Abiotic Formation of an Amide Bond via Surface-Supported Direct Carboxyl-Amine CouplingVisa övriga samt affilieringar
2022 (Engelska)Ingår i: Angewandte Chemie International Edition, ISSN 1433-7851, E-ISSN 1521-3773, Vol. 61, nr 5, artikel-id e202113590Artikel i tidskrift (Refereegranskat) Published
Abstract [en]
Amide bond formation is one of the most important reactions in biochemistry, notably being of crucial importance for the origin of life. Herein, we combine scanning tunneling microscopy and X-ray photoelectron spectroscopy studies to provide evidence for thermally activated abiotic formation of amide bonds between adsorbed precursors through direct carboxyl-amine coupling under ultrahigh-vacuum conditions by means of on-surface synthesis. Complementary insights from temperature-programmed desorption measurements and density functional theory calculations reveal the competition between cross-coupling amide formation and decarboxylation reactions on the Au(111) surface. Furthermore, we demonstrate the critical influence of the employed metal support: whereas on Au(111) the coupling readily occurs, different reaction scenarios prevail on Ag(111) and Cu(111). The systematic experiments signal that archetypical bio-related molecules can be abiotically synthesized in clean environments without water or oxygen.
Ort, förlag, år, upplaga, sidor
WILEY-V C H VERLAG GMBH , 2022. Vol. 61, nr 5, artikel-id e202113590
Nyckelord [en]
amides; decarboxylation; density functional theory; on-surface synthesis; scanning tunneling microscopy
Nationell ämneskategori
Oorganisk kemi
Identifikatorer
URN: urn:nbn:se:liu:diva-182223DOI: 10.1002/anie.202113590ISI: 000730213800001PubMedID: 34708485OAI: oai:DiVA.org:liu-182223DiVA, id: diva2:1626783
Anmärkning
Funding Agencies|National Major State Basic Research Development Program of ChinaNational Basic Research Program of China [2017YFA0205000, 2017YFA0205002]; National Science Foundation of ChinaNational Natural Science Foundation of China (NSFC) [21790053, 51821002, 22072102, 21872099]; German Research Foundation (DFG) through the Excellence Cluster e-conversionGerman Research Foundation (DFG); Swedish Government Strategic Research Area in Materials Science on Functional Materials at Linkoping University [2009 00971]; TUM International Graduate School of Science and Engineering (IGSSE) via the DFG [GSC 81]; Alexander von Humboldt-FoundationAlexander von Humboldt Foundation; Swedish Research CouncilSwedish Research CouncilEuropean Commission
2022-01-122022-01-122023-04-06Bibliografiskt granskad