1971 Volume 44 Issue 3 Pages 791-793
Studies have been made of the kinetics of the reactions of thiol acids (thiostearic acid and thioacetic acid) with anilines, such as aniline and p-methoxy-, p-ethoxy-, p-methyl-, m-methyl-, p-chloro, m-chloro-, and m-nitrosubstituted anilines, in a chlorobenzene solution. The rate is given by k(RCO–SH) (X-C6H4-NH2). The activation energy for the reaction of thiostearic acid with aniline is 5.3 kcal/mol. The Hammett plots give a straight line, with a value of ρ=−2.40 for the reactions of thiostearic acid or thioacetic acid with the anilines; the mechanism of the reaction of thiol acids with anilines is discussed.
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