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Electrostatic and Charge-Induced Methane Activation by a Concerted Double C–H Bond Insertion

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    Electrostatic and Charge-Induced Methane Activation by a Concerted Double C–H Bond Insertion
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    † Institut für Chemie, Technische Universität Berlin, Straße des 17. Juni 135, 10623 Berlin, Germany
    ‡ Institute of Theoretical Chemistry, Jilin University, Changchun 130023, PR China
    § Institute of Chemistry and the Lise-Meitner-Minerva Center for Computational Quantum Chemistry, The Hebrew University of Jerusalem, 91904 Jerusalem, Israel
    *E-mail: [email protected]
    *E-mail: [email protected]
    *E-mail: [email protected]
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    Cite this: J. Am. Chem. Soc. 2017, 139, 4, 1684–1689
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    https://doi.org/10.1021/jacs.6b12514
    Published January 4, 2017
    Copyright © 2017 American Chemical Society
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    Abstract

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    A mechanistically unique, simultaneous activation of two C–H bonds of methane has been identified during the course of its reaction with the cationic copper carbide, [Cu–C]+. Detailed high-level quantum chemical calculations support the experimental findings obtained in the highly diluted gas phase using FT-ICR mass spectrometry. The behavior of [Cu–C]+/CH4 contrasts that of [Au–C]+/CH4, for which a stepwise bond-activation scenario prevails. An explanation for the distinct mechanistic differences of the two coinage metal complexes is given. It is demonstrated that the coupling of [Cu–C]+ with methane to form ethylene and Cu+ is modeled very well by the reaction of a carbon atom with methane mediated by an oriented external electric field of a positive point charge.

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    • Experimental and computational details, additional potential energy surfaces, energetic information, schematic molecular orbital diagrams, NBO-calculated charge and spin density mentioned in the main text, orbital components of 1[Cu–C]+ and 1[Au–C]+, plot of the influence of a point charge, plot of deformation energies vs the corresponding barriers, and Cartesian coordinates for key calculated species(PDF)

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    Cite this: J. Am. Chem. Soc. 2017, 139, 4, 1684–1689
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