Therefore, a double bond between C1 and C7 is likely to break to a diradical. Similarly, a double bond on one-carbon bridges of bicyclo [2.1.1] hexane and bicyclo [1.1.1] pentane are even more difficult to form because pyramidalization in smaller bicyclo olefins is more pronounced. Our CASPT2 computations suggest that in a hypothetical bicyclo[2.2.1]hept-4(7)-ene, or as conventionally known, 7-norbornene, the triplet diradical remains 16 kcal.mol -1 lower in energy than the singlet as a double bond between C1 and C7 is too weak to stabilize the associated singlet state, Figure . However, one can deliberately take advantage of the orthogonality of atomic p-orbitals and pyramidalization of C1 in norbornane structure to stabilize a carbanion on C1 while stabilizing a carbocation on C7 that can easily planarize instead of the usual diradical formation scenario. To achieve this goal, one must break the near-degeneracy of the highest occupied molecular orbitals (HOMOs) in the triplet diradical state. The orbitals accommodating such ion-pair do not overlap with each other and the neighboring carbons merely benefit from electrostatic stabilization of two adjacent ions, formally accommodated in carbon's atomic p-orbitals. In the following, utilizing this strategy, we introduce a series of novel hydrocarbons with ionic p-bonds in which anion and cation are separated by the distortion of the σ-framework.