Abstract
The hydrolysis of 2‐chloro‐3,5‐dinitropyridine by sodium hydroxide in the presence of micelles of cetyltrimethylammonium bromide (CTABr), cetyltrimethylammonium chloride (CTACl) and sodium dodecyl sulfate (SDS) has been studied. The reaction follows a consecutive reaction path involving the formation of a long‐lived intermediate 3 and finally giving the product, 3,5‐dinitro 2‐pyridone 2. The mechanism follows an addition of the nucleophile, ring opening and ring closure (ANRORC) reaction path. The rate constant was observed to be first‐order dependent on [OH−]. The rate of reaction increased on increasing [CTABr] and, after reaching to the maxima, it started decreasing. The anionic SDS micelles inhibited the rate of hydrolysis. The results of the kinetic experiments were treated with the help of the pseudophase ion exchange model and the Menger–Portnoy model. The added salts, viz. NaBr, Na‐toluene‐4‐sulphonate, and (CH3)4NBr on varying [CTACl] and [SDS] inhibited the rate of reaction. The various kinetic parameters in the presence and absence of salts were determined and are reported herewith. Copyright © 2011 John Wiley & Sons, Ltd.
2‐chloro‐3,5‐dinitropyridine is hydrolyzed by sodium hydroxide to give 3,5‐dinitro 2‐pyridone. The reaction proceeds through ANRORC reaction mechanism with the formation of a long lived anion. Addition of CTABr micelles catalyzed the rate of hydrolysis, whereas SDS inhibited the rate of reaction. The observed results are explained on the basis of Menger–Portnoy model.