text: Advocates of the non-classical nature of the stable 2-norbornyl cation typically depict the species using either resonance structures or a single structure with partial bonds (see Figure 2). This hypovalent interaction can be imagined as the net effect of i) a partial sigma bond between carbons 1 and 6, ii) a partial sigma bond between carbons 2 and 6, and iii) a partial pi bond between carbons 1 and 2. Each partial bond is represented as a full bond in one of the three resonance structures or as a dashed partial bond if the cation is depicted through a single structure.
  There has been some debate over how much the pi-bonded resonance structure actually contributes to the delocalized electronic structure. Through H and C NMR spectroscopy, it has been confirmed that significant positive charge lies on methylene carbon 6. This is surprising as primary carbocations are much less stable than secondary carbocations. However, the 2-norbornyl cation can be formed from derivatives of β-(Δ-cyclopentenyl)-ethane, indicating that the pi-bonded resonance structure is significant.
  The 2-norbornyl cation was one of the first examples of a non-classical ion. Non-classical ions can be defined as organic cations in which electron density of a filled bonding orbital is shared over three or more centers and contains some sigma-bond character. The 2-norbornyl cation is seen as the prototype for non-classical ions. Other simple cations such as protonated acetylene (ethynium, ), protonated ethylene (ethenium, ), and protonated ethane (ethanium, ) have been shown to be best described as non-classical through infrared spectroscopy.
  The most frequently proposed molecular orbital depiction of the 2-norbornyl cation is shown in Figure 3. Two p-type orbitals, one on each of carbons 1 and 2, interact with a sp-hybridized orbital on carbon 6 to form the hypovalent bond. Extended Hückel Theory calculations for the 2-norbornyl cation suggest that the orbital on carbon 6 could instead be sp-hybridized, though this only affects the geometry of the geminal hydrogens.