The Journal of organic chemistry

Kinetics and mechanism of the pyridinolysis of phenacyl bromides in acetonitrile

HJ Koh, KL Han, HW Lee, I Lee

Index: Koh, Han Joong; Han, Kwang Lae; Lee, Hai Whang; Lee, Ikchoon Journal of Organic Chemistry, 2000 , vol. 65, # 15 p. 4706 - 4711

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Citation Number: 42

Abstract

Kinetic studies of the reactions of substituted phenacyl bromides (YC6H4COCH2Br) with pyridines (XC5H4N) are carried out in acetonitrile at 45.0° C. A biphasic Brønsted plot is obtained with a change in slope from a large (βX≌ 0.65-0.80) to a small (βX≌ 0.36-0.40) value at p K a°= 3.2-3.6, which can be attributed to a change in the rate-determining step from breakdown to formation of a tetrahedral intermediate in the reaction path as the ...