In organic chemistry, the term 2-norbornyl cation (or 2-bicyclo[2.2.1]heptyl cation) describes one of the three carbocations formed from derivatives of norbornane. Though 1-norbornyl and 7-norbornyl cations have been studied, the most extensive studies and vigorous debates have been centered on the exact structure of the 2-norbornyl cation. The nature of bonding in the 2-norbornyl cation incorporated many new ideas into the field’s understanding of chemical bonds. Similarities can be seen between this cation and others, such as boranes.