DescriptionClassical versus Non-classical Bonding of the in-Bicyclo(4.4.4)-1-tetradecyl Cation.jpg
English: The classical and non-classical bonding of the in-bicyclo[4.4.4]-1-tetradecyl cation. The non-classical model (a) shows one hydrogen bridged molecule while the classical model (b) would imply rapid interconversion between two distinct carbocations and lack the hydrogen bridge. McMurry confirmed the presence of the 3-center 2-electron bond and the hydrogen bridged species by NMR.
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