Abstract
Analysis of kinetic behavior of isomeric Z-amidoximes and their Z-ions in reactions with 4-nitrophenyl-4-toluenesulfonate, diethylphosphate, and diethylphosphonate was performed in the framework of Bronsted relationship. The reactivity of amidoximate anions with respect to the mentioned substrates is comparable to that of typical α-nucleophiles, oximate ions. The α-effect decreased with the growing basicity of amidoximate ions, and for compounds with pKa>12.0 it was totally lacking. The high nucleophilic activity of neutral amidoximes and their anionic forms was ascribed to the cyclic structure of the transition state involving two kinds of assistance: general acidic, and basic catalysis. A unique feature of amidoximes as α-nucleophiles consists in their ability to perform efficient cleavage of ecotoxic substrates in a wide pH range, from basic to acid media.
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