Intramolecular catalysis in the detritiation of 2′,6′-dihydroxyacetophenone and 2′-hydroxyacetophenone

Abstract

The kinetics of detritiation of 2′,6′-dihydroxyacetophenone have been studied at 25° in aqueous buffers and sodium hydroxide solutions in the pH range 6.0–13.8, and similar studies were made for 2′-hydroxyacetophenone between pH 12 and 13.8. The rates of the intramolecular processes for the two compounds have been determined, and do not indicate any special effects arising from simultaneous acid and base catalysis in the monoanion of 2′,6′-dihydroxyacetophenone. The results suggest an unusually large hydrogen isotope effect for intramolecular proton transfer in the anion of 2′-hydroxyacetophenone.