The nature of bonding in the 2-norbornyl cation was the center of a vigorous, well-known debate in the chemistry community through the middle of the twentieth century. While the majority of chemists believed that a three-center two-electron bond best depicted its ground state electronic structure, others argued that all data concerning the 2-norbornyl cation could be explained by depicting it as a rapidly equilibrating pair of cations.
At the height of the debate, all chemists agreed that the delocalized picture of electron bonding could be applied to the 2-norbornyl cation. But this did not answer the fundamental question on which the debate hinged. Researchers continued to search for novel ways to determine whether the three-centered delocalized picture described a low-energy transition state (saddle point on the multidimensional potential energy surface) or a potential energy minimum in its own right. Proponents of the "classical" picture believed that the system was best described by a double-well potential with a very low barrier, while those in the "non-classical" camp envisioned the delocalized electronic state to describe a single potential energy well.