Water-Catalyzed Amide Hydrolysis in Dilute Aqueous Carbohydrate Solutions

Article abstract of DOI:10.1021/jo00390a035

Rates and thermodynamics activation parameters were determined for the water-catalyzed hydrolysis of the activated amide bond in three 1-acyl-1,2,4-triazoles of different hydrophobicity by using dilute aqueous solutions of simple carbohydrates as the reaction medium.The solutions show thermodynamically almost ideal behavior.It appears that the kinetic medium effects, and, in particular, the changes in Δ^<*>S^<*>. are largely determined by carbohydrate-induced alterations in the three-dimensional hydrogen-bond network of water.The specific, hydration model for carbohydrates, developed by Franks and his associates, appears to provide a key to the understanding of the carbohydrate medium effects on the hydrolytic model reaction