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The Transition (vs ΔpKa) from Triple Ions to Free Cations in Poor Protic Ionic Liquids Made from Weak Acids

In mixtures of amines with carboxylic acids, the limited ionicity at 1:1 stoichiometric mixtures is due to insufficient ionization or ion pairing in low-dielectric environments. Higher conductivities have historically been seen at roughly 4:1 acid/base mixing ratios, where simulations have revealed large (and thus more stable) ions: homoassociated anions (AH)(AH)(A−)(HA)(HA) and cationic triple ions (BH+)(AH)(A−)(HA)(HB+). Recent work in understanding the Gibbs energies for degree-of-ionization equilibria hints that there may be an onset, for systems with an acid-base pKa difference increasing towards 10, for the formation of free (unpaired) protonate-amine cations BH+. The transition with increasing ΔpKa is explored in this work, to aid in the prediction of ionicity and conductivity of protic ionic liquids.