Bulletin of the Chemical Society of Japan
Online ISSN : 1348-0634
Print ISSN : 0009-2673
ISSN-L : 0009-2673
Coenzyme Models. XII. Kinetics and Mechanisms of 1,4-Dihydro-nicotinamide Reduction of Carbon-Carbon Double Bonds. Influence of Added Mg2+ Ion and Acetic Acid
Seiji ShinkaiYumiko KusanoToyoko IdeTakaaki SoneOsamu Manabe
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1978 Volume 51 Issue 12 Pages 3544-3548

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Abstract

Nonenzymatic dihydronicotinamide reduction of carbon-carbon double bonds occurs with the aid of Mg2+ ion or acetic acid. The role of Mg2+ ion and acetic acid is discussed on the basis of spectral studies, kinetic measurements, and product analyses. The addition of Mg2+ ion caused the shift of the NMR peak of substrate α-proton to lower field, and the magnitude was parallel to the yield of reduced methylene derivatives. Kinetic studies suggested that the dihydronicotinamide reduction in the presence of Mg2+ ion is most reasonably understood by assuming a competitive complexation of dihydronicotinamide and substrate with Mg2+ ion. On the other hand, acetic acid aids the reduction by means of general acid catalysis, but an alternative mechanism is suggested for the reduction of benzylidenemalononitrile.

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