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Organic chemistry

Stabilizers cause instability

Nature volume 481, pages 274–275 (2012)Cite this article

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Any chemist will tell you that amide compounds are renowned for their stability, yet a family of amides has been discovered that is surprisingly unstable. The cause of this phenomenon is even more surprising.

Some molecules are stable under all kinds of conditions; others are so unstable that they'll react with almost anything. Amides, the class of compounds that includes proteins and nylon, are usually stable molecules. Strong acid or alkali is needed to break them down — nylon fabrics are highly resistant to chemical damage, and dietary proteins can be digested only by the acidity of the stomach coupled with a battery of enzymes. Writing in Angewandte Chemie, Hutchby et al.1 report a group of amides that turns this typical character on its head. These compounds share structural characteristics with the least reactive amides of all, yet a remarkable mechanistic quirk means they exhibit reactivity that is usually associated with unstable reagents.

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Figure 1: Amide reactivity.

References

  1. Hutchby, M. et al. Angew. Chem. Int. Edn 51, 548–551 (2012).

    CAS  Article  Google Scholar 

  2. Snieckus, V. Chem. Rev. 90, 879–933 (1990).

    CAS  Article  Google Scholar 

  3. Clayden, J., Foricher, Y. J. Y. & Lam, H. K. Chem. Commun. 2138–2139 (2002).

  4. Clayden, J., Foricher, Y. J. Y. & Lam, H. K. Eur. J. Org. Chem. 3558–3565 (2002).

  5. Clayden, J. & Moran, W. J. Angew. Chem. Int. Edn 45, 7118–7120 (2006).

    CAS  Article  Google Scholar 

  6. Szostak, M. & Aubé, J. Org. Biomol. Chem. 9, 27–35 (2011).

    CAS  Article  Google Scholar 

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  1. Jonathan Clayden is in the School of Chemistry, University of Manchester, Manchester M13 9PL, UK.,

    Jonathan Clayden

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  1. Jonathan Clayden
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Correspondence to Jonathan Clayden.

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Clayden, J. Stabilizers cause instability. Nature 481, 274–275 (2012). https://doi.org/10.1038/481274a

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