87875-77-2Relevant academic research and scientific papers
Kinetics and mechanism of the bromination of 4-pyridone and related derivatives in aqueous solution
Tee, Oswald S.,Paventi, Martino
, p. 2556 - 2562 (2007/10/02)
The kinetics of bromination of 4-pyridone and selected derivatives have been measured in aqueous solutions in the pH range 0-9, at 25 deg C.The tautomeric system 4-pyridone 4-hydroxypyridine (1a 2a) reacts with bromine via the predominant (pyridone) tautomer at pH 6. 3-Bromo-4-pyridone behaves similary.The kinetics also reveal that the facile dibromination of 4-pyridone occurs because at most pH's the monobromo derivative is actually more reactive towards bromine by virtue of its lower pKa values.From the point of view of reactivity the 4-pyridones and their anions behave as substituted phenoxide ions. 4-Methoxypyridine does not undergo bromination under comparable conditions, but rather forms a complex with bromine.
