@article{f43f2d5fb829498eba4d3e60d13f1e9f,
title = "Hydrogen Bonding Enhances the Electrochemical Hydrogenation of Benzaldehyde in the Aqueous Phase",
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.",
keywords = "electrochemistry, electron transfer, hydrogen bonding, reduction, supported catalysts",
author = "Udishnu Sanyal and Yuk, {Simuck F.} and Katherine Koh and Lee, {Mal Soon} and Kelsey Stoerzinger and Difan Zhang and Meyer, {Laura C.} and Lopez-Ruiz, {Juan A.} and Abhi Karkamkar and Holladay, {Jamie D.} and Camaioni, {Donald M.} and Nguyen, {Manh Thuong} and Glezakou, {Vassiliki Alexandra} and Roger Rousseau and Guti{\'e}rrez, {Oliver Y.} and Lercher, {Johannes A.}",
note = "Funding Information: The research described in this paper is part of the Chemical Transformation Initiative at Pacific Northwest National Laboratory (PNNL), conducted under PNNL's Laboratory Directed Research and Development Program. D.M.C. and J.A.L. were supported by the U.S. Department of Energy (DOE), Office of Science, Office of Basic Energy Sciences, Division of Chemical Sciences, Geosciences and Biosciences (Transdisciplinary Approaches to Realize Novel Catalytic Pathways to Energy Carriers, FWP 47319). Computational resources were provided by PNNL's Research Computing facility and the National Energy Research Scientific Computing Center (NERSC), which is a DOE Office of Science User Facility. Open access funding enabled and organized by Projekt DEAL. Funding Information: The research described in this paper is part of the Chemical Transformation Initiative at Pacific Northwest National Laboratory (PNNL), conducted under PNNL's Laboratory Directed Research and Development Program. D.M.C. and J.A.L. were supported by the U.S. Department of Energy (DOE), Office of Science, Office of Basic Energy Sciences, Division of Chemical Sciences, Geosciences and Biosciences (Transdisciplinary Approaches to Realize Novel Catalytic Pathways to Energy Carriers, FWP 47319). Computational resources were provided by PNNL's Research Computing facility and the National Energy Research Scientific Computing Center (NERSC), which is a DOE Office of Science User Facility. Open access funding enabled and organized by Projekt DEAL. Publisher Copyright: {\textcopyright} 2020 The Authors. Published by Wiley-VCH GmbH",
year = "2021",
month = jan,
day = "4",
doi = "10.1002/anie.202008178",
language = "English",
volume = "60",
pages = "290--296",
journal = "Angewandte Chemie - International Edition",
issn = "1433-7851",
publisher = "John Wiley and Sons Ltd",
number = "1",
}