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

Abstract

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as with acridine, but in the iodine-rich salt [ICH₂C₁₃H₈N–H]₄(I₈)(I₅)₂, 8, where a proton on the methyl group has been replaced by an iodine.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.