Studies on the decomposition of tetra-alkylammonium salts in solution. Part III: Interpretation of Hammett correlations

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Abstract
Hammett free energy correlations are reported for the decomposition reactions of tetra-alkylammonium halides in chloroform and acetone solution. All the salts contained a substituted benzyl group attached to the nitrogen atom and decomposed to yield a benzyl iodide and dimethylaniline as the only products.The curved Hammett plots for para-substituted benzyl compounds are compared to the linear plot found previously for a series of salts each containing a para-substituted phenyl group, and it is concluded that curved Hammett plots cannot be used as evidence for a change of mechanism, unless direct conjugative effects between substituent and reaction site are absent.

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