Hydration of Pyridine Bases in Benzene

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Abstract
Hydration of pyridine bases in benzene has been studied by partition at 25 °C, the total concentration of pyridine bases being less than 1.0 M in benzene. The studied pyridine bases include pyridine, 2-methylpyridine, 4-methylpyridine, 2,6-dimethylpyridine, 3,5-dimethylpyridine, 2,4,6-trimethylpyridine, 2-chloropyridine, 2-bromopyridine, 3-bromopyridine and 2,6-dibromopyridine. Hydrated species with different composition are formed: the composition of the hydrated species (base to water ratio) is as follows: (1 : 2) for 2,6-dibromopyridine, (1 : 1) and (1 : 2) for 2-chloro- and 2-bromopyridine, (1 : 1) and (2 : 1) for 3-bromopyridine, (1 : 1), (1 : 2) and (2 : 1) for 4-methylpyridine and pyridine itself, and (1 : 1), (1 : 2), (2 : 1) and (2 : 2) or (2 : 3) for the other methyl derivatives. A linear free energy relationship has been observed between the hydration in benzene for the monomer monohydrate and the protonation in water of the corresponding base.

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