Kinetic studies on the Reaction of Cyanuric Chloride with Amines

Abstract

The individual steps in the reactions of cyanuric chloride with n-butyl amine in N-methyl pyrrolidone (NMP) and with morpholine in isopropanol (i-PrOH) were followed kinetically. The ratio of the exchange rates of the first, the second and the third chlorine atom was unexpectedly high in both cases. The reactions of n-butylamino dichlorotriazine with several amines were studied kinetically both in NMP and in i-PrOH. Linear free-energy relationships exist both between our values in NMP and in isopropanol and between our values and reaction rates of p-nitro fluorobenzene with the corresponding amines (in DMSO) determined by Suhr.