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Proton-Coupled Electron Transfer in Electrochemical Alanine Formation from Pyruvic Acid: Mechanism of Catalytic Reaction at the Interface between TiO2 (101) and Water

Cite this: J. Phys. Chem. C 2021, 125, 23, 12603–12613
Publication Date (Web):June 8, 2021
https://doi.org/10.1021/acs.jpcc.1c01304
Copyright © 2021 American Chemical Society

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    Abstract

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    We investigate the feasibility for conversion of biomass-derived raw materials into useful substances, which is important from the perspective of sustainable resource utilization. Our focus is on the electrochemical alanine formation from pyruvic acid. The reaction pathway was surveyed using first principles methods to propose a plausible mechanism for amino acid production from biomass-derived pyruvic acid at the cathode of TiO2. Our calculations show that amino acid formation from pyruvic acid involves seven elementary reactions mainly described by proton transfer. Our detailed spin density analysis for N–H bond formation revealed that the reaction is mediated by a proton-coupled electron transfer reaction, which sufficiently lowers the activation energy compared to that in simple hydrogen transfer. All proton transfer reactions occur via water bridges between the TiO2 surface oxygens and the reactant, suggesting that water is essential in the reaction mechanism.

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    • Imaginary frequencies of transition states, electronic energies of reactants, transition states, and products (PDF)

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    Cited By

    This article is cited by 5 publications.

    1. Benjing Xu, Jinhang Dai, Ziting Du, Fukun Li, Huan Liu, Xingxing Gu, Xingmin Wang, Ning Li, Jun Zhao. Catalytic conversion of biomass-derived compoUnds to various amino acids: status and perspectives. Frontiers of Chemical Science and Engineering 2023, 17 (7) , 817-829. https://doi.org/10.1007/s11705-022-2254-z
    2. Miho Yamauchi, Hikaru Saito, Toshiki Sugimoto, Shogo Mori, Susumu Saito. Sustainable organic synthesis promoted on titanium dioxide using coordinated water and renewable energies/resources. Coordination Chemistry Reviews 2022, 472 , 214773. https://doi.org/10.1016/j.ccr.2022.214773
    3. K. Fukutani, J. Yoshinobu, M. Yamauchi, T. Shima, S. Orimo. Hydrogenomics: Efficient and Selective Hydrogenation of Stable Molecules Utilizing Three Aspects of Hydrogen. Catalysis Letters 2022, 152 (6) , 1583-1597. https://doi.org/10.1007/s10562-021-03750-1
    4. Akihiko Anzai, Ming-Han Liu, Kenjiro Ura, Tomohiro G. Noguchi, Akina Yoshizawa, Kenichi Kato, Takeharu Sugiyama, Miho Yamauchi. Cu Modified TiO2 Catalyst for Electrochemical Reduction of Carbon Dioxide to Methane. Catalysts 2022, 12 (5) , 478. https://doi.org/10.3390/catal12050478
    5. Miho Isegawa, Takahiro Matsumoto, Seiji Ogo. H 2 activation by hydrogenase-inspired NiFe catalyst using frustrated Lewis pair: effect of buffer and halide ion in the heterolytic H–H bond cleavage. RSC Advances 2021, 11 (45) , 28420-28432. https://doi.org/10.1039/D1RA05928A

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