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Kinetics, Medium and Deuterium Isotope Effects in the Alkaline Decomposition of Quaternary Phosphonium Salts

Kinetic measurements of the alkaline decomposition of tetraphenylphosphonium chloride were made in a series of acetone-water mixtures at 25—50 °C. The third-order rate increases remarkably, up to 1.2 · 106 times, with addition of acetone. The rate constant is expressed by k' = 19.6 exp (— 33.5 [kcal/mole]¡RT) I2 mole-2 sec"1 in water and k' = 12.2 exp (—14.6 [kcal/mole]¡RT) I2 mole"2 sec"1 in 80% acetone. The activation energy decreased progressively with increasing acetone content and the change was described in the light of solvation phenomena and internal solvent structure. The solvent deuterium isotope effect showed