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Discovery of a stable single-electron covalent bond between two carbon atoms validates a century-old theory

Scientists discover a single-electron bond in a carbon-based compound
Using an X-ray diffractor to study the sigma bond. Credit: Yusuke Ishigaki

Covalent bonds, in which two atoms are bound together by sharing a pair of electrons, form the scaffolding that underpins the majority of organic compounds. In 1931, the Nobel Laureate Linus Pauling suggested that covalent bonds made from just a single, unpaired electron could exist, but these single-electron bonds would likely be much weaker than a standard covalent bond involving a pair of electrons.

Since then, bonds have been observed, but never in carbon or hydrogen—the hunt for one-electron bonds shared between carbon atoms has stymied scientists.

Now, a team of researchers from Hokkaido University has isolated a compound in which a single electron is shared between two carbon atoms in a remarkably stable covalent bond, known as a sigma bond. Their findings are in the journal Nature.

"Elucidating the nature of single-electron sigma-bonds between two carbon atoms is essential to gain a deeper understanding of chemical-bonding theories and would provide further insights into ," explains Professor Yusuke Ishigaki, of the Department of Chemistry at Hokkaido University, who co-authored the study.

Scientists discover a single-electron bond in a carbon-based compound
Structure of the compound highlighting the C–C sigma bond (red). Credit: Takuya Shimajiri, et al. Nature. September 25, 2024

The single-electron bond was formed by subjecting a derivative of hexaphenylethane, which contains an extremely stretched out paired-electron covalent bond between two carbon atoms, to an oxidation reaction in the presence of iodine. The reaction produced dark violet-colored crystals of an iodine salt.

The team used X-ray diffraction analysis to study the crystals and found that the carbon atoms in them were extremely close together, suggesting the presence of single-electron between carbon atoms. They were then able to confirm this using a form of chemical analysis called Raman spectroscopy.

"These results thus constitute the first piece of experimental evidence for a carbon-carbon single-electron covalent bond, which can be expected to pave the way for further developments of the chemistry of this scarcely-explored type of bonding," Takuya Shimajiri, the lead author of the paper and now at the University of Tokyo, says.

More information: Takuya Shimajiri et al, Direct evidence for a carbon–carbon one-electron σ-bond, Nature (2024). .

Journal information: Nature

Provided by Hokkaido University

Citation: Discovery of a stable single-electron covalent bond between two carbon atoms validates a century-old theory (2024, September 25) retrieved 23 May 2025 from /news/2024-09-discovery-stable-electron-covalent-bond.html
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