Reactions of Aliphatic Amines with p-Benzoquinone and Its Chloro Derivatives

Abstract

Abstract The reactions of various aliphatic amines with p-benzoquinone and its chloro-derivatives were studied by detecting reaction intermediates by means of the rapid scan spectrophotometric method. A detailed kinetic study on the reaction intermediate and the final product was made for the system including n-butylamine and chloranil in ethanol; the result shows that the system produces 2,5-di-n-butylamino-3,6-dichloro-p-benzoquinone via the chloranil anion and the n-butylamine cation with the rate constant of 9.8×102 sec−1mol−1l at 275.2°K. On the basis of reaction mechanisms, the reactions of various aliphatic amines with p-benzoquinone and its chloroderivatives were classified into five types. Stabilization energies due to the amino-substitution of p-benzoquinone were calculated by the composite molecule method; the result shows that the 2,5-derivative is most stable among the disubstituted p-benzoquinones.