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1H NMR Study of the Rates and Isotope Effects of the NADH Model Hydride Transfer Reaction

✍ Scribed by G.X. He; A. Blasko; T.C. Bruice

Publisher
Elsevier Science
Year
1993
Tongue
English
Weight
364 KB
Volume
21
Category
Article
ISSN
0045-2068

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✦ Synopsis

The kinetics of reaction of ([4,4-(\mathrm{H}, \mathrm{H})]-\mathrm{BzNADH}) and ([4,4-(\mathrm{H}, \mathrm{D})]-\mathrm{BzNADH}) with methyl benzoylformate ( (\mathrm{MBF}) ) and (p)-benzoquinone ((\mathrm{BQ})) in (\mathrm{CD}{3} \mathrm{CN}) and in the presence of (\mathrm{Mg}{(}\left(\mathrm{ClO}{4}\right){2}) has been studied by 'H NMR spectroscopy. Prior investigations of mechanisms of 1,4dihydropyridine oxidations have employed the less informative methods of uv/vis spectrophotometry. No 'H NMR evidence was found for the hydration of BzNADH nor for the reaction of starting (\mathrm{BzNADH}) and product (\mathrm{BzNAD}{ }^{+})which would lead to isotope scrambling in the course of reaction. Calculated values of PKIE and SKIE suggest a mechanism change from a single step (\mathrm{H}^{-})transfer for BzNADH oxidation with MBF to a multistep (\mathrm{e}^{-}, \mathrm{H}^{+}), (\mathrm{e}^{-})transfer for BzNADH oxidation with (\mathrm{BQ} . \quad 1993) Academic Press, Inc.

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