Methylene


Methylene
Methylene
Identifiers
CAS number 2465-56-7
PubChem 123164
ChemSpider 109779 YesY
MeSH carbene
ChEBI CHEBI:29357 YesY
Beilstein Reference 1696832
Gmelin Reference 56
Jmol-3D images Image 1
Properties
Molecular formula CH22•
Molar mass 14.0266 g mol-1
Exact mass 14.015650064 g mol-1
Appearance Colourless gas
Solubility in water Reacts
Thermochemistry
Std enthalpy of
formation
ΔfHo298
386.39 kJ mol-1
Standard molar
entropy
So298
193.93 J K-1 mol-1
Except where noted otherwise, data are given for materials in their standard state (at 25 °C, 100 kPa)
Infobox references

Methylene is a carbene encountered in organic chemistry.[2][3] Methylene has a non-linear triplet ground state and is thus paramagnetic. It is stable in the gaseous state. Methylene can be considered to be a diradical; addition reactions are very fast and exothermic. Methylene tends to dimerize at high concentrations into ethene.[4]

Trivia

Carl Barks was the first to make a reference to methylene in his comic Donald Duck, almost 20 years before science could prove its existence.[5]

References

  1. ^ a b "methanediyl (CHEBI:29357)". Chemical Entities of Biological Interest (ChEBI). UK: European Bioinformatics Institute. IUPAC Name. https://www.ebi.ac.uk/chebi/searchId.do?chebiId=CHEBI%3A29357. 
  2. ^ Hoffmann, Roald (2005). Molecular Orbitals of Transition Metal Complexes. Oxford. p. 7. ISBN 0198530935 
  3. ^ IUPAC, Compendium of Chemical Terminology, 2nd ed. (the "Gold Book") (1997). Online corrected version:  (2006–) "carbenes".
  4. ^ Lazár, Milan; Lazr̀, Milan (1989). Free radicals in chemistry and biology. Boca Raton: CRC Press. ISBN 0-8493-5387-4. 
  5. ^ http://www.cracked.com/article_19021_5-amazing-things-invented-by-donald-duck-seriously_p2.html


Further reading

  • Shavitt, I (1985). "Geometry and singlet-triplet energy gap in methylene: A critical review of experimental and theoretical determinations". Tetrahedron 41 (8): 1531. doi:10.1016/S0040-4020(01)96393-8.