Title: Electrochemical Synthesis of Glycine from Oxalic Acid and Nitrate
Abstract: Angewandte Chemie International EditionVolume 60, Issue 40 p. 21943-21951 Research Article Electrochemical Synthesis of Glycine from Oxalic Acid and Nitrate Jeong Eun Kim, Jeong Eun Kim Department of Materials Science and Engineering, Seoul National University, Gwanak-ro, Gwanak-gu, Seoul, 08826 Republic of Korea These authors contributed equally to this work.Search for more papers by this authorJun Ho Jang, Jun Ho Jang Department of Materials Science and Engineering, Seoul National University, Gwanak-ro, Gwanak-gu, Seoul, 08826 Republic of Korea These authors contributed equally to this work.Search for more papers by this authorKyu Min Lee, Kyu Min Lee Department of Materials Science and Engineering, Seoul National University, Gwanak-ro, Gwanak-gu, Seoul, 08826 Republic of KoreaSearch for more papers by this authorMani Balamurugan, Mani Balamurugan Department of Materials Science and Engineering, Seoul National University, Gwanak-ro, Gwanak-gu, Seoul, 08826 Republic of KoreaSearch for more papers by this authorYoung In Jo, Young In Jo Department of Materials Science and Engineering, Seoul National University, Gwanak-ro, Gwanak-gu, Seoul, 08826 Republic of KoreaSearch for more papers by this authorMoo Young Lee, Moo Young Lee Department of Materials Science and Engineering, Seoul National University, Gwanak-ro, Gwanak-gu, Seoul, 08826 Republic of KoreaSearch for more papers by this authorSeungwoo Choi, Seungwoo Choi Department of Materials Science and Engineering, Seoul National University, Gwanak-ro, Gwanak-gu, Seoul, 08826 Republic of KoreaSearch for more papers by this authorSang Won Im, Sang Won Im Department of Materials Science and Engineering, Seoul National University, Gwanak-ro, Gwanak-gu, Seoul, 08826 Republic of KoreaSearch for more papers by this authorProf. Ki Tae Nam, Corresponding Author Prof. Ki Tae Nam [email protected] orcid.org/0000-0001-6353-8877 Department of Materials Science and Engineering, Seoul National University, Gwanak-ro, Gwanak-gu, Seoul, 08826 Republic of KoreaSearch for more papers by this author Jeong Eun Kim, Jeong Eun Kim Department of Materials Science and Engineering, Seoul National University, Gwanak-ro, Gwanak-gu, Seoul, 08826 Republic of Korea These authors contributed equally to this work.Search for more papers by this authorJun Ho Jang, Jun Ho Jang Department of Materials Science and Engineering, Seoul National University, Gwanak-ro, Gwanak-gu, Seoul, 08826 Republic of Korea These authors contributed equally to this work.Search for more papers by this authorKyu Min Lee, Kyu Min Lee Department of Materials Science and Engineering, Seoul National University, Gwanak-ro, Gwanak-gu, Seoul, 08826 Republic of KoreaSearch for more papers by this authorMani Balamurugan, Mani Balamurugan Department of Materials Science and Engineering, Seoul National University, Gwanak-ro, Gwanak-gu, Seoul, 08826 Republic of KoreaSearch for more papers by this authorYoung In Jo, Young In Jo Department of Materials Science and Engineering, Seoul National University, Gwanak-ro, Gwanak-gu, Seoul, 08826 Republic of KoreaSearch for more papers by this authorMoo Young Lee, Moo Young Lee Department of Materials Science and Engineering, Seoul National University, Gwanak-ro, Gwanak-gu, Seoul, 08826 Republic of KoreaSearch for more papers by this authorSeungwoo Choi, Seungwoo Choi Department of Materials Science and Engineering, Seoul National University, Gwanak-ro, Gwanak-gu, Seoul, 08826 Republic of KoreaSearch for more papers by this authorSang Won Im, Sang Won Im Department of Materials Science and Engineering, Seoul National University, Gwanak-ro, Gwanak-gu, Seoul, 08826 Republic of KoreaSearch for more papers by this authorProf. Ki Tae Nam, Corresponding Author Prof. Ki Tae Nam [email protected] orcid.org/0000-0001-6353-8877 Department of Materials Science and Engineering, Seoul National University, Gwanak-ro, Gwanak-gu, Seoul, 08826 Republic of KoreaSearch for more papers by this author First published: 29 July 2021 https://doi.org/10.1002/anie.202108352Citations: 2 Read the full textAboutPDF ToolsRequest permissionExport citationAdd to favoritesTrack citation ShareShare Give accessShare full text accessShare full-text accessPlease review our Terms and Conditions of Use and check box below to share full-text version of article.I have read and accept the Wiley Online Library Terms and Conditions of UseShareable LinkUse the link below to share a full-text version of this article with your friends and colleagues. Learn more.Copy URL Share a linkShare onFacebookTwitterLinked InRedditWechat Abstract By electrochemical method, stable oxalic acid and nitrate substrates were coupled into an amino acid, glycine. Insertion of electrons resulted in their conversion into nucleophile and electrophile, respectively, which led to C=N bond formation between them, as well as the conversion of the reversible C=N double bond to a stable C−N single bond. Abstract In manufacturing C−N bond-containing compounds, it is an important challenge to alternate the conventional methodologies that utilize reactive substrates, toxic reagents, and organic solvents. In this study, we developed an electrochemical method to synthesize a C−N bond-containing molecule avoiding the use of cyanides and amines by harnessing nitrate (NO3−) as a nitrogen source in an aqueous electrolyte. In addition, we utilized oxalic acid as a carbon source, which can be obtained from electrochemical conversion of CO2. Thus, our approach can provide a route for the utilization of anthropogenic CO2 and nitrate wastes, which cause serious environmental problems including global warming and eutrophication. Interestingly, the coreduction of oxalic acid and nitrate generated reactive intermediates, which led to C−N bond formation followed by further reduction to an amino acid, namely, glycine. By carefully controlling this multireduction process with a fabricated Cu–Hg electrode, we demonstrated the efficient production of glycine with a faradaic efficiency (F.E.) of up to 43.1 % at −1.4 V vs. Ag/AgCl (current density≈90 mA cm−2). Citing Literature Supporting Information As a service to our authors and readers, this journal provides supporting information supplied by the authors. Such materials are peer reviewed and may be re-organized for online delivery, but are not copy-edited or typeset. Technical support issues arising from supporting information (other than missing files) should be addressed to the authors. Filename Description anie202108352-sup-0001-misc_information.pdf950.8 KB Supporting Information Please note: The publisher is not responsible for the content or functionality of any supporting information supplied by the authors. Any queries (other than missing content) should be directed to the corresponding author for the article. Volume60, Issue40September 27, 2021Pages 21943-21951 RelatedInformation
Publication Year: 2021
Publication Date: 2021-08-26
Language: en
Type: article
Indexed In: ['crossref', 'pubmed']
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Cited By Count: 68
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