Abstract
A series of 5-substituted 3-cyanotoluenes was synthesized, and the relative rates of N-bromosuccinimide bromination were determined in benzene at 80C. The resulting {sigma}{sub F}{sup {sm bullet}} values of meta Me, H, Br, NO{sub 2}, and CN were found to be 0.03, 0.00, {minus}0.03, {minus}0.04, and {minus}0.10, respectively. Of these meta substitutents, all but methyl were found to be destabilizing to the intermediate benzyl free radical. These meta substituent results are consistent were reported {sigma}{sub {alpha}}{sup {sm bullet}} and {alpha}{sub c}{sup {sm bullet}} values and cast doubt upon reports that assume meta substituents have no influence on free-radical stability.
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