Journal article

Authors list: Schreiner, PR; Chernish, LV; Gunchenko, PA; Tikhonchuk, EY; Hausmann, H; Serafin, M; Schlecht, S; Dahl, JEP; Carlson, RMK; Fokin, AA

Publication year: 2011

Pages: 308-311

Journal: Nature

Volume number: 477

Issue number: 7364

ISSN: 0028-0836

DOI Link: https://doi.org/10.1038/nature10367

Publisher: Nature Research

Abstract: 

Steric effects in chemistry are a consequence of the space required to
accommodate the atoms and groups within a molecule, and are often
thought to be dominated by repulsive forces arising from overlapping
electron densities (Pauli repulsion). An appreciation of attractive
interactions such as van der Waals forces (which include London
dispersion forces) is necessary to understand chemical bonding and
reactivity fully. This is evident from, for example, the strongly
debated origin of the higher stability of branched alkanes relative to
linear alkanes^1,2 and the possibility of constructing hydrocarbons with extraordinarily long C–C single bonds through steric crowding³. Although empirical bond distance/bond strength relationships have been established for C–C bonds⁴ (longer C–C bonds have smaller bond dissociation energies), these have no present theoretical basis⁵. Nevertheless, these empirical considerations are fundamental to structural and energetic evaluations in chemistry^6,7, as summarized by Pauling⁸ as early as 1960 and confirmed more recently⁴.
Here we report the preparation of hydrocarbons with extremely long C–C
bonds (up to 1.704 Å), the longest such bonds observed so far in
alkanes. The prepared compounds are unexpectedly stable—noticeable
decomposition occurs only above 200 °C. We prepared the alkanes by
coupling nanometre-sized, diamond-like, highly rigid structures known as
diamondoids⁹.
The extraordinary stability of the coupling products is due to overall
attractive dispersion interactions between the intramolecular H•••H
contact surfaces, as is evident from density functional theory
computations with¹⁰ and without inclusion of dispersion corrections.

Harvard Citation style: Schreiner, P., Chernish, L., Gunchenko, P., Tikhonchuk, E., Hausmann, H., Serafin, M., et al. (2011) Overcoming lability of extremely long alkane carbon–carbon bonds through dispersion forces, Nature, 477(7364), pp. 308-311. https://doi.org/10.1038/nature10367

APA Citation style: Schreiner, P., Chernish, L., Gunchenko, P., Tikhonchuk, E., Hausmann, H., Serafin, M., Schlecht, S., Dahl, J., Carlson, R., & Fokin, A. (2011). Overcoming lability of extremely long alkane carbon–carbon bonds through dispersion forces. Nature. 477(7364), 308-311. https://doi.org/10.1038/nature10367