text: Radioactive isotope labeling experiments provide a powerful tool for determining the structure of organic molecules. By systematically decomposing the 2-norbornyl cation and analyzing the amount of radioactive isotope in each decomposition product, researchers were able to show further evidence for the non-classical picture of delocalized bonding (see Figure 9). Proponents of the nonclassical picture would expect 50% of the generated CO in the decomposition in Figure 9 to contain C, while proponents of the classical picture would expect more of the generated CO to be radioactive due to the short-lived nature of the cation. 40% of the carbon dioxide produced via decomposition has been observed to be radioactive, suggesting that the non-classical picture is more correct.
  Further distinction between non-classical and classical structures of the 2-norbornyl cation is possible by combining NMR experiments with isotope-labeling experiments. Isotopic substitution of one of two deuterium atoms for a hydrogen atom causes the environment of nearby NMR-active atoms to change dramatically. Asymmetric deuterium isotope labeling (substitution) will cause a set of carbons that were all equivalent in the all-hydrogen species to be split into two or more sets of equivalent carbons in the deutero-labeled species; this will be manifested in the NMR spectrum as one peak in the all-hydrogen species' spectrum becoming at least two "split" peaks in the deutero-labeled species. If a system is undergoing a rapid equilibrium at a rate faster than the timescale of a C NMR experiment, the relevant peak will be split dramatically (on the order of 10-100 ppm). If the system is instead static, the peak will be split very little. The C NMR spectrum of the 2-norbornyl cation at -150 °C shows that the peaks corresponding to carbons 1 and 2 are split by less than 10 ppm (parts per million) when this experiment is carried out, indicating that the system is not undergoing a rapid equilibrium as in the classical picture.