Methylene (compound)

Methylene
Skeletal formula of methylene
Ball-and-stick model of triplet methylene
Ball-and-stick model of triplet methylene
Space filling model of triplet methylene
Space filling model of triplet methylene
Names
IUPAC name
Dihydridocarbon(2•)[1]
Preferred IUPAC name
Methylidene[2]
Other names
Dihydridocarbon
Carbene
Methylene
Methene[1]
Identifiers
3D model (JSmol)
1696832
ChEBI
ChemSpider
56
MeSH carbene
  • InChI=1S/CH2/h1H2 checkY
    Key: HZVOZRGWRWCICA-UHFFFAOYSA-N checkY
  • [CH2]
Properties
CH
2
2•
Molar mass 14.0266 g mol−1
Appearance Colourless gas
Reacts
Conjugate acid Methenium
Thermochemistry
193.93 J K−1 mol−1
386.39 kJ mol−1
Related compounds
Related compounds
Methyl (CH3)
Methylidyne (CH)
Carbide (C)
Silylene (SiH2)
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).

Methylene (IUPAC name: Methylidene, also called carbene or methene) is an organic compound with the chemical formula CH
2
(also written [CH
2
]
). It is a colourless gas that fluoresces in the mid-infrared range, and only persists in dilution, or as an adduct.

Methylene is the simplest carbene.[3]: p.7 [4] It is usually detected only at very low temperatures, or as a short-lived intermediate in chemical reactions.[5]

  1. ^ a b "methanediyl (CHEBI:29357)". Chemical Entities of Biological Interest. UK: European Bioinformatics Institute. 14 January 2009. IUPAC Names. Retrieved 2 January 2012.
  2. ^ Henri A. Favre; Warren H. Powell (2014). Nomenclature of Organic Chemistry : IUPAC Recommendations and Preferred Names 2013. Cambridge, England: Royal Society of Chemistry. p. 1054. ISBN 978-0-85404-182-4.
  3. ^ Roald Hoffman (2005), Molecular Orbitals of Transition Metal Complexes. Oxford. ISBN 0-19-853093-5
  4. ^ IUPAC, Compendium of Chemical Terminology, 2nd ed. (the "Gold Book") (1997). Online corrected version: (2006–) "carbenes". doi:10.1351/goldbook.C00806
  5. ^ W. B. DeMore and S. W. Benson (1964), Preparation, properties, and reactivity of methylene. In Advances in Photochemistry, John Wiley & Sons, 453 pages. ISBN 0470133597