Acidity effect on the cleavage of ether function intramolecularly assisted by the amide group. Part 5

The rate dependence on both the acidity and the temperature of the hydrolysis of N-(methoxyprop-2-yl)benzanilide (1), assisted by vicinal amide function, was investigated and the thermodynamic activation parameters were calculated. The rate constant of the first step of the overall process increases when the acidity is raised, while the second step is slowed down. The negative value of ΔS≠ (−100.9 J mol−1 K−1) measured for the second step suggests the participation of water in the transition state.