The Rate and Equilibrium Constants for N-, O-Acyl Transfer

V. I. Rybachenko¹, K. Yu. Chotii¹, V. V. Kovalenko¹, and G. Shreder²

¹ Litvinenko Institute of Physicoorganic and Coal Chemistry, National Academy of Sciences of Ukraine,
Donetsk, 83114 Ukraine

² Faculty of Chemistry, Adam Mitskevich University, Poznan, Poland

Received April 12, 2002

Abstract—Reactions with dimethylcarbamoyl group transfer from N-acylpyridinium salts to pyridine
Noxides and from N-acyloxypyridinium salts to pyridines in acetonirile solutions were studied. Their rate and
equilibrium constants and activation parameters were determined. The reactions were shown to be one-step and
to follow the S_N2 mechanism. Equations relating the rate and equilibrium parameters of the N–O and O–N acyl
transfer reactions to the basicity of the nucleophile and outgoing group were obtained.

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