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Chemistry

On the threshold of stability

Nature volume 412, pages 598–601 (2001)Cite this article

Carbenes are short-lived compounds containing a highly reactive carbon atom, which makes them difficult to study. A stabilized derivative may lead to new magnetic materials.

Carbon usually has four atoms or groups bonded to it. Many reactions in organic chemistry involve breaking one of these covalent bonds, so chemists are naturally interested in the reactive and unstable species of carbon that fleetingly form during these reactions. The most common carbon intermediates are trivalent species, which form only three bonds. Covalent bonds form when adjacent atoms share two electrons, so many trivalent carbon compounds have one unpaired electron. Intermediates containing a divalent carbon atom that forms only two covalent bonds, such as CH2, are even more reactive than their trivalent cousins. Such species, called carbenes, have two non-bonding electrons on the same carbon atom. Despite the importance of carbenes to organic synthesis, their short microsecond lifetimes make them difficult to study. On page 626 of this issue, Tomioka and colleagues1 report the successful preparation of the first triplet carbene with a long lifetime — almost 20 minutes at room temperature. A truly stable version of this particular carbene could lead to useful magnetic materials.

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Figure 1: Stabilization of carbenes.
Figure 2: Carbenes that can almost be bottled.

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  1. Department of Chemistry and Chemical Biology, Rutgers University, 610 Taylor Road, New Brunswick, 08854-8087, New Jersey, USA

    Heinz D. Roth

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  1. Heinz D. Roth
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Correspondence to Heinz D. Roth.

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Roth, H. On the threshold of stability. Nature 412, 598–601 (2001). https://doi.org/10.1038/35088170

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