Abstract
AbstractThe kinetics of the reactions of o‐substituted phenylmercuric chlorides, o‐RC6H4HgCl (R = CH3, H, C2H5O, CH3O, C6H5, F, COOC2H5, Cl, Br, CF3, NO2), with hydrochloric acid in 80% aqueous dioxane in the presence of NaI were studied. The reactions are of the first order. The rate constant at 40°C decreases in the order of R: CH3 > H > C2H5O > CH3O > C6H5 > F > COOC2H5 > Cl > Br > CF3 > NO2. The analysis of effects of those o‐substitutes is carried out through multiple regression of log k/kH with the corresponding inductive substituent constants σI and the various resonance substituent constants σ, σR(BA), σ, σ and σx, and the corresponding Swain–Lupton field effect constant $\Im $ and resonance effect constant $\Re $. The results showed that o‐substituent intramolecular coordination with the neighbor mercury (field effect) is the main effect in effects of o‐substituents on rate of the SE1 protonolysis. Copyright © 2007 John Wiley & Sons, Ltd.
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