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The role of tetraalkylammonium salts in the electro-reduction of ketones. Part II: The reduction of acetophenone in an aprotic environment

✍ Scribed by W. J. M. van Tilborg; C. J. Smit; R. A. van Santen

Book ID
104588176
Publisher
Elsevier Science
Year
2010
Tongue
English
Weight
591 KB
Volume
98
Category
Article
ISSN
0165-0513

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✦ Synopsis

Abstract

A polarographic study of the electro‐reduction of acetophenone in dry acetonitrile has revealed that under strictly anhydrous conditions the carbonyl compound can be reduced only if tetraalkylammonium ions are present. The role played by these ammonium ions is discussed. It is concluded that the catalytic effect of the ammonium ions has to be related to an increased polarization of the carbonyl double bond being induced during collision of the ammonium ions with the carbonyl compound. At high ammonium ion concentrations, however, the effect of this catalysis becomes smaller due to preferential adsorption of the ammonium ions on the electrode surface, as a result of which the carbonyl compound is displaced from the direct vicinity of the electrode.

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