Editing Carbanion (section)

==History==
A carbanionic structure first made an appearance in the reaction mechanism for the [[benzoin condensation]] as correctly proposed by Clarke and [[Arthur Lapworth]] in 1907.<ref>{{Cite journal| doi = 10.1039/CT9079100694| title = LXV. An extension of the benzoin synthesis| year = 1907| last1 = Clarke | first1 = R. W. L.| last2 = Lapworth | first2 = A.| journal = Journal of the Chemical Society, Transactions| volume = 91| pages = 694–705| url = https://zenodo.org/record/1429713}}</ref> In 1904 [[Wilhelm Schlenk]] prepared {{chem2|[Ph3C]−[NMe4]+}} in a quest for tetramethylammonium (from [[tetramethylammonium chloride]] and 
[[Organosodium chemistry|{{chem2|Ph3CNa}}]])<ref name=":1">{{Cite journal| doi = 10.1002/jlac.19103720102| title = Ueber Triphenylmethyl und Analoga des Triphenylmethyls in der Biphenylreihe|trans-title=On triphenylmethyl and analogues of triphenylmethyl in the biphenyl series| year = 1910| last1 = Schlenk | first1 = W.| last2 = Weickel | first2 = T.| last3 = Herzenstein | first3 = A.| journal = Justus Liebig's Annalen der Chemie| volume = 372| pages = 1–20| url = https://zenodo.org/record/1427585}}</ref> and in 1914 he demonstrated how triarylmethyl radicals could be reduced to carbanions by alkali metals <ref>{{Cite journal| doi = 10.1002/cber.19140470256| title = Über Metalladditionen an freie organische Radikale. XII. Über Triarylmethyle |trans-title=On metal addition to free organic radicals. XII. Tryarylmethyls| year = 1914| last1 = Schlenk | first1 = W.| last2 = Marcus | first2 = E.| journal = Berichte der Deutschen Chemischen Gesellschaft| volume = 47| issue = 2| pages = 1664| url = https://zenodo.org/record/1426557}}</ref> The phrase carbanion was introduced by Wallis and Adams in 1933 as the negatively charged counterpart of the [[carbonium ion]]<ref>{{Cite journal| doi = 10.1021/ja01336a068| year = 1933| last1 = Wallis | first1 = E. S.| title = The Spatial Configuration of the Valences in Tricovalent Carbon Compounds1| last2 = Adams | first2 = F. H.| journal = Journal of the American Chemical Society| volume = 55| issue = 9| pages = 3838}}</ref><ref>{{Cite journal| doi = 10.1351/pac199769020211| title = The first century of physical organic chemistry: A prologue| year = 1997| last1 = Tidwell | first1 = T. T.| journal = Pure and Applied Chemistry| volume = 69| issue = 2| pages = 211–214| s2cid = 98171271| doi-access = free}}</ref>