McClelland, Robert A.; Seaman, N. Esther; Duff, James M.; Branston, R. E. published the artcile< Kinetics and equilibrium in the ammonolysis of substituted phthalimides>, Quality Control of 118-45-6, the main research area is ammonolysis phthalimide substituent effect; hydrolysis phthalimide kinetics mechanism; cyclization phthalamide kinetics mechanism.
The basic hydrolysis kinetics of the title compounds (I; R = H, 4-NO2, 4-Cl, 4-Me3C, 3-NO2, 3-Me, 3-Me3Si), to phthalamic acids, show that it involves 2 mechanisms, one of which is first order each in I and OH- and one of which (important in very concentrated MeOH) is first order in I and second order in OH-. The ammonolysis kinetics of I (R ≠ 3-Me, 3-Me3Si) show that the mechanism involves a rate-determining breakdown of the anionic form of the tetrahedral intermediate derived by the addition of NH3 to I; the ammonolysis is reversible. The phthalamide hydrolyzes to the phthalamic acid via cyclization to an intermediate I, which is observed in concentrated base, where its formation from phthalamide is more rapid than its subsequent hydrolysis. Rate constants for the cyclization (the microscopic reverse of the ammonolysis) together with those for ammonolysis provide the equilibrium constant for the ammonolysis reaction. The ammonolysis kinetics of I (R = 3-Me) show that it is reversibly converted to the phthalamide and simultaneously undergoes an irreversible hydrolysis. The ammonolysis of I (R = 3-Me3Si) occurs more quickly than hydrolysis but the equilibrium is so unfavorable that even in concentrated NH3 only a small amount of the phthalimide is formed.
Canadian Journal of Chemistry published new progress about Ammonolysis. 118-45-6 belongs to class chlorides-buliding-blocks, and the molecular formula is C8H3ClO3, Quality Control of 118-45-6.
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