Interaction of 2,3-dichloro-1,4-naphthoquinone with n-butylamine in halocarbon solvents

Abstract

The rapid interaction between 2,3-dichloro-1,4-naphthoquinone (DClNQ) and n-butylamine results in the formation of 2N( n-butylamino)-3-chloro-1,4-naphthoquinone as the final product. The reaction is found to proceed through the initial formation of charge-transfer (CT) complex as an intermediate. The final product of the reaction has been isolated and characterized using FTIR, H 1 and C 13 NMR spectroscopy, mass spectrometry, and elemental analysis. The rate of formation of product has been measured as a function of time in different halocarbon solvents, viz., chloroform, dichloromethane and 1:1 (v/v) mixture of two solvents. The pseudo first order and second order rate constants at various temperatures for the transformation process were evaluated from the absorbance time data. The activation parameters ( E a, Δ S #, Δ H #, and Δ G #) were obtained from temperature dependence of rate constants. The influence of dielectric constant on the properties of reaction was discussed and the probable course of reaction is presented.