Salt effects on the protonation of imidazole in aqueous solution at different ionic strengths: A tentative explanation by a complex formation model

Abstract

Imidazole protonation constants were determined potentiometrically, using a (H+)-glass electrode, in LiCl, NaCl, KCl, CaCl2, MgCl2, tetramethylammonium (Me4N-) iodide and chloride, Et4N-, Pr4N- and Bu4N-iodides. Salt effects were tentatively explained by assuming that complexes [H(Im)X]o (Im = imidazole, X−=Cl− or I−), [M(Im)]2+ (M2+=Mg2+ or Ca2+) and [A(Im)]+ (A+ = tetraalkylammonium cation) were formed in solution. Calcium(II)-selective electrode measurements confirmed our hypothesis about the formation of the Ca2+-imidazole complex. The reliability of the complex formation model is discussed on the basis of its self consistency and in light of previous results.