Potentiometric studies on the protonation constants and solvation of some$alpha$-amino acid benzyl-and t-butyl-esters in ethanol-water mixtures

Abstract

To gain more information about the effect of solvent on a-amino acid benzyl- and t-butyl- esters, the stoichiometric protonation constants of 10 esters (glycine benzyl ester, L-alanine benzyl ester, L-valine benzyl ester, L-serine benzyl ester, glycine t-butyl ester, L-alanine t-butyl ester, L-valine t-butyl ester, L-leucine t-butyl ester, L-phenylalanine t-butyl ester and L-isoleucine t-butyl ester) in 20%-80% (v/v) ethanol-water mixtures were determined at an ionic strength of 0.10 M NaCl and at 25.0 ± 0.1 °C under nitrogen atmosphere. A potentiometric method was used and the calculation of constants was carried out using the PKAS computer program. The logarithm of the protonation constants of the above-mentioned a-amino acid esters linearly decreased with increases in ethanol contents but the values that determined 80% ethanol did not follow this linear trend. The variation of these constants is discussed on the basis of specific solute-solvent interactions.