Journal of the Chemical Society. Perkin transactions II p. 371 - 378 (1985)
Update date:2022-08-18
Topics:
Fukuzumi, Shunichi
Nishizawa, Nobuaki
Tanaka, Toshio
The effects of Mg2+ ion on hydride-transfer reactions from an NADH model compound, 1-benzyl-1,4-dihydronicotinamide (BNAH),to a series of p-benzoquinone derivatives (Q) as well as on the redox potentials of BNAH and Q in acetonitrile have been examined.The Mg2+ ion shows both accelerating and retarding effects on the hydride transfer reactions depending on the p-benzoquinone derivative and the Mg2+ ion concentration.Such dual effects of the Mg2+ ion have been well correlated with the change of the redox potentials of BNAH and Q in the presence of Mg2+ ion since it has been found that there is a simple correlation between the logarithm of the rate constat and the difference of the redox potentials between BNAH and Q in the absence and presence of Mg2+ ion.It is shown that a proposed reaction mechanism involving electron transfer from BNAH to Q followed by proton transfer from BNAH+. to Q-. in the rate-determining step of the hydride-equivalent transfer provides a quantitative evaluation of the single and unified correlation between the logarithm of the rate constant and the difference between the redox potentials of BNAH and Q in the absence and presence of Mg2+.The effect of Mg2 ion on the primary kinetic isotope effects on hydride transfer from BNAH to Q is also shown to be consistent with the proposed reaction mechanism.Moreover, a ternary complex involving BNAH,Mg2+ ion, and Q as a reaction intermediate prior to electron transfer from BNAH to Q has been detected for the first time.
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