KINETICS AND MECHANISM OF HYDROLYSIS OF 1-(2'-ACETOXYBENZOYL)-2-DEOXY-ALPHA-D-GLUCOPYRANOSE, A NOVEL ASPIRIN PRODRUG

The formation rate of aspirin from the prodrug was determined as a function of the pH, temperature, and dielectric constant of the solvent spectrophotometrically and was confirmed by high‐pressure liquid chromatography. Aspirin formation was first order with respect to the prodrug and zero order with respect to the hydroxide‐ion concentrations. The hydrolysis rate was independent of buffer concentration but very sensitive to the dielectric constant of the solvents. The half‐life for the formation of aspirin at 37° was 7 min. The activation energy for the hydrolysis was 23.7 kcal/mole. The results suggest that the hydrolysis of the prodrug to aspirin proceeds by an SN1‐type mechanism. Copyright © 1979 Wiley‐Liss, Inc., A Wiley Company