Isotope Effects in the Electrochemical Reduction of Oxalic Acid-D2 and Benzoic Acid-D |
| |
| Authors: | P Kränke H Matschiner R Trutschel M Wahren |
| |
| Institution: | 1. Wissenschaftler-Integrations-Programm , Leipzig;2. Fachbereich Chemie, Martin-Luther-Universit?t Halle-Wittenberg , Germany |
| |
| Abstract: | Abstract The electrochemical reduction of model carboxylic acid at lead cathodes in deuterated media was studied for potential use in the synthesis of special deuterated compounds. Oxalic acid-d2 in D2O gives good yields of glyoxylic acid-d2. An unexpected large isotope effect of 5.3 ± 1.7 was found in this reaction, leading to significant depletion of deuterium content in the aldehyde group. Benzoic acid-d in CD3OD/diluted D2SO4 yields benzyl alcohol-d, 7,7-d2. The isotope effect of 2.4 ± 1.0 is within the expected range. No deuterium is incorporated into the aromatic nucleus. Essentially unlabelled benzyl alcohol is obtained in CD3OH/dil. H2SO4. |
| |
| Keywords: | Benzoic acid benzyl alcohol deuterium compounds deuterium NMR electrochemical reduction glyoxylic acid isotope effects oxalic acid |
|
