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Quantum Tunneling Mediated Interfacial Synthesis of a Benzofuran Derivative
Author(s) -
Paintner Tobias,
Björk Jonas,
Du Ping,
Klyatskaya Svetlana,
Paszkiewicz Mateusz,
Hellwig Raphael,
Uphoff Martin,
Öner Murat A.,
Cuniberto Edoardo,
Deimel Peter S.,
Zhang YiQi,
Palma CarlosAndres,
Allegretti Francesco,
Ruben Mario,
Barth Johannes V.,
Klappenberger Florian
Publication year - 2019
Publication title -
angewandte chemie international edition
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 5.831
H-Index - 550
eISSN - 1521-3773
pISSN - 1433-7851
DOI - 10.1002/anie.201904030
Subject(s) - kinetic isotope effect , isomerization , density functional theory , chemistry , scanning tunneling microscope , photochemistry , chemical physics , quantum tunnelling , derivative (finance) , computational chemistry , benzofuran , deuterium , nanotechnology , stereochemistry , materials science , catalysis , organic chemistry , physics , atomic physics , optoelectronics , financial economics , economics
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.