The kinetics of tritium-hydrogen exchange between xanthine,theophylline,caffeine and water

Isotopic hydrogen exchange at C-8 of xanthine, theophylline and caffeine in water has been studied at several temperatures and constant pH. The rates of detritiation of these compounds have been determined over a pH range at constant temperature. The rate-pH profiles for theophylline and caffeine are interpreted in terms of rate determining attack by hydroxide ion on protonated substrate. For caffeine and xanthine at high pH an additional mechanism involving hydroxide catalysed exchange of the neutral compound is suggested.