Kinetics and mechanism of the cleavage of n-methoxyphthalimide (NMPT) in the presence of buffers of tris (hydroxymethyl)amino methane (tris) and 1,4-diazabicyclo[2.2.2]octane (DABCO)

The magnitude of hydroxide ion-catalyzed second-order rate constant (k_OH) for hydrolysis of N-methoxyphthalimide (NMPT) supports the conclusion that the rate law for pH-independent hydrolysis of N-hydroxyphthalimide (NHPTH) is rate = k_OH[HO^-][SH] where SH represents nonionized NHPTH. The second-order rate constants for the reactions of NMPT with DABCO and Tris are (59.7 ± 6.9) x 10^-3 and (11.9 ± 2.3) x 10^-4 M^-1 s^-1, respectively. This revised version was published online in June 2006 with corrections to the Cover Date.