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Kinetics and mechanism of aminolysis of aliphatic esters in aprotic solvents

✍ Scribed by Agu-Tõnis Talvik; Ants Tuulmets; Evi Vaino

Publisher
John Wiley and Sons
Year
1999
Tongue
English
Weight
52 KB
Volume
12
Category
Article
ISSN
0894-3230

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✦ Synopsis

Kinetic studies were carried out on the aminolysis reactions of substituted aliphatic esters in a variety of aprotic solvents. The reaction rate is strongly affected by inductive and steric effects of substituents in the acyl group, rising more than 10 4 -fold from cyanoacetate to trifluoroacetate. The quantitative treatment of solvent effects revealed a rate decrease by the polarity and p-basicity of the solvents, and also an accelerating effect of the polarizability of solvents. Cyclic transition states were assumed for both the first and second-order (in amine) reactions.

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