Skip to main content
SpringerLink
Log in

The Catalytic Effect of Hydrogen Bonding Upon Epoxide Ring-Opening

  • Conference paper
Catalysis in Chemistry and Biochemistry Theory and Experiment

Part of the book series: The Jerusalem Symposia on Quantum Chemistry and Biochemistry ((JSQC,volume 12))

Abstract

A particular type of catalysis that has been attracting increasing attention in recent years is that due to a properly situated hydroxyl group which facilitates the opening of an epoxide ring by means of intra-molecular hydrogen bonding. This has been proposed, for several molecules of biochemical interest, as a means of explaining their high degrees of reactivity.

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

Access this chapter

Log in via an institution
Chapter
USD 29.95
Price excludes VAT (USA)
  • Available as PDF
  • Read on any device
  • Instant download
  • Own it forever
eBook
USD 129.00
Price excludes VAT (USA)
  • Available as PDF
  • Read on any device
  • Instant download
  • Own it forever
Softcover Book
USD 169.99
Price excludes VAT (USA)
  • Compact, lightweight edition
  • Dispatched in 3 to 5 business days
  • Free shipping worldwide - see info
Hardcover Book
USD 169.99
Price excludes VAT (USA)
  • Durable hardcover edition
  • Dispatched in 3 to 5 business days
  • Free shipping worldwide - see info

Tax calculation will be finalised at checkout

Purchases are for personal use only

Institutional subscriptions

Preview

Unable to display preview. Download preview PDF.

Unable to display preview. Download preview PDF.

References

  1. R. T. Morrison and R. N. Boyd (1973)Organic Chemistry, 3rd ed., Allyn and Bacon, Inc., Boston, ch. 17.

    Google Scholar 

  2. A. C. Hopkinson, M. H. Lieu, I. G. Csizmadia and K. Yates (1978) Theoret. Chim. Acta47 97.

    Google Scholar 

  3. P. Politzer, K. C. Daiker, V. M. Estes and M. Baughman (1978) Internat. J. Quantum Chem., Quantum Biol. Symp. No. 5, 291.

    CAS  Google Scholar 

  4. J. E. Ferrell, Jr. and G. H. Loew (1979) J. Amer. Chem. Soc.101 1385.

    Article  CAS  Google Scholar 

  5. S. M. Kupchan, W. A. Court, R. G. Dailey, Jr., C. J. Gilmore and R. F. Bryan (1972) J. Amer. Chem. Soc.94 7194.

    Article  CAS  Google Scholar 

  6. S. M. Kupchan and R. M. Schubert (1974) Science185 791.

    Article  CAS  Google Scholar 

  7. D. H. R. Barton and Y. Houminer (1973) J. C. S. Chem. Comm. 839.

    Google Scholar 

  8. Y. Houminer (1975) J. C. S. Perkin Trans. 1, 1663.

    Article  Google Scholar 

  9. I. B. Weinstein, A. M. Jeffrey, K. W. Jennette, S. H. Blobstein, R. G. Harvey, C. Harris, H. Autrup, H. Kasai and K. Nakanishi (1976) Science193 592.

    Google Scholar 

  10. P. G. Wislocki, A. W. Wood, R. L. Chang, W. Levin, H. Yagi, O. Hernandez, D. M. Jerina and A. H. Conney (1976) Biochem. Biophys. Res. Commun.68 1006.

    Google Scholar 

  11. S. K. Yang, P. R. Roller and H. V. Gelboin (1978) in:Carcinogenesis, Vol. 3: Polynuclear Aromatic Hydrocarbons, P. W. Jones and R. I. Frendenthal, eds., Raven Press, New York, p. 285.

    Google Scholar 

  12. M. Koreeda, P. D. Moore, P. G. Wislocki, W. Levin, A. H. Conney, H. Yagi and D. M. Jerina (1978) Science199 778.

    Article  CAS  Google Scholar 

  13. A. M. Jeffrey, K. W. Jennette, S. H. Blobstein, I. B. Weinstein, F. A. Beland, R. G. Harvey, H. Kasai, I. Miura and K. Nakanishi (1976) J. Amer. Chem. Soc.98 5714.

    Article  CAS  Google Scholar 

  14. K. Nakanishi, H. Kasai, H. Cho, R. G. Harvey, A. M. Jeffrey, K. W. Jennette and I. B. Weinstein (1977) J. Amer. Chem. Soc.99 258.

    Article  CAS  Google Scholar 

  15. H. Yagi, D. R. Thakker, O. Hernandez, M. Koreeda and D. M. Jerina (1977) J. Amer. Chem. Soc.99 1604.

    Article  CAS  Google Scholar 

  16. D. M. Jerina, H. Yagi, O. Hernandez, P. M. Dansette, A. W. Wood, W. Levin, R. L. Chang, P. G. Wislocki and A. H. Conney (1976) in:Carcinogenesis, Vol. 1, Polynuclear Aromatic Hydrocarbons: Chemistry, Metabolism and Carcinogenesis, R. I. Freudenthal and P. W. Jones, eds., Raven Press, New York, p. 91.

    Google Scholar 

  17. D. L. Whalen, A. M. Ross, H. Yagi, J. M. Karle and D. M. Jerina (1978) J. Amer. Chem. Soc.100 5218.

    Article  CAS  Google Scholar 

  18. H. Yagi, O. Hernandez and D. M. Jerina (1975) J. Amer. Chem. Soc.97 6881.

    Article  CAS  Google Scholar 

  19. P. B. Hulbert (1975) Nature 256 146.

    Article  CAS  Google Scholar 

  20. J. W. Keller, C. Heidelberger, F. A. Beland and R. G. Harvey (1976) J. Amer. Chem. Soc.98 8276.

    Article  CAS  Google Scholar 

  21. H. C. Dalzell, R. K. Razdan and R. Sawdaye (1976) J. Org. Chem.41 1650.

    Article  CAS  Google Scholar 

  22. P. Politzer, K. C. Daiker and V. M. Estes (1979) Internat. J. Quantum Chem., Quantum Biol. Symp. No. 6, in press.

    Google Scholar 

  23. Program developed by W. J, Hehre, W. A. Lathan, R. Ditchfield, M. E. Newton and J. A. Pople; available from Quantum Chemistry Program Exchange, Indiana University, Bloomington, IN, 47401, program #236.

    Google Scholar 

  24. R. Lavery and B. Pullman (1979) Internat. J. Quantum Chem.,in press.

    Google Scholar 

  25. C. Y. Yeh, P. P. Fu, F. A. Beland and R. G. Harvey (1978) Bioorg. Chem.7 497.

    Article  CAS  Google Scholar 

  26. G. J. Kasperek, T. C. Bruice, H. Yagi and R. M. Jerina (1972) J. C. S. Chem. Comm. 784.

    Google Scholar 

  27. G. J. Kasperek and T. C. Bruice (1972) J. Amer. Chem. Soc.94 198.

    Article  CAS  Google Scholar 

  28. G. J. Kasperek, T. C. Bruice, H. Yagi, N. Kanbisch and D. M. Jerina (1972) J. Amer. Chem. Soc.94 7876.

    Article  Google Scholar 

  29. D. L. Whalen, J. A. Montemarano, D. R. Thakker, H. Yagi and D. M. Jerina (1977) J. Amer. Chem. Soc.99 5522.

    Article  CAS  Google Scholar 

  30. R. S. Mulliken (1955) J. Chem. Phys.23 1833.

    Article  CAS  Google Scholar 

  31. J. J. Kaufman, H. E. Popkie, S. Palalikit and P. C. Hariharan (1978) Internat. J. Quantum Chem.14 793; J. J. Kaufman, private communication.

    Google Scholar 

  32. Tables of Interatomic Distances and Configuration in Molecules and Ions (1958, 1965) L. E. Sutton, ed., The Chemical Society, London, Spec. Pub. Nos. 11 and 18.

    Google Scholar 

  33. P. Politzer and K. C. Daiker in:The Force Concept in Chemistry, B. M. Deb, ed., Van Nostrand Reinhold, New York, ch. 7.

    Google Scholar 

  34. L. Pauling (1960)The Nature of the Chemical Bond, 3rd ed., Cornell University Press, Ithaca, N.Y., ch. 12.

    Google Scholar 

Download references

Author information

Authors and Affiliations

  1. Chemistry Department, University of New Orleans, New Orleans, LA, 70122, USA

    Peter Politzer & Vernon M. Estes

Authors
  1. Peter Politzer
    View author publications

    You can also search for this author in PubMed Google Scholar

  2. Vernon M. Estes
    View author publications

    You can also search for this author in PubMed Google Scholar

Editor information

Editors and Affiliations

  1. Institut de Biologie Physico-Chimique (Fondation Edmond de Rothschild), Université Pierre et Marie Curie (PARIS VI), Paris, France

    Bernard Pullman

Rights and permissions

Reprints and permissions

Copyright information

© 1979 D. Reidel Publishing Company

About this paper

Cite this paper

Politzer, P., Estes, V.M. (1979). The Catalytic Effect of Hydrogen Bonding Upon Epoxide Ring-Opening. In: Pullman, B. (eds) Catalysis in Chemistry and Biochemistry Theory and Experiment. The Jerusalem Symposia on Quantum Chemistry and Biochemistry, vol 12. Springer, Dordrecht. https://doi.org/10.1007/978-94-009-9513-0_25

Download citation

  • DOI: https://doi.org/10.1007/978-94-009-9513-0_25

  • Publisher Name: Springer, Dordrecht

  • Print ISBN: 978-94-009-9515-4

  • Online ISBN: 978-94-009-9513-0

  • eBook Packages: Springer Book Archive

Publish with us

Policies and ethics

Search

Navigation