Skip to main content

Thank you for visiting You are using a browser version with limited support for CSS. To obtain the best experience, we recommend you use a more up to date browser (or turn off compatibility mode in Internet Explorer). In the meantime, to ensure continued support, we are displaying the site without styles and JavaScript.

Reactive intermediates

Radicals with multiple personalities

A combined theoretical and experimental approach has revealed that radicals can be significantly stabilized by the presence of a remote anionic site in the same molecule. This finding has implications for understanding and potentially controlling the reactivity of these important reactive intermediates.

This is a preview of subscription content, access via your institution

Access options

Rent or buy this article

Prices vary by article type



Prices may be subject to local taxes which are calculated during checkout

Figure 1: Switching radical stability.


  1. Tomazela, D. M., Sabino, A. A., Sparrapan, R., Gozzo, F. C. & Eberlin, M. N. J. Am. Soc. Mass Spectrom. 17, 1014–1022 (2006).

    Article  CAS  Google Scholar 

  2. Stirk, K. M., Kiminkinen, L. K. M. & Kenttamaa, H. I. Chem. Rev. 92, 1649–1665 (1992).

    Article  CAS  Google Scholar 

  3. Tanko, J. M. & Phillips, J. P. J. Am. Chem. Soc. 121, 6078–80 (1999).

    Article  CAS  Google Scholar 

  4. Yang, J., Felton, G. A. N., Bauld, N. L. & Krische, M. J. J. Am. Chem. Soc. 126, 1634–1635 (2004).

    Article  CAS  Google Scholar 

  5. Giese, B. Acc. Chem. Res. 33 631–636 (2000).

    Article  CAS  Google Scholar 

  6. George, P., Siegbahn, P. E. M., Glusker, J. P. & Bock, C. W. J. Phys. Chem. B 103, 7531–7541 (1999).

    Article  CAS  Google Scholar 

  7. Sugawara, T., Komatsu, H. & Suzuki, K. Chem. Soc. Rev. 40, 3105–3118 (2011).

    Article  CAS  Google Scholar 

  8. Grin'ova, G., Marshall, D. L., Blanskby, S. J. & Coote, M. L. Nature Chem. 5, 474–481 10.1038/nchem.1625(2013).

    Article  CAS  Google Scholar 

  9. Verhoeven, J. W. & Pasman, P. Tetrahedron 37, 943–947 (1981).

    Article  CAS  Google Scholar 

  10. Hawker, C. J., Bosman, A. W. & Harth, E. Chem. Rev. 101, 3661–3688 (2001).

    Article  CAS  Google Scholar 

Download references

Author information

Authors and Affiliations


Corresponding author

Correspondence to Malcolm D. E. Forbes.

Rights and permissions

Reprints and Permissions

About this article

Cite this article

Forbes, M. Radicals with multiple personalities. Nature Chem 5, 447–449 (2013).

Download citation

  • Published:

  • Issue Date:

  • DOI:


Quick links

Nature Briefing

Sign up for the Nature Briefing newsletter — what matters in science, free to your inbox daily.

Get the most important science stories of the day, free in your inbox. Sign up for Nature Briefing