The solvolyses of p-tolyl chlorothionoformate and p-chlorophenyl chlorothionoformate are studied in a variety of organic mixtures of widely varying nucleophilicity and ionizing power values. This solvolytic data is accumulated at 25.0 °C using the titration method. An analysis of the rate data using the extended (two-term) Grunwald-Winstein equation, and the concept of similarity of substrates based on their l/m ratios, shows the occurrence of simultaneous side-by-side addition-elimination and unimolecular SN1 mechanisms.
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