The Substituent Effect. II. Normal Substituent Constants for Polynuclear Aryls from the Hydrolysis of Arylcarbinyl Benzoates
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The rates of the alkaline hydrolysis of 9 polynuclear arylcarbinyl benzoates were measured in 70% (v/v) aqueous acetone at 25°C. The new set of σ<SUP>0</SUP> values for polynuclear aryls was obtained, using the ρ<I><SUB>m</SUB></I> value established by the hydrolysis of <I>m</I>- and <I>p</I>-substituted-benzyl benzoates. In the present reaction, it is possible to assume that the peri-hydrogen steric effect is practically absent, bacause <I>o</I>-tolyl derivative gives a σ<SUP>0</SUP> a value comparable with that of <I>p</I>-tolyl, and 1-naphthyl with that of 2-naphthyl. The set thus obtained can be successfully described in terms of two components; self-atom polarizability and Streitwieser's inductive index, ∑<I>r<SUB>ij</SUB></I><SUP>−1</SUP>.
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