A new strategy to generate super and hyper acids with simple organic molecules exploiting σ-hole interaction†
Super and hyper acidity can be achieved using σ-hole non-covalent interactions with simple organic systems. The σ-hole interaction can stabilize the conjugate base of acids to such an extent that cyclopentadiene yields a ΔHacid of 256 kcal mol−1, which is ∼100 kcal mol−1 lower than the reported results. The hyper acidic value of 209.0 kcal mol−1 of organic acids has been achieved without electron-withdrawing substituents rather exploiting only σ-hole interaction. Remarkably, the 1st and 2nd acidity values (∼229 kcal mol−1) of comparable strength in the hyperacid range have been observed for the first time using DFT computations. The simple organic acids were predicted to reach the pKa values in the range of −7.3 to −7.8 in DMSO, which is remarkably lower than previous reports. These stable anions can be a potential candidate for application as an effective electrolyte in lithium-ion batteries.