350221-10-2Relevant academic research and scientific papers
Acidity effect on the cleavage of ether function intramolecularly assisted by the amide group. Part 5
Arcelli, Antonio,Cecchi, Romina,Porzi, Gianni,Rinaldi, Samuele,Sandri, Sergio
, p. 6843 - 6846 (2007/10/03)
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.
Mechanistic investigation of an anomalous anchimeric assistance in the acid hydrolysis of the ether linkage. Part 4
Arcelli, Antonio,Cecchi, Romina,Porzi, Gianni,Rinaldi, Samuele,Sandri, Sergio
, p. 4039 - 4043 (2007/10/03)
Kinetic investigation of the acid hydrolysis of N-(methoxyprop-2-yl)benzanilide (1) was performed in 8.84 M HCl and/or DCl at 75.1°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 constants of the individual processes have been determined by UV and 1H NMR spectroscopic techniques.
