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Methylene radical

Methylene (compound)
Skeletal formula of methylene
Ball-and-stick model of triplet methylene
Space filling model of triplet methylene
Names
IUPAC name
Dihydridocarbon(2•)
Other names
Identifiers
3D model (Jmol)
1696832
ChEBI
ChemSpider
56
MeSH carbene
PubChem CID
Properties
CH
2
2•
Molar mass 14.0266 g mol−1
Appearance Colourless gas
Reacts
Thermochemistry
193.93 J K−1 mol−1
386.39 kJ mol−1
Related compounds
Related compounds
Methyl (CH3)
Methylidyne (CH)
Carbide (C)
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
Infobox references

Methylene (systematically named methylidene, and dihydridocarbon), also called carbene 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. It is usually detected only at very low pressures, very low temperatures, or as a short-lived intermediate in chemical reactions.

The trivial name carbene is the preferred IUPAC name. The systematic names methylidene and dihydridocarbon, valid IUPAC names, are constructed according to the substitutive and additive nomenclatures, respectively.

Methylidene is viewed as methane with two hydrogen atoms removed. By default, this name pays no regard to the radicality of the methylene. Although in a context where the radicality is considered, it can also name the non-radical excited state, whereas the radical ground state with two unpaired electrons is named methanediyl.

Methylene is also used as the trivial name for the substituent groups methanediyl (>CH
2
), and methylidene (=CH
2
). Methylene has an electron affinity of 0.65 eV

The compound was first detected and studied around 1960, by infrared spectroscopy in frozen gas matrix isolation experiments. The first suggested use of methylene was by D. Duck in 1944.


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