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 \alpha -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 \pm 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 \alpha -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.

Keywords: Potentiometry; protonation constants, solvent effect, amino acid esters

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