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Bulletin of the Korean Chemical Society (BKCS)

ISSN 0253-2964(Print)
ISSN 1229-5949(Online)
Volume 6, Number 2
February 20, 1985 

Studies on the Quaternization of Tertiary Amines (Ⅳ). Kinetics and Mechanism for the Reaction of Substituted Phenacyl Tosylates with Substituted Pyridines
Oh Seuk Lee, Soo Dong Yoh
Substituent effects of substrate and nucleophile for the reaction of substituted phenacyl tosylates with pyridines were determined conductometrically in acetonitrile. Activation parameters for these reactions were also calculated. The substituent effects in nucleophile were increased with electron-donating power of pyridines and Brønsted linear relationship was shown. Rate constant was increased by both electron-donating and electron-attracting groups in the substrate. It seems that dissociative SN2 ("loose" transition state) mechanism is operating in the case of electron-donating substituents while associative SN2 ("tight" transition state) mechanism is operative in the case of electron-attracting substituents.
99 - 102
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