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In [[chemistry]], a '''carbene''' is a [[molecule]] containing a neutral [[carbon]] atom with a [[Valence (chemistry)|valence]] of two and two unshared [[valence electron]]s. The general formula is R-(C''':''')-R' or R=C''':''' where the R represent [[substituent]]s or hydrogen atoms.
The term "carbene" may also refer to the specific compound H<sub>2</sub>C''':''', also called [[methylene radical|methylene]], the parent [[hydride]] from which all other carbene compounds are formally derived.<ref>{{Cite book|title=Molecular Orbitals of Transition Metal Complexes|isbn=978-0-19-853093-0|page=7|last=Hoffmann|first=Roald|author-link=Roald Hoffmann|publisher=Oxford|year=2005}}</ref><ref>{{GoldBookRef|title=carbenes|file=C00806}}</ref> Carbenes are classified as either [[singlet state|singlets]] or [[triplet state|triplets]], depending upon their electronic structure. Most carbenes are very short lived, although [[persistent carbene]]s <ref>For detailed reviews on stable carbenes, see: (a) {{cite journal | last1 = Bourissou | first1 = D. | last2 = Guerret | first2 = O. | last3 = Gabbai | first3 = F. P. | last4 = Bertrand | first4 = G. | year = 2000 | title = Stable Carbenes| journal = [[Chem. Rev.]] | volume = 100 | issue = 1 | pages = 39–91 | doi = 10.1021/cr940472u | pmid = 11749234 }} (b) {{cite journal | last1 = Melaimi | first1 = M. | last2 = Soleilhavoup | first2 = M. | last3 = Bertrand | first3 = G. | title = Stable cyclic carbenes and related species beyond diaminocarbenes | year = 2010 | journal = [[Angew. Chem. Int. Ed.]] | volume = 49 | issue = 47 | pages = 8810–8849 | doi = 10.1002/anie.201000165 | pmid = 20836099 | pmc = 3130005 }}</ref> are known.
==Structures and bonding==
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