Kinetics, stoichiometry and mechanism in the bromination of aromatic heterocycles. IV. Aqueous bromination of Imidazo[1,2-a]pyridine
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The reaction of imidazo[l,2-a]pyridine with bromine has been studied in dilute acidic aqueous solution at 25�C. The bimolecular rate coefficient for attack by Br2 on the molecular substrate at the 3-position is found to be K�bi = 1.30(� 0.05) x 109 dm3 mol-l s-l We find pK.(imidazo[l,2-a]pyridine-H+, aq., 25�C) = 6.65 and pK,(3-bromoimidazo[l,2-alpyridine-H+, aq.,25�C) = 4.95. The latter compound reacts with bromine in aqueous acetate buffer at pH4.
1974 ◽
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