanol Methyldiacetylene Octatetraynyl radical Propene Ethanethiol Propionitrile N-Methylformamide
Ten atoms or more	Acetone Benzene Benzonitrile Buckminsterfullerene (C₆₀, C₆₀, fullerene, buckyball) C₇₀ fullerene Cyanodecapentayne Ethylene glycol Ethyl formate Methyl acetate Methyl-cyano-diacetylene Methyltriacetylene Propionaldehyde Butyronitrile Pyrimidine Heptatrienyl radical

Deuterated
molecules

Unconfirmed

Category:

Thioaldehydes