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Hydroxymethyl hydroperoxide and bis(hydroxymethyl) peroxide from gas-phase ozonolysis of naturally occurring alkenes

Nature volume 316, pages 535–536 (1985)Cite this article

A Corrigendum to this article was published on 01 November 1985

Abstract

Ozonolysis is one of the main pathways for degradation of alkenes in the atmosphere, where the reaction is associated with smog formation1 and the haze that often occurs over forests2,3. In recent decades, ground-level ozone concentrations have greatly increased4,5. The possibility of significant damage to plants by ozone and its products has consequently been raised in discussions of ‘waldsterben’, the large-scale dying of trees in northern Europe and North America6–9. With particular regard to the formation of peroxides, we have used 13C- nuclear magnetic resonance (NMR) to investigate the water-soluble products of the gas-phase ozonolysis of isoprene and several terpenes, which are emitted into the atmosphere in large quantities (108–109 tonnes yr−1 globally) by trees3,10,11. All these alkenes yield bis(hydroxymethyl)peroxide (BHMP; HOCH2OOCH2OH). The apparent precursor of BHMP is hydroxymethyl hydroperoxide (HMP; HOCH2OOH), which results from addition of water to the ozonolysis intermediate. As both HMP and BHMP have various toxic effects on plant cells and enzymes12–14, we point out here an indirect way by which ozone may adversely affect forests.

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References

  1. Pitts, J. N. Jr & Finlayson, B. J. Angew. Chem. 87, 18–33 (1975).

    Article  CAS  Google Scholar 

  2. Went, F. W. Proc. natn. Acad. Sci. U.S.A. 46, 212–221 (1960).

    Article  ADS  CAS  Google Scholar 

  3. Graedel, T. E. Rev. geophys. Space Phys. 17, 937–947 (1979).

    Article  ADS  CAS  Google Scholar 

  4. Warmbt, W. Z. Met. 29, 24–31 (1979).

    ADS  Google Scholar 

  5. Penkett, S. A. Nature 311, 14–15 (1984).

    Article  ADS  Google Scholar 

  6. Frank, H. Nachr. Chem. Tech. 32, 298–305 (1984).

    Article  CAS  Google Scholar 

  7. Kohlmaier, G. H., Bröhl, H. & Sirè, E. O. Allg. Forst Jagdztg. 154, 170–174 (1983).

    CAS  Google Scholar 

  8. Schöpfer, W. & Hradetzky, J. Forstwiss. Zentbl. 103, 231–246 (1984).

    Article  Google Scholar 

  9. Prinz, B., Krause, G. H. M. & Stratmann, H. Landesanstalt fur Immissionsschutz des Landes Nordrhein-Westfalen, Essen, Bericht 28(1982).

  10. Rasmussen, R. A. J. Air. Poll. Contr. Ass. 22, 537–543 (1972).

    Article  CAS  Google Scholar 

  11. Zimmerman, P. R., Chatfield, R. B., Fishman, J., Crutzen, P. J. & Hanst, P. L. Geophys. Res. Lett. 5, 679–682 (1978).

    Article  ADS  CAS  Google Scholar 

  12. Keusch, F. Ber. schweiz. hot. Ges. 81, 180–272 (1971).

    Google Scholar 

  13. Marklund, S. Biochim. biophys. Acta 258, 9–16 (1972).

    Article  CAS  Google Scholar 

  14. Marklund, S. Archs Biochem. Biophys. 154, 614–622 (1973).

    Article  CAS  Google Scholar 

  15. Rieche, A. & Meister, R. Chem. Ber. 68, 1468–1472 (1935).

    Article  Google Scholar 

  16. Rieche, A. & Meister, R. Chem. Ber. 66, 718–727 (1933).

    Article  Google Scholar 

  17. Martinez, R. I., Herron, J. T. & Huie, R. E. J. Am. chem. Soc. 103, 3807–3820 (1981).

    Article  CAS  Google Scholar 

  18. Bailey, P. S. Ozonation in Organic Chemistry Vol. 1 (Academic, New York, 1982).

    Chapter  Google Scholar 

  19. Cox, R. A. & Penkett, S. A. JCS Faraday Trans. 1 68, 1735–1753 (1972).

    Article  CAS  Google Scholar 

  20. Su, F., Calvert, J. G. & Shaw, J. H. J. phys. Chem. 84, 239–246 (1980).

    Article  CAS  Google Scholar 

  21. Story, P. R. & Burgess, J. R. J. Am. chem. Soc. 89, 5726–5727 (1967).

    Article  CAS  Google Scholar 

  22. Wadt, W. R. & Goddard, W. A. III J. Am. chem. Soc. 97, 3004–3021 (1975).

    Article  CAS  Google Scholar 

  23. Lloyd, A. C., Atkinson, R., Lurmann, F. W. & Nitta, B. Atmos. Envir. 17, 1931–1950 (1983).

    Article  CAS  Google Scholar 

  24. Arora, P. K. & Vohra, K. G. Chem. Phys. Lett. 96, 161–166 (1983).

    Article  ADS  CAS  Google Scholar 

  25. Briner, E. & Schnorf, P. Helv. chim. Acta 12, 154–181 (1929).

    Article  CAS  Google Scholar 

  26. Briner, E. & Meier, R. Helv. chim. Acta 12, 529–553 (1929).

    Article  CAS  Google Scholar 

  27. Herron, J. T., Martinez, R. I. & Huie, R. E. Int. J. chem. Kin. 14, 201–224 (1982).

    Article  CAS  Google Scholar 

  28. Sobels, F. H. Nature 177, 979–982 (1956).

    Article  ADS  CAS  Google Scholar 

  29. Dickey, F. H., Cleland, G. H. & Lotz, C. Proc. natn. Acad. Sci. U.S.A. 35, 581–586 (1949).

    Article  ADS  CAS  Google Scholar 

  30. Weitzel, G., Buddecke, E. & Schneider, F. Hoppe-Seylers Z. physiol. Chem. 323, 211–235 (1961).

    Article  CAS  Google Scholar 

  31. Weitzel, G., Buddecke, E., Schneider, F. & Pfeil, H. Hoppe-Seylers Z. physiol. Chem. 325, 65–90 (1961).

    Article  CAS  Google Scholar 

  32. Loveless, A. Nature 167, 338–342 (1951).

    Article  ADS  CAS  Google Scholar 

  33. Marklund, S. Acta chem. Scand. 25, 3517–3531 (1971).

    Article  CAS  Google Scholar 

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Authors and Affiliations

  1. Institut für Ökologische Chemie der Gesellschaft für Strahlen- und Umweltforschung mbH, München, D-8050, Freising-Weihenstephan, FRG

    S. Gäb, E. Hellpointner, W. V. Turner & F. Koŕte

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  1. S. Gäb
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Gäb, S., Hellpointner, E., Turner, W. et al. Hydroxymethyl hydroperoxide and bis(hydroxymethyl) peroxide from gas-phase ozonolysis of naturally occurring alkenes. Nature 316, 535–536 (1985). https://doi.org/10.1038/316535a0

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