Crystal structure closes classic carbocation case

 

norbornyl classical structure
Herb Brown favoured rapidly equilibrating classical enantiomers of the 2-norbornyl cation
norbornyl cation nonclassical structureWinstein proposed the nonclassical structure of the 2-norbornyl cation, now shown to be correct

F Scholz et al, Science, 2013, DOI: 10.1126/science.1238849

After more than 60 years, crystals of the 2-norbornyl cation have finally put its ‘nonclassical’ structure, with a pentacoordinate carbon, beyond doubt
German scientists have solved the long-sought crystal structure of an ion at the frontline of a war of interpretation that raged for years. Karsten Meyer from Friedrich-Alexander-University in Erlangen and his teammates have ended a 64 year wait for this most definitive evidence of ‘nonclassical’ 2-norbornyl carbocation structures. ‘The crystallography was a tour-de-force,’ Meyer tells Chemistry World. ‘The procedure is insane – it put us through torture.
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