Kinetics of Competing Reactions of N-aryl-4-chloro-1,8-naphthalimides with Primary Amines

Abstract

The 4-amino-1,8-naphthalimide ring system is the basis of a number of important fluorophores due to its chemical and photochemical stability. In addition, the conventional wisdom states that when the imide ring is formed by treating naphthalic anhydrides with primary amines, the new heterocyclic ring is resistant to attack by nucleophiles. It has been discovered that this is not the case, and that the imide ring of 4-chloro-N-aryl-1,8-naphthalimide is, in fact, susceptible to attack by primary amine nucleophiles. The kinetics of this reaction have been studied in n-butylamine and show a Hammet plot with excellent linearity. The purpose of this project was to examine the effects of alcohol solvents and tertiary amine co-solvents on the reactions of 4-choro-N-aryl-1,8-naphthalimides on the rates of the displacement reaction with n-butylaminie.