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Paintner T, Björk J, Du P, et al. Quantum Tunneling Mediated Interfacial Synthesis of a Benzofuran Derivative. Angew Chem Int Ed Engl. 2019;58(33):11285-11290doi: 10.1002/anie.201904030.
Paintner, T., Björk, J., Du, P., Klyatskaya, S., Paszkiewicz, M., Hellwig, R., Uphoff, M., Öner, M. A., Cuniberto, E., Deimel, P. S., Zhang, Y. Q., Palma, C. A., Allegretti, F., Ruben, M., Barth, J. V., & Klappenberger, F. (2019). Quantum Tunneling Mediated Interfacial Synthesis of a Benzofuran Derivative. Angewandte Chemie (International ed. in English), 58(33), 11285-11290. https://doi.org/10.1002/anie.201904030
Paintner, Tobias, et al. "Quantum Tunneling Mediated Interfacial Synthesis of a Benzofuran Derivative." Angewandte Chemie (International ed. in English) vol. 58,33 (2019): 11285-11290. doi: https://doi.org/10.1002/anie.201904030
Paintner T, Björk J, Du P, Klyatskaya S, Paszkiewicz M, Hellwig R, Uphoff M, Öner MA, Cuniberto E, Deimel PS, Zhang YQ, Palma CA, Allegretti F, Ruben M, Barth JV, Klappenberger F. Quantum Tunneling Mediated Interfacial Synthesis of a Benzofuran Derivative. Angew Chem Int Ed Engl. 2019 Aug 12;58(33):11285-11290. doi: 10.1002/anie.201904030. Epub 2019 Jul 04. PMID: 31120567.
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Angew Chem Int Ed Engl. 2019 Aug 12;58(33):11285-11290. doi: 10.1002/anie.201904030. Epub 2019 Jul 04.

Quantum Tunneling Mediated Interfacial Synthesis of a Benzofuran Derivative.

Angewandte Chemie (International ed. in English)

Tobias Paintner, Jonas Björk, Ping Du, Svetlana Klyatskaya, Mateusz Paszkiewicz, Raphael Hellwig, Martin Uphoff, Murat A Öner, Edoardo Cuniberto, Peter S Deimel, Yi-Qi Zhang, Carlos-Andres Palma, Francesco Allegretti, Mario Ruben, Johannes V Barth, Florian Klappenberger

Affiliations

  1. Physics Department E20, Technical University of Munich, 85748, Garching, Germany.
  2. Department of Physics, Chemistry and Biology, IFM, Linköping University, 58183, Linköping, Sweden.
  3. Institute of Nanotechnology, Karlsruhe Institute of Technology (KIT), Hermann-von-Helmholtz-Platz 1, 76344, Eggenstein-Leopoldshafen, Germany.
  4. Institute of Physics, Chinese Academy of Sciences, 100190, Beijing, P. R. China.
  5. Institute de Physique et Chimie de Matériaux (IPCMS), Université Strasbourg, 23 rue du Loess, BP 43, 67034, Strasbourg cedex 2, France.

PMID: 31120567 DOI: 10.1002/anie.201904030

Abstract

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.

© 2019 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim.

Keywords: X-ray spectroscopy; hydroalkoxylation; on-surface synthesis; quantum tunneling; scanning tunneling microscopy

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