Gas-phase H/D exchange between arenium ions and selected bases. The site of protonation of simple aromatics

A radiolytic technique was employed to describe the exchange of hydrogen and deuterium between substituted arenium ions and various bases containing at least one hydrogen at the active site. The exchange of hydrogen and its isotope is dependent on both the arenium ion and the base. Nuclear magnetic resonance analysis reveals that the protonation reaction involves the most basic ring positions.