Kinetic Study on the Reaction of p-Nitrophenyl Acetate with 6-Substituted 2,4-Diamino-1,3,5-triazines

The reactions of p-nitrophenyl acetate (1) with six 6-substituted 2,4-diamino-1,3,5-triazines, (2a–2f), were kinetically investigated in aqueous DMSO or in water at 30 °C. It was found that the reaction rate R could be expressed according to the equation R=(k0+kN[2])[1], and that Bronsted-type plots for the kN-reaction give a straight line with a slope (β) of 1.05. The solvent deuterium isotope effect was not observed in this reaction [kN(H)⁄kN(D)=1.0–1.15]. Furthermore, the isolated reaction product was 2-acetylamino-4-amino-6-methyl-1,3,5-triazine (4c), which was formed by a nucleophilic attack of 2c to 1. From these results, the mechanism for this nucleophilic reaction is discussed.

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