Skip to main content
Log in

Effect of hydrostatic pressure, temperature, and solvent on the rate of the Diels–Alder reaction between 9,10-anthracenedimethanol and maleic anhydride

  • Chemical Kinetics and Catalysis
  • Published:
Russian Journal of Physical Chemistry A Aims and scope Submit manuscript

Abstract

The rate of the reaction between 9,10-anthracenedimethanol and maleic anhydride in 1,4-dioxane, acetonitrile, trichloromethane, and toluene is studied at 25, 35, 45°C in the pressure range of 1–1772 bar. The rate constants, enthalpies, entropies and activation volumes are determined. It is shown that the rate of reaction with 9,10-anthracenedimethanol is approximately one order of magnitude higher than with 9-anthracenemethanol.

This is a preview of subscription content, log in via an institution to check access.

Access this article

Price excludes VAT (USA)
Tax calculation will be finalised during checkout.

Instant access to the full article PDF.

Similar content being viewed by others

References

  1. D. C. Rideout and R. Breslow, J. Am. Chem. Soc. 102, 7816 (1980).

    Article  CAS  Google Scholar 

  2. R. Breslow, U. Maitra, and D. Rideout, Tetrahedron Lett. 24, 1901 (1983).

    Article  CAS  Google Scholar 

  3. R. Breslow and U. Maitra, Tetrahedron Lett. 25, 1239 (1984).

    Article  CAS  Google Scholar 

  4. R. Breslow and T. Guo, J. Am. Chem. Soc. 110, 5613 (1988).

    Article  CAS  Google Scholar 

  5. J. Light and R. Breslow, Tetrahedron Lett. 31, 2957 (1990).

    Article  CAS  Google Scholar 

  6. R. Breslow, Acc. Chem. Res. 24, 159 (1991).

    Article  CAS  Google Scholar 

  7. W. Blokzijl, M. J. Blandamer, and J. B. F. N. Engberts, J. Am. Chem. Soc. 113, 4241 (1991).

    Article  CAS  Google Scholar 

  8. W. Blokzijl and J. B. F. N. Engberts, J. Am. Chem. Soc. 114, 5440 (1992).

    Article  CAS  Google Scholar 

  9. S. Horiuchi, T. Murase, and M. Fujita, Asian J. Chem. 6, 1839 (2011).

    Article  CAS  Google Scholar 

  10. C.-J. Li, Chem. Rev. 93, 2023 (1993).

    Article  CAS  Google Scholar 

  11. X. Chen, J. F. Dobson, and C. L. Raston, Chem. Commun. 48, 3703 (2012).

    Article  CAS  Google Scholar 

  12. L. Yasmin, K. A. Stubbs, and C. L. Raston, Tetrahedron Lett. 55, 2246 (2014).

    Article  CAS  Google Scholar 

  13. S. Narayan, J. Muldoon, M. G. Finn, et al., Ang. Chem. Int. Ed. 44, 3275 (2005).

    Article  CAS  Google Scholar 

  14. J. E. Klijn and J. B. F. N. Engberts, Nature 435, 746 (2005).

    Article  CAS  Google Scholar 

  15. Y. Jung and R. A. Marcus, J. Am. Chem. Soc. 127, 5492 (2007).

    Article  Google Scholar 

  16. G. Desimoni, G. Faita, P. P. Righetti, and L. Toma, Tetrahedron 46, 7951 (1990).

    Article  CAS  Google Scholar 

  17. V. D. Kiselev, I. I. Shakirova, and A. I. Konovalov, Russ. Chem. Bull. 62, 285 (2013).

    Article  CAS  Google Scholar 

  18. V. D. Kiselev and A. I. Konovalov, J. Phys. Org. Chem. 22, 466 (2009).

    Article  CAS  Google Scholar 

  19. V. D. Kiselev and J. G. Miller, J. Am. Chem. Soc. 97, 4036 (1975).

    Article  CAS  Google Scholar 

  20. V. D. Kiselev, Int. J. Chem. Kinet. 45, 613 (2013).

    Article  CAS  Google Scholar 

  21. V. D. Kiselev, D. A. Kornilov, I. I. Lekomtseva, and A. I. Konovalov, Int. J. Chem. Kinet. 47, 289 (2015).

    Article  CAS  Google Scholar 

  22. V. D. Kiselev, E. A. Kashaeva, L. N. Potapova, et al., Izv. Akad. Nauk, Ser. Khim., No. 4360 (2016).

  23. J. Sauer, D. Lang, and A. Mielert, Angew. Chem. 74, 352 (1962).

    Article  CAS  Google Scholar 

  24. M. W. Miller, R. W. Amidon, and P. O. Tawney, J. Am. Chem. Soc. 77, 2845 (1955).

    Article  CAS  Google Scholar 

  25. M. H. Schwartz, S. M. Rosenfeld, C. I. Lee, et al., Tetrahedron Lett. 33, 6275 (1992).

    Article  CAS  Google Scholar 

  26. J. A. Riddick, W. B. Bunger, and T. K. Sakano, Organic Solvents, 4th ed. (Wiley, New York, Chichester, Brisbane, Toronto, Singapore, 1986).

    Google Scholar 

  27. V. D. Kiselev, A. V. Bolotov, A. P. Satonin, et al., J. Phys. Chem. B 112, 6674 (2008).

    Article  CAS  Google Scholar 

  28. V. D. Kiselev, I. I. Shakirova, D. A. Kornilov, E. A. Kashaeva, L. N. Potapova, and A. I. Konovalov, Russ. J. Phys. Chem. A 87, 160 (2013).

    Article  CAS  Google Scholar 

  29. V. D. Kiselev, D. A. Kornilov, E. A. Kashaeva, L. N. Potapova, D. B. Krivolapov, I. A. Litvinov, and A. I. Konovalov, Russ. J. Phys. Chem. A 88, 2073 (2014).

    Article  CAS  Google Scholar 

  30. D. A. Kornilov and V. D. Kiselev, J. Chem. Eng. Data 60, 3571 (2015).

    Article  CAS  Google Scholar 

Download references

Author information

Authors and Affiliations

Authors

Corresponding author

Correspondence to V. D. Kiselev.

Additional information

Original Russian Text © V.D. Kiselev, D.A. Kornilov, O.V. Anikin, L.I. Latypova, A.I. Konovalov, 2017, published in Zhurnal Fizicheskoi Khimii, 2017, Vol. 91, No. 3, pp. 446–449.

Rights and permissions

Reprints and permissions

About this article

Check for updates. Verify currency and authenticity via CrossMark

Cite this article

Kiselev, V.D., Kornilov, D.A., Anikin, O.V. et al. Effect of hydrostatic pressure, temperature, and solvent on the rate of the Diels–Alder reaction between 9,10-anthracenedimethanol and maleic anhydride. Russ. J. Phys. Chem. 91, 464–467 (2017). https://doi.org/10.1134/S0036024417030128

Download citation

  • Received:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1134/S0036024417030128

Keywords

Navigation