Carbon-Carbon Bonds That Are Long And Strong | Chemical & Engineering News
Volume 89 Issue 38 | p. 28 | Concentrates
Issue Date: September 19, 2011

Carbon-Carbon Bonds That Are Long And Strong

Coupled diamondoids can take temperatures in excess of 200 °C without decomposing
Department: Science & Technology
Keywords: alkane, carbon-carbon bond, attractive dispersion interactions, London forces

A record has been set for the longest carbon-carbon bond in an alkane. A team led by Peter R. Schreiner of Germany’s Justus Liebig University, Giessen, and Andrey A. Fokin of Ukraine’s Kiev Polytechnic Institute report they have made an alkane with a C–C bond that’s 1.704 Å long (Nature, DOI: 10.1038/nature10367). Typical alkane C–C bonds measure 1.54 Å. The extra-long bond links two diamondoid structures (shown) and exhibits considerable strength, despite its length. Noticeable decomposition of the material occurs only at temperatures above 200 °C. Schreiner, Fokin, and coworkers attribute this stability to intramolecular attractive dispersion interactions—also known as London forces—between hydrogen atoms on the surface of the diamondoids near the elongated C–C bond. They used quantum chemical computations to show that this is the case. “Our findings have consequences for understanding rotational barriers and thermodynamic preferences of branched alkanes over linear alkanes and for the design of structures using attractive dispersion interactions,” the researchers note.

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