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Quantum Tunneling Mediated Interfacial Synthesis of a Benzofuran Derivative
Tech Univ Munich, Germany.
Linköping University, Department of Physics, Chemistry and Biology, Thin Film Physics. Linköping University, Faculty of Science & Engineering.ORCID iD: 0000-0002-1345-0006
Karlsruhe Inst Technol, Germany.
Karlsruhe Inst Technol, Germany.
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2019 (English)In: Angewandte Chemie International Edition, ISSN 1433-7851, E-ISSN 1521-3773, Vol. 58, no 33, p. 11285-11290Article in journal (Refereed) Published
Abstract [en]

Reaction pathways involving quantum tunneling of protons are fundamental to chemistry and biology. They are responsible for essential aspects of interstellar synthesis, the degradation and isomerization of compounds, enzymatic activity, and protein dynamics. On-surface conditions have been demonstrated to open alternative routes for organic synthesis, often with intricate transformations not accessible in solution. Here, we investigate a hydroalkoxylation reaction of a molecular species adsorbed on a Ag(111) surface by scanning tunneling microscopy complemented by X-ray electron spectroscopy and density functional theory. The closure of the furan ring proceeds at low temperature (down to 150 K) and without detectable side reactions. We unravel a proton-tunneling-mediated pathway theoretically and confirm experimentally its dominant contribution through the kinetic isotope effect with the deuterated derivative.

Place, publisher, year, edition, pages
WILEY-V C H VERLAG GMBH , 2019. Vol. 58, no 33, p. 11285-11290
Keywords [en]
hydroalkoxylation; on-surface synthesis; quantum tunneling; scanning tunneling microscopy; X-ray spectroscopy
National Category
Organic Chemistry
Identifiers
URN: urn:nbn:se:liu:diva-161200DOI: 10.1002/anie.201904030ISI: 000478735900014PubMedID: 31120567OAI: oai:DiVA.org:liu-161200DiVA, id: diva2:1365679
Note

Funding Agencies|Deutsche ForschungsgemeinschaftGerman Research Foundation (DFG) [Munich Center for Advanced Photonics, TUM Institute of Advanced Studies, priority program TR88 3Met, priority program 1459, KL 2294/6-1, KL 2294/3-1]; European Research CouncilEuropean Research Council (ERC) [MolArt (no. 247299)]; Swedish Government Strategic Research Area in Materials Science on Functional Materials [SFO-Mat-LiU No 2009 00971]

Available from: 2019-10-25 Created: 2019-10-25 Last updated: 2019-10-25

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