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The 1,3 dipolar cycloaddition of azomethine ylides to graphene, single wall carbon nanotubes, and C60

Authors

  • Pablo A. Denis,

    Corresponding author
    1. Computational Nanotechnology, DETEMA, Facultad de Química, UDELAR, CC 1157, Montevideo 11800, Uruguay
    • Computational Nanotechnology, DETEMA, Facultad de Química, UDELAR, CC 1157, Montevideo 11800, Uruguay
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  • Federico Iribarne

    1. Laboratorio de Bioinformática y Farmacología Molecular, DETEMA, Facultad de Química, UDELAR, CC 1157, Montevideo 11800, Uruguay
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Abstract

Herein, we perform a comparative study on the addition of azomethine ylides to graphene, carbon nanotubes, C60, ethene, pyrene and a C48H18 hydrocarbon. The calculated binding energies and free energy corrections suggest that the addition of azomethine ylide to perfect graphene is not spontaneous (ΔG > 0). However, the presence of Stones–Wales defects significantly increases reactivity: the binding energy between SW-defective graphene and the azomethine ylide is 0.83 eV, close to that determined for a (5,5) SWCNT. The electronic properties of the sheet are not modified by the 1,3 cycloaddition. The binding energies determined for the addition of an azomethine ylide to a (5,5) SWCNT are significantly lower than previously reported. © 2009 Wiley Periodicals, Inc. Int J Quantum Chem, 2010

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