Decomposition and Stabilization of Drugs. XI. Structure and Stability of Aminoalkylesters. (3)

Abstract

In order to examine the structure and stability relationship of secondary amine of aminoalkylesters, derivatives of [(C₆H₅)(m-CH₃O-C₆H₄) CHCOOCH₂CH₂NHR³] were synthesized, changing R³ to CH₃ (I), C₂H₅ (II), n-C₃H₇ (III), iso-C₃H₇ (IV), n-C₄H₉ (V) and CH₂C₆H₅ (VII). With the use of a protonated amine ester as a reaction species, catalytic constants of hydrogen ion (k_H) and hydroxyl ion (k_OH) were determined. The substituent effect on k_H and k_OH was explained with Taft Es values, and the case in which an unprotonated amine ester was taken as being hydrolyzed spontaneously was discussed briefly.