Titrations in Non-Aqueous Solvents: The Relative Strengths of Acids

Abstract

VI. SUMMARY At this point in time several major problems must be solved before the results of acid-base reactions can be predicted, even moderately well in given solvent. Theoretically, it would be desireable to be able to estimate, on the basis of energy, the intrinsic acidity of acids as well as the basicity of substances with which acids react under practical circumstances, whether the latter is a solvent or a reference base. The available data suggest that hydrogen-containing substances exhibit characteristic protonic acidities which can be manifested, more or less, in different solvents. The ionization of a substance to form protons in the gas phase is a suggested unambiguous measure of its inherent acid strength, but sufficient thermochemical data are not available to estimate the extents of such processes for a series of related compounds. The gas phase ionization can be related to the ionization process in solution by considering the solvation of the molecular form of the acid, its conjugate base,...