Skip to main content

Effects of Substituents in Quinonoid Compounds

  • Chapter
Substituent Effects in Organic Polarography

Abstract

It was shown in Chapter II that a measure of the influence of the substituent on the redox potential of a reversible electrode system is provided by the change in the increment of the standard free energy in the interconversion of the oxidized and reduced forms. The shift in the redox potential (or half-wave potential, denoted by Δ1/2), defined as Δ 1/2 = (1/2)x — ( 1/2)H (where the index X denotes the compound containing the substituent X and the index H the parent reference compound) is proportional to the difference of the logarithms of the equilibrium constants KX and KH of the corresponding reversible process

$$\Delta E{{{}^\circ }_{1/2}}\sim \ln \frac{{{K}_{X}}}{{{K}_{H}}}$$
(58)

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

Access this chapter

eBook
USD 16.99
Price excludes VAT (USA)
  • Available as PDF
  • Read on any device
  • Instant download
  • Own it forever
Softcover Book
USD 16.99
Price excludes VAT (USA)
  • Compact, lightweight 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. W. M. Clark, “Oxidation—Reduction Potentials of Organic Systems,” Williams and Wilkins, Baltimore, 1960.

    Google Scholar 

  2. M. Kalousek and M. Rdlek, Collection Czech. Chem. Commun. 19: 1099 (1954); Chem. Listy 48: 808 (1954).

    Google Scholar 

  3. R. W. Taft, Jr., Separation of Polar, Steric, and Resonance Effects in Reactivity in “Steric Effects in Organic Chemistry” (M. S. Newman ed.) John Wiley and Sons, New York, 1956.

    Google Scholar 

  4. L. P. Hammett, “Physical Organic Chemistry,” p. 184, McGraw-Hill, New York, 1940.

    Google Scholar 

  5. H. H. Jaffé, Chem. Rev. 53: 191 (1953).

    Article  Google Scholar 

  6. M. G. Evans and J. De Heer, Quart. Rev. 4: 94 (1950).

    Article  CAS  Google Scholar 

  7. P. Zuman, Collection Czech. Chem. Commun. 27: 2035 (1962).

    Article  Google Scholar 

  8. M. Charton, A paper presented before the Meeting of the American Chemical Society (1961).

    Google Scholar 

  9. T. Hayashi and R. Shibata, Kogyo Kagaku Zasshi 63 : 840 (1960) ;

    Google Scholar 

  10. T. Hayashi and R. Shibata, quoted according to T. Hayashi and R. Shibata, Bull. Chem. Soc. Japan 34: 1116 (1961).

    Article  CAS  Google Scholar 

  11. O. Ryba, J. Petrdnek, and J. Pospísil, Collection Czech. Chem. Commun. 30: 843 (1965).

    Article  CAS  Google Scholar 

  12. O. Ryba, J. Petrânek, and J. Pospísil, Collection Czech. Chem. Commun. 30: 2157 (1965).

    Article  CAS  Google Scholar 

  13. D. E. Kvalnes, J. Am. Chem. Soc. 56: 667, 2478 (1934).

    Google Scholar 

  14. E. Bilman, A. L. Jensen, and K. O. Pederson, J. Chem. Soc. 127: 199 (1925).

    Article  Google Scholar 

  15. J. B. Conant and L. F. Fieser, J. Am. Chem. Soc. 45: 2194 (1923).

    Article  CAS  Google Scholar 

  16. J. B. Conant and L. F. Fieser, J. Am. Chem. Soc. 46: 1858 (1924).

    Article  CAS  Google Scholar 

  17. V. K. LaMer and L. E. Baker, J. Am. Chem. Soc. 44: 1954 (1922).

    Article  CAS  Google Scholar 

  18. J. B. Conant and L. F. Fieser, J. Am. Chem. Soc. 44: 2480 (1922).

    Article  CAS  Google Scholar 

  19. R. T. Arnold and H. E. Zaugg, J. Am. Chem. Soc. 63: 1317 (1941).

    Article  CAS  Google Scholar 

  20. E. Scrocco and G. Marmani, Ann. Chim. (Rome) 41: 716 (1951).

    CAS  Google Scholar 

  21. L. I. Smith, I. M. Kolthoff, S. Wawzonek, and P. M. Ruoff, J. Am. Chem. Soc. 63; 1018 (1941).

    Article  CAS  Google Scholar 

  22. M. E. Peover, J. Chem. Soc. 1962: 4540.

    Google Scholar 

  23. O. Dimroth, Angew. Chem. 46: 571 (1933).

    Article  CAS  Google Scholar 

  24. H. Berg, Z. Chem. 2: 237 (1962).

    Article  Google Scholar 

  25. R. L. Bent, J. C. Dessloch, F. C. Duennebier, D. W. Fassett, D. B. Glass, T. H. James, D. B. Julian, W. R. Ruby, J. M. Snell, J. H. Sterrer, J. R. Thirtle, P. W. Vittum, and A. Weissberger, J. Am. Chem. Soc. 73: 3100 (1951).

    Article  CAS  Google Scholar 

  26. L. F. Fieser and M. Fieser, “Lehrbuch der organischen Chemie,” Verlag Chemie, Weinheim, 1954.

    Google Scholar 

  27. P. Zuman, Chem. Listy 48, 94 (1954).

    CAS  Google Scholar 

  28. F. T. Eggertsen and F. T. Weiss, Anal. Chem. 28: 1008 (1956).

    Article  CAS  Google Scholar 

  29. L. F. Fieser and M. Fieser, J. Am. Chem. Soc. 57; 491 (1935).

    Article  CAS  Google Scholar 

  30. K. Wallenfels and W. Möhle, Ber. 76: 924 (1943).

    Google Scholar 

  31. E. G. Ball, J. Biol. Chem. 114: 649 (1936).

    Google Scholar 

  32. L. F. Fieser, J. Am. Chem. Soc. 50, 439 (1928).

    Article  Google Scholar 

  33. N. Ikeda, J. Pharm. Soc. Japan 75: 1073 (1955).

    CAS  Google Scholar 

  34. I. F. Vladimircev and A. G. Stromberg, Zh. Obshch. Khim. 27: 1029 (1957).

    Google Scholar 

  35. P. Zuman, unpublished results.

    Google Scholar 

  36. L. F. Lugg, A. K. Macbeth, and F. L. Winsor, J. Chem. Soc. 1936: 145, 1457.

    Article  Google Scholar 

  37. P. Zuman, Collection Czech. Chem. Commun. 19: 1140 (1954); Chem. Listy 48: 524 (1954).

    Google Scholar 

  38. V. E. Dicent, Zh. Obshch. Khim. 29: 1370 (1959).

    Google Scholar 

  39. L. Stârka, L. Vystrcil, and B. Stârkovâ, Chem. Listy 51: 1440 (1957).

    Google Scholar 

  40. 39 L. A. Wiles, J. Chem. Soc. 1952: 1958.

    Google Scholar 

  41. R. J. Crawford, S. Levine, R. M. Elofson, and R. B. Sandin, J. Am. Chem. Soc. 79: 3153 (1957).

    Article  CAS  Google Scholar 

  42. R. Jones and T. McL. Spotswood, Australian J. Chem. 15: 492 (1962).

    Article  CAS  Google Scholar 

  43. M. E. Peover, Nature 193, 475 (1962).

    Article  CAS  Google Scholar 

  44. M. E. Peover, Nature 191, 702 (1961).

    Article  CAS  Google Scholar 

  45. M. E. Peover, Trans. Faraday Soc. 58: 1656 (1962).

    CAS  Google Scholar 

  46. M. E. Peover and J. D. Davies, Trans. Faraday Soc. 60: 476 (1964).

    Article  CAS  Google Scholar 

  47. E. Braude, L. Jackmann, and R. Linstead, J. Chem. Soc. 1954: 3548.

    Google Scholar 

  48. H. Musso, K. Figge, and D. J. Becker, Chem. Ber. 94: 1107 (1961).

    Article  Google Scholar 

Download references

Author information

Authors and Affiliations

Authors

Rights and permissions

Reprints and permissions

Copyright information

© 1967 Plenum Press

About this chapter

Cite this chapter

Zuman, P. (1967). Effects of Substituents in Quinonoid Compounds. In: Substituent Effects in Organic Polarography. Springer, New York, NY. https://doi.org/10.1007/978-1-4684-8661-2_8

Download citation

  • DOI: https://doi.org/10.1007/978-1-4684-8661-2_8

  • Publisher Name: Springer, New York, NY

  • Print ISBN: 978-1-4684-8663-6

  • Online ISBN: 978-1-4684-8661-2

  • eBook Packages: Springer Book Archive

Publish with us

Policies and ethics