The Kinetics and Mechanism of Nucleophilic Addition of Thioglycolic Acid to ${\beta}$-Nitrostyrene Derivatives

The Kinetics and Mechanism of Nucleophilic Addition of Thioglycolic Acid to ${\beta}$-Nitrostyrene Derivatives

The rate constants of the nucleophilic addition of thioglycolic acid to the derivatives $(H,\;p-CH_3,\;p-CH_3O,\;p-Cl,\;p-NO_2)$ of ${\beta}$-nitrostyrene were determined by ultraviolet spectrophotometry. The rate equations which can be applied over a wide pH range were obtained. Therefrom a reaction mechanism was proposed. Above pH 8.5 sulfide anion adds to the double bond (Michael type addtion). However, below pH 8.5, the neutral molecule and $HSCH_2COO^{\theta}$ add to the double bond.

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