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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 <...
Kinetic investigation of the acid hydrolysis of N-(methoxyprop-2-yl)benzanilide (1) was performed in 8.84M HCl and/or DCl at 75.1 o C. The formation of 2-(N-phenylamino)propanol (4) was explained and the mechanism, involving an initial ether cleavage anchimerically assisted by the amide group, was clarified. The overall process evolves through three steps involving two intermediates. The rate...
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