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Quantum chemical study of ethynylfullerenes

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Abstract

DFT PBE0/cc-pVDZ method was applied to calculate the structural parameters of C60C(CCH)2, C60H2, C60H(t-Bu), C60HCCH, C60(CCH)2 molecules, and of the corresponding carbanions. The length of the carbon-carbon fullerene after the binding with the diethynylcarbene, atoms and/or radicals increases to 1.565, 1.577, 1.587, 1.591, 1.616 Å respectively, but in the relatively stable fulleride anions C60(t-Bu)− and C60CCH− this bond has a normal length of 1.525 Å. Acetylenide anions C60HCC−, C60(CCH)CC−, and C60C(CCH)CC− are weaker as Brønsted bases than the hypothetical dodecahedrane analogs, but stronger than C60(t-Bu)−, C60CCH−, and C60H− fulleride anions where the charge is localized on the fullerene core.

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Authors and Affiliations

  1. St. Petersburg State University, Universitetskii pr. 26, St. Petersburg, 198504, Russia

    M. V. Makarova, S. G. Semenov & R. R. Kostikov

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  1. M. V. Makarova
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  2. S. G. Semenov
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  3. R. R. Kostikov
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Correspondence to M. V. Makarova.

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Original Russian Text © M.V. Makarova, S.G. Semenov, R.R. Kostikov, 2015, published in Zhurnal Organicheskoi Khimii, 2015, Vol. 51, No. 2, pp. 283–286.

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Makarova, M.V., Semenov, S.G. & Kostikov, R.R. Quantum chemical study of ethynylfullerenes. Russ J Org Chem 51, 273–276 (2015). https://doi.org/10.1134/S1070428015020232

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  • DOI: https://doi.org/10.1134/S1070428015020232

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