The reaction of iodine with 9-methylacridine: formation of polyiodide salts and a charge-transfer complex

The reaction of iodine and 9-methylacridine in methylene chloride results not in the formation of a charge-transfer complex as with acridine, but in the iodine-rich salt ICH2C13H8N-“H]4(I8)(I5)2, 8, where a proton on the methyl group has been replaced by an iodine. In toluene, the reaction produces both a charge-transfer complex ICH2C13H8N-“I2, 9, and a salt CH3-“acridine(H)]2(I7)(I5), 10. Polyiodide salt formation can be explained by the availability of a facile reaction pathway from the aryl radical cation which results from initial oxidation by I2.