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Bulletin of the Korean Chemical Society (BKCS)

ISSN 0253-2964(Print)
ISSN 1229-5949(Online)
Volume 8, Number 2
February 20, 1987 

Kinetic Studies on the Reduction of 1-Benzyl-3-cyanoquinolinium Cations by Sodium Borohydride and the Applicability Marcus Theory
In-Sook Han*, Chang Kiu Lee, In Sup Han
The reduction of a series of 1-substituted benzyl-3-cyanoquinolinium ions (p-CH3, H, p-Br, m-F, p-CN) by sodium borohydride has been investigated. In all cases the products from these reactions were found to be 1, 2-dihydroquinolines over 82% yields. Rates of reduction were measured in basic condition and in solvent system consisting of 4 parts of isopropyl alcohol and 1 part of water by volume. Second order rate constants were obtained for these reactions. When the ratio of [OH-] to [BH4-] becomes large the observed rate constants (kobs) decrease by a small factor. Reaction scheme and rate law are discussed. Brønsted α (= (d ln k)/(d ln K)) obtained by using the value of equilibrium constant K, which was obtained previously, was not 0. Instead, a value of 0.36 was obtained which indicated that the reduction by borohydride was structure-dependent according to the Marcus formalism even though the reaction rate was close to the diffusion limit.
79 - 83
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