| Abstract: | We studied the formation and hydrolysis of the Schiff base of pyridoxal-5′ -phosphate (PLP) and n-dodecylamine (DOD) by kinetic methods and found the formation rate constants to be much larger than those reported for related systems. This can be ascribed to the occurrence of local concentration of charges in the vicinity of the carbinolamine, which stabilizes the corresponding transition state of the dehydration reaction. On the other hand, the hydrolysis rate constants of our system were considerably smaller as a result of the 12-atom hydrocarbon chain acting as a bulky hydrophobic rest protecting the imine bond from attack by water. |
