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

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 and Andrey A. Fokin ()
Additional contact information
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

Nature, 2011, vol. 477, issue 7364, 308-311

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.

Date: 2011
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DOI: 10.1038/nature10367

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