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Overcoming lability of extremely long alkane carbon–carbon bonds through dispersion forces

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  • Peter R. Schreiner

    (Institut für Organische Chemie der Justus-Liebig-Universität, Heinrich-Buff-Ring 58, D-35392 Giessen, Germany)

  • Lesya V. Chernish

    (Kiev Polytechnic Institute, 37 Pobeda Avenue, Kiev 03056, Ukraine)

  • Pavel A. Gunchenko

    (Kiev Polytechnic Institute, 37 Pobeda Avenue, Kiev 03056, Ukraine)

  • Evgeniya Yu. Tikhonchuk

    (Kiev Polytechnic Institute, 37 Pobeda Avenue, Kiev 03056, Ukraine)

  • Heike Hausmann

    (Institut für Organische Chemie der Justus-Liebig-Universität, Heinrich-Buff-Ring 58, D-35392 Giessen, Germany)

  • Michael Serafin

    (Institut für Anorganische Chemie der Justus-Liebig-Universität, Heinrich-Buff-Ring 58, D-35392 Giessen, Germany)

  • Sabine Schlecht

    (Institut für Anorganische Chemie der Justus-Liebig-Universität, Heinrich-Buff-Ring 58, D-35392 Giessen, Germany)

  • Jeremy E. P. Dahl

    (Stanford University, Stanford Institute for Materials & Energy Science, 476 Lomita Mall, Stanford, California 94305, USA)

  • Robert M. K. Carlson

    (Stanford University, Stanford Institute for Materials & Energy Science, 476 Lomita Mall, Stanford, California 94305, USA)

  • Andrey A. Fokin

    (Institut für Organische Chemie der Justus-Liebig-Universität, Heinrich-Buff-Ring 58, D-35392 Giessen, Germany
    Kiev Polytechnic Institute, 37 Pobeda Avenue, Kiev 03056, Ukraine)

Abstract

Strength at length in carbon–carbon bonds The synthesis of alkane hydrocarbons containing extremely long carbon–carbon (C–C) bonds, the longest observed in alkanes to date, is reported. Long C–C bonds are usually weaker than short ones, but these new alkanes are surprisingly stable, with decomposition occurring only above 200 °C. Quantum mechanical calculations show that, remarkably, the compounds are stabilized by attractive interactions between bulky groups at either end of the long C–C bonds. The stabilizing interactions observed in these compounds could prove useful in the development of new materials that utilize attractive dispersion interactions.

Suggested Citation

  • Peter R. Schreiner & Lesya V. Chernish & Pavel A. Gunchenko & Evgeniya Yu. Tikhonchuk & Heike Hausmann & Michael Serafin & Sabine Schlecht & Jeremy E. P. Dahl & Robert M. K. Carlson & Andrey A. Fokin, 2011. "Overcoming lability of extremely long alkane carbon–carbon bonds through dispersion forces," Nature, Nature, vol. 477(7364), pages 308-311, September.
    • Handle: RePEc:nat:nature:v:477:y:2011:i:7364:d:10.1038_nature10367
    DOI: 10.1038/nature10367
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