Molecular orbital correlation of arylmethyl chloride atom abstraction by stannyl radicals

Abstract

A series of monochloromethylated polycyclic benzenoid hydrocarbons have been treated with triphenyltin hydride and AIBN initiator at 70°C. Under these conditions the only observable reaction is reduction of the starting materials to methylarenes. A significant range of relative rates (factor of 40) has been found among the compounds studied. All relative rates yielded an excellent correlation when plotted against PPP-SCF calculated energy differences. The present works shows the ability of such calculations to treat processes involving nucleophilic radicals.