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Thioformaldehyde

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From Wikipedia, the free encyclopedia

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

Properties

Chemical formula

CH₂S

Molar mass

46.09

Appearance

unknown

Except where otherwise noted, data are given for materials in theirstandard state (at 25 °C [77 °F], 100 kPa).

Infobox references

Chemical compound

Thioformaldehyde is theorganosulfur compound with the formula CH₂S. It is the simplestthioaldehyde. This compound is not observed in the condensed state (solid or liquid) because itoligomerizes to1,3,5-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 ofdimethyl disulfide.^[1] The molecule has been observed in theinterstellar 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 thedouble 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 an osmium thioformaldehyde complex.

References

[edit]

^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 Imidogen Iron(II) oxide Magnesium monohydride Methylidyne radical Nitric oxide Nitrogen (molecular) Oxygen (molecular) Phosphorus monoxide Phosphorus mononitride Potassium chloride Silicon carbide Silicon monoxide Silicon monosulfide Sodium chloride Sodium iodide Sulfanyl Sulfur mononitride 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 Methylidynephosphane N₂H⁺ Nitrous oxide Nitroxyl Ozone Potassium cyanide Sodium cyanide Sodium hydroxide Silicon carbonitride c-Silicon dicarbide SiNC Sulfur dioxide Thioformyl Thioxoethenylidene Titanium dioxide Tricarbon Trihydrogen cation Water
Four atoms	Acetylene Ammonia Cyanoethynyl Formaldehyde Fulminic acid HCCN Hydrogen peroxide Hydromagnesium isocyanide Isocyanic acid Isothiocyanic acid Ketenyl Methyl cation Methyl radical Methylene amidogen Propynylidyne Protonated carbon dioxide Protonated hydrogen cyanide Silicon tricarbide Thiocyanic acid Thioformaldehyde Tricarbon monosulfide Tricarbon monoxide
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 Cyclopropenone Diacetylene E-Cyanomethanimine Ethylene Formamide HC₄N Ketenimine Methanethiol Methanol Methyl isocyanide Pentynylidyne Propynal Protonated cyanoacetylene
Seven atoms	Acetaldehyde Acrylonitrile Vinyl cyanide Cyanodiacetylene Ethylene oxide Glycolonitrile Hexatriynyl radical Methyl isocyanate Methylamine Propyne Vinyl alcohol
Eight atoms	Acetic acid Acrolein Aminoacetonitrile Cyanoallene Ethanimine Glycolaldehyde Hexapentaenylidene Methyl formate Methylcyanoacetylene
Nine atoms	Acetamide Cyanohexatriyne Dimethyl ether Ethanethiol Ethanol Methyldiacetylene N-Methylformamide Octatetraynyl radical Propene Propionitrile
Ten atoms or more	Acetone Benzene Benzonitrile Buckminsterfullerene (C₆₀, C₆₀⁺, fullerene, buckyball) Butyronitrile C₇₀ fullerene Cyanodecapentayne Ethyl formate Ethylene glycol Heptatrienyl radical Methyl acetate Methyl-cyano-diacetylene Methyltriacetylene Propionaldehyde Pyrimidine

Deuterated
molecules

Unconfirmed

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Category:

Thioaldehydes

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