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Abstract
Some representative N-aryl-D-pentopyranosylamines have been synthesized and their structures confirmed by 13C NMR. The kinetics of their acid-catalyzed hydrolyses have been studied at various temperatures by UV and HPLC techniques. The influence of the changes in the aglyconic and sugar moieties has been examined. The rates of hydrolyses increased as the pH of the solution decreased and the base strength of the parent amine increased. The lability of the C1N bond increased in the order xyloside < lyxoside < riboside < arabinoside. A bimolecular A-2 mechanism is suggested for the acid-catalyzed hydrolysis of N-aryl-D-pentopyranosylamines. involving the formation of a Schiff base intermediate.