Studies on the Hydrolysis of Glucuronosides. III : The Alkaline Hydrolysis of β-D-Glucopyranosiduronic Acids

Effect of the electron affinity of the aglycone group in the alkaline hydrolysis rate of alkyl- and aryl-β-D-glucopyranosiduronic acid was examined. Electron-attracting aglycone increased the hydrolysis rate of the acid while the electron-releasing aglycone decreased this rate. This relationship is the reverse of the same effect in acid hydrolysis. Hammett value in the rate of alkaline hydrolysis of aryl-βD-glucopyranosiduronic acid was about 1.5 in either N, 2N, or 4N sodium hydroxide at 100°.