Hydrogen Bonding Enhances the Electrochemical Hydrogenation of Benzaldehyde in the Aqueous Phase

Udishnu Sanyal, Simuck F. Yuk, Katherine Koh, Mal Soon Lee, Kelsey Stoerzinger, Difan Zhang, Laura C. Meyer, Juan A. Lopez-Ruiz, Abhi Karkamkar, Jamie D. Holladay, Donald M. Camaioni, Manh Thuong Nguyen, Vassiliki Alexandra Glezakou, Roger Rousseau, Oliver Y. Gutiérrez, Johannes A. Lercher

Research output: Contribution to journalArticlepeer-review

Abstract

The hydrogenation of benzaldehyde to benzyl alcohol on carbon-supported metals in water, enabled by an external potential, is markedly promoted by polarization of the functional groups. The presence of polar co-adsorbates, such as substituted phenols, enhances the hydrogenation rate of the aldehyde by two effects, that is, polarizing the carbonyl group and increasing the probability of forming a transition state for H addition. These two effects enable a hydrogenation route, in which phenol acts as a conduit for proton addition, with a higher rate than the direct proton transfer from hydronium ions. The fast hydrogenation enabled by the presence of phenol and applied potential overcompensates for the decrease in coverage of benzaldehyde caused by competitive adsorption. A higher acid strength of the co-adsorbate increases the intensity of interactions and the rates of selective carbonyl reduction.

Original languageEnglish
JournalAngewandte Chemie - International Edition
DOIs
Publication statusAccepted/In press - 2020

Keywords

  • electrochemistry
  • electron transfer
  • hydrogen bonding
  • reduction
  • supported catalysts

ASJC Scopus subject areas

  • Catalysis
  • Chemistry(all)

Fingerprint Dive into the research topics of 'Hydrogen Bonding Enhances the Electrochemical Hydrogenation of Benzaldehyde in the Aqueous Phase'. Together they form a unique fingerprint.

Cite this