THE DECOMPOSITION OF 2-METHYL-Δ2-OXAZOLINE IN AQUEOUS SOLUTION

Abstract

Nuclear magnetic resonance has been used to follow the decomposition of aqueous solutions of 2-methyl-Δ²-oxazoline (0.29 M) at constant pH values in the range −1 to 14. The decomposition is first order with respect to total oxazoline at any specific pH, but deviates from the simple reaction of water with the protonated species above pH 5. At neutral pH values this is shown to be partially due to a second reaction involving 2-methyl-Δ²-oxazoline and O-acetylethanolamine which yields N-2-acetoxyethyl N′-2-hydroxyethyl acetamidate. The decrease in rate constant at pH < 2 is accounted for by variation in the water concentration, which is related to the acidity function. A kinetic expression is derived for the decomposition over the whole pH range studied. The decomposition of the amidate is also discussed.