Starting with bicyclo [2.2.1] heptane (norbornane), we explored two factors: (1) electronic effect of substituents on the stability of the ion pair and (2) the distortion of the σ-framework by extending our quest for stable ionic p-bonds in bicyclo [2.1.1] hexane and bicyclo [1.1.1] pentane structures. To verify the ionic p-bonding in the selected systems, we examined the relative energies of the singlet and triplet states of the molecules, geometric parameters, atomic charges, and the electronic structure of the molecules. An olefin with ionic p-bonding should have a singlet state that is lower than the triplet (biradical) state and a planar C7 structure in its singlet state to prevent any efficient overlap between C1 and C7. Selected species are listed in Figure . Table lists singlet-triplet gaps of the molecules as well as natural atomic charges of anionic and cationic centers computed at ω-B97XD /def2-TZVP level in DMF as solvent using SMD model.