Elucidation of the role of the complex in hydride transfer reaction between methylene blue and 1-benzyl-1,4-dihydronictinamide by effect of γ-cyclodextrin

The kinetics of the hydride transfer reaction between Methylene Blue (MB⁺) and　1-benzyl-1,4-dihydronicotinamide (BNAH) were studied in 10 % ethanol-90 % water mixed solvents containing β- and γ-cyclodextrins (β-CD and γ-CD). The pseudo-first order rate constant shows kinetic saturation at high initial concentration of BNAH. This indicates the formation of a complex between MB⁺ and BNAH. The reaction was suppressed by addition of β-CD, but enhanced by addition of γ-CD. MB⁺ and BNAH were separately accommodated within the β-CD cavity and the cavity walls may protect the activity site of the reactants. On the other hand, in the MB⁺-BNAH-γ-CD system, the inclusion of the complex between MB+ and BNAH with γ-CD occurred. This effect of γ-CD can distinguish between the productive and non-productive nature of the complex.

Digital Object Identifer:10.1007/s10847-005-8119-5
Published with permission from the copyright holder. This is the author's copy of the work, as published in Journal of Inclusion Phenomena and Macrocycle Chemistry, April 2006, Volume 54, Issue 3-4, Pages 233-239.
Publisher URL: http://dx.doi.org/10.1007/s10847-005-8119-5
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