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Stable silica gel-bound crown ethers. Selective separation of metal ions and a potential for separations of amine enantiomers

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Abstract

Silica gel-bound crown ethers and aza macrocycles have been synthesized with the attaching arm connected to the carbon framework of the macrocycles. The interactions of these bound macrocycles with cations are almost identical to those involving the analogous free macrocycles. This has allowed for predictable cation separation, concentration, and removal processes to be performed on a small scale. Quantum mechanical calculations and NMR measurements indicate that similarly bound chiral macrocycles will be capable of use in separating chiral organic amines.

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References

  1. C. J. Pedersen:J. Am. Chem. Soc. 89, 7077 (1967).

    Google Scholar 

  2. D. J. Cram:Science 219, 1177 (1983).

    Google Scholar 

  3. J. M. Lehn:Science 227, 849 (1985).

    Google Scholar 

  4. C & E N, October 19, 1987, pp.4, 5.

  5. R. M. Izatt, J. S. Bradshaw, S. A. Nielsen, J. D. Lamb, J. J. Christensen and D. Sen:Chem. Rev. 85, 271 (1985).

    Google Scholar 

  6. R. M. Izatt, G. C. LindH, R. L. Bruening, J. S. Bradshaw, J. D. Lamb and J. J. Christensen:Pure Appl. Chem. 58, 1453 (1986).

    Google Scholar 

  7. J. S. Bradshaw, R. L. Bruening, K. E. Krakowiak, B. J. Tarbet, M. L. Bruening, R. M. Izatt and J. J. Christensen: J. Chem. Soc., Chem. Commun. 812 (1988).

  8. J. J. Christensen, S. P. Christensen, M. P. Biehl, S. A. Lowe, J. D. Lamb and R. M. Izatt:Sep. Sci. Technol. 18, 363 (1983).

    Google Scholar 

  9. R. M. Izatt, G. C. LindH, R. L. Bruening, P. Huszthy, C. W. McDaniel, J. S. Bradshaw and J. J. Christensen:Anal. Chem. 60, 1694 (1988).

    Google Scholar 

  10. R. M. Izatt, G. C. LindH, G. A. Clark, Y. Nakatsuji, J. S. Bradshaw, J. D. Lamb and J. J. Christensen:J. Membrane Sci. 31, 1 (1985).

    Google Scholar 

  11. R. M. Izatt, G. C. LindH, R. L. Bruening, P. Huszthy, J. D. Lamb, J. S. Bradshaw and J. J. Christensen:J. Incl. Phenom. 5, 739 (1987).

    Google Scholar 

  12. J. D. Lamb, R. L. Bruening, R. M. Izatt, Y. Hirashima, P. K. Tse, and J. J. Christensen:J. Membrane Sci. 37, 13 (1988).

    Google Scholar 

  13. R. M. Izatt, R. L. Bruening, M. L. Bruening, G. C. LindH, and J. J. Christensen:Anal. Chem., in press.

  14. R. M. Izatt, R. L. Bruening, M. L. Bruening, B. J. Tarbet, K. E. Krakowiak, J. S. Bradshaw and J. J. Christensen:Anal. Chem.,60, 1825 (1988).

    Google Scholar 

  15. J. S. Bradshaw, K. E. Krakowiak, R. L. Bruening, B. J. Tarbet, P. B. Savage and R. M. Izatt:J. Org. Chem. 53, 3190 (1988).

    Google Scholar 

  16. I. Ikeda, S. Yamamura, Y. Nakatsuji and M. Okahara:J. Org. Chem. 45, 5355 (1980).

    Google Scholar 

  17. H. Stetter and J. Marx:Liebigs Ann. Chem. 607, 59 (1957).

    Google Scholar 

  18. J. M. Lehn:Acts. Chem. Res. 11, 49 (1978).

    Google Scholar 

  19. D. A. Babb, B. P. Czech and R. A. Bartsch:J. Heterocyclic Chem. 23, 609 (1986).

    Google Scholar 

  20. K. E. Krakowiak and J. S. Bradshaw:J. Org. Chem.,53, 1808 (1988).

    Google Scholar 

  21. K. Kuo, M. Miki, 1. Ikeda and M. Okahara:Tetrahedron Lett., 4273 (l978).

  22. H. Frensdorf:J. Am. Chem. Soc. 93, 600 (l971).

    Google Scholar 

  23. R. M. Izatt, R. E. Terry, D. P. Nelson, Y. Chan, D. J. Eatough, J. S. Bradshaw, L. D. Hansen and J. J. Christensen:J. Am. Chem. Soc. 98, 7626 (1976).

    Google Scholar 

  24. See M. Takagi and H. Nakamura:J. Coord. Chem. 15, 53 (1986) for a review.

    Google Scholar 

  25. R. S. Paredes, N. S. Valera and L. F. Lindoy:Aust. J. Chem. 39, 1071 (1986).

    Google Scholar 

  26. J. S. Bradshaw, B. A. Jones, R. B. Davidson, J. J. Christensen, J. D. Lamb, R. M. Izatt, F. G. Morin and D. M. Grant:J. Org. Chem. 47, 3362 (1982).

    Google Scholar 

  27. B. A. Jones, J. S. Bradshaw, P. R. Brown, J. J. Christensen and R. M. Izatt:J. Org. Chem. 48, 2635 (1983).

    Google Scholar 

  28. R. B. Davidson, J. S. Bradshaw, B. A. Jones, N. K. Dalley, J. J. Christensen, R. M. Izatt, F. G. Morin and D. M. Grant: J. Org. Chem. 49, 353 (1984).

    Google Scholar 

  29. J. S. Bradshaw, P. K. Thompson, R. M. Izatt, F. G. Morin and D. M. Grant:J. Heterocyclic Chem. 21, 897 (1984).

    Google Scholar 

  30. S. Lifson, C. E. Felder and A. Shanzer:J. Am. Chem. Soc. 105, 3866 (1983).

    Google Scholar 

  31. S. Lifson, C. E. Felder, A. Shanzer and J. Libman: inProgress in Macrocyclic Chemistry, Vol. 3 (Eds. R. M. Izatt and J. J. Christensen), pp. 241–308, Wiley Interscience (l987).

  32. S. Lifson, C. E. Felder and M. Dobler:Acta Crystallogr. B 43, 179 (l987).

    Google Scholar 

  33. Y. Tor, J. Libman, A. Shanzer and S. Lifson:J. Am. Chem. Soc. 109, 6517 (1987).

    Google Scholar 

  34. G. D. Y. Sogah and D. J. Cram:J. Am. Chem. Soc. 101, 3035 (1979).

    Google Scholar 

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Authors and Affiliations

  1. Departments of Chemistry and Chemical Engineering, Brigham Young University, UT 84602, Provo, USA

    Jerald S. Bradshaw, Reed M. Izatt, James J. Christensen, Bryon J. Tarbet & Ronald L. Bruening

  2. Department of Chemical Physics, Weizmann Institute of Science, 76100, Rehovot, Israel

    S. Lifson

  3. Department of Chemical Technology, School of Medicine, 90145, Lodz, Poland

    Krzystof E. Krakowiak

Authors
  1. Jerald S. Bradshaw
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  2. Reed M. Izatt
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  3. James J. Christensen
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  4. Krzystof E. Krakowiak
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  5. Bryon J. Tarbet
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  6. Ronald L. Bruening
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  7. S. Lifson
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Dedicated to the memory of Professor James J. Christensen who died on 5 September 1987.

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Bradshaw, J.S., Izatt, R.M., Christensen, J.J. et al. Stable silica gel-bound crown ethers. Selective separation of metal ions and a potential for separations of amine enantiomers. J Incl Phenom Macrocycl Chem 7, 127–136 (1989). https://doi.org/10.1007/BF01060715

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  • DOI: https://doi.org/10.1007/BF01060715

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