Enantiomeric Recognition of Organic Ammonium Salts by Chiral Dialkyl-, Dialkenyl-, and Tetramethyl-Substituted Pyridino-18-crown-6 and Tetramethyl-Substituted Bis-pyridino-18-crown-6 Ligands: Comparison of Temperature-Dependent lH NMR and Empirical Force Field Techniques1

Journal of Organic Chemistry

Volumn 55, Issue 10, 1990, Pages 3129-3137

  Bradshaw, Jerald S ^a   Huszthy, Peter ^a   McDaniel, Christopher W ^a   Zhu, Cheng Y ^a   Dailey, N Kent ^a   Izatt, Reed M ^a   Lifson, Shneior ^b  

^a BRIGHAM YOUNG UNIVERSITY   (United States)

^b WEIZMANN INSTITUTE OF SCIENCE   (Israel)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0001501798     PISSN: 00223263     EISSN: 15206904     Source Type: Journal    
DOI: 10.1021/jo00297a031     Document Type: Article

References (37)

1. Presented at the 197th National Meeting of the American Chemical Society. Dallas. Texas. April 9–14. 1989.
2. Gokel, G. W.; Timko, J. M.; Cram, D. J. J. Chem. Soc., Chem. Commun. 1975. 394.
3. Lingenfelter, D. S.; Helgeson, R. C.; Cram, D. J. J. Org. Chem. 1981. 46. 393.
4. Artz, S. P.; deGrandpre, M. P.; Cram, D. J. J. Org. Chem. 1985, 50, 1456.
5. Newcomb, M.; Toner, J. L.; Helgeson, R. C.; Cram, D. J. J. Am. Chem.Soc. 1979, 101, 4941.
6. Sogah, G. D. Y.; Cram, D. J. J. Am. Chem. Soc. 1979, 101, 3035.
7. Lehn, J.-M.: Sirlin, C. J. Chem. Soc. Chem. Commun. 1978. 949.
8. Lehn, J.-M. Science 1985. 227. 849.
9. Potvin, P. G.; Lehn, J.-M. “Design of Cation and Anion Receptors, Catalysts and Carriers” in Synthesis of Macrocycles: The Design of Selective Complexing Agents; Izatt, R. M., Christensen, J. J., Eds.; Wiley-Interscience: New York, 1987; pp 167–239.
10. Curtis, W. D.; Laidler, D. A.; Stoddart, J. F.; Jones, G. H. J. Chem. Soc., Perkin Trans. 1 1977, 1756.
11. Stoddart, J. F. “Synthetic Chiral Receptor Molecules from National Products” in Progress in Macrocyclic Chemistry, Vol. 2; Izatt, R. M., Christensen, J. J., Eds.; Wiley-Interscience: New York, 1981; pp 173–250.
12. Chadwick, D. J.; Cliffe, I. A.; Sutherland, I. O. J. Chem. Soc., Chem. Commun. 1981. 992.
13. Davidson, R. B.; Bradshaw, J. S.; Jones, B. A.; Dailey, N. K.; Christensen, J. J.; Izatt, R. M.; Morin, F. G.; Grant, D. M. J. Org. Chem. 1984, 49. 353.
14. Bradshaw, J. S.; Thompson, P. K.; Izatt, R. M.; Morin, F. G.; Grant, D. M. J. Heterocyl. Chem. 1984, 21, 897.
15. Bradshaw, J. S.; Chamberlin, D. A.; Harrison, P. E.; Wilson, B. E.; Arena, G.; Dailey, N. K.; Lamb, J. D.; Izatt, R. M.; Morin, F. G.; Grant, D. M. J. Org. Chem. 1985, 50, 3065.
16. Bradshaw, J. S.; Colter, M. L.; Nakatsuji, Y.; Spencer, N. O.; Brown, M. F.; Izatt, R. M.; Arena, G.; Tse, P.-K.; Wilson, B. E.; Lamb, J. D.; Dailey, N. K.; Morin, F. G.; Grant, D. M. J. Org. Chem. 1985, 50, 4865.
17. Bradshaw, J. S.; Maas, G. E.; Lamb, J. D.; Izatt, R. M.; Christensen, J. J. J. Am. Chem. Soc. 1980. 102. 467.
18. Stoddart, J. F. “Chiral Crown Ethers” in Topics in Stereochmistry, Vol. 17; Eliel, E. L., Wilen, S. H., Eds.; Wiley-Interscience: New York. 1988: pp 207–288.
19. Lifson, S.; Felder, C. E.; Shanzer, A. J. Am. Chem. Soc. 1983, 105, 3866.
20. Lifson, S.; Felder, C. E.; Shanzer, A.; Libman, J. In Progress in Macrocyclic Chemistry, Vol. 3; Izatt, R. M., Christensen, J. J., Eds.; Wiley-Interscience: New York, 1987; pp 241–308.
21. Lifson, S.; Felder, C. E.; Dobler, M. Acta Crystallogr. 1987, B43, 179.
22. Tor, Y.; Libman, J.; Shanzer, A.; Lifson, S. J. Am. Chem. Soc. 1987. 109. 6517.
23. Bradshaw, J. S.; Izatt, R. M.; Christensen, J. J.; Krakowiak, K. E.; Tarbet, B. J.; Bruening, R. L.; Lifson, S. J. Incl. Phenom. 1989, 7, 127.
24. Koppenhoefer, B.; Schurig, V. Org. Synth. 1987, 66, 151.
25. Koppenhoefer, B.; Schurig, V. Org. Synth. 1987, 66, 160.
26. Cooper, K. D.: Walborsky, H. M. J. Org. Chem. 1981, 46, 2110.
27. Jones, B. A.; Bradshaw, J. S.; Izatt, R. M. J. Heterocyl. Chem. 1982, 19, 551.
28. Bradshaw, J. S.; Jolley, S. T. J. Heterocycl. Chem. 1979,16, 1157.
29. Eibl, H. Chem. Phys. Lipids 1981, 28, 1.
30. Krakowiak, K. Polish J. Chem. 1986. 60. 277.
31. Sutherland, I. O. Annu. Rep. NMR Spectrosc. 1971, 4, 71.
32. Baxter, S. L.; Bradshaw, J. S. J. Heterocycl. Chem. 1981, 18, 233.
33. Hiraro, T.; Inoue, S.; Tsurata, T. Makromol. Chem. 1976, 177, 3245.
34. Baer, E.; Fisher, O. L. J. Am. Chem. Soc. 1948, 70, 609.
35. Nelson, W. L.; Wennerstrom, J. E.; Sankar, S. R. J. Org. Chem. 1977, 42, 1006.
36. Sheldrick, G. M. SHELXTL. An Integrated System for Solving Refining and Displaying Crystal Structures from Diffraction Data, 4th revision University of Gottingen, Federal Republic of Germany, 1983.
37. International Tables of X-ray Crystallography, Vol. 4; Ibers, J. A., Hamilton, W. C., Eds.; Kynock Press: Birmingham, England, 1974; p 99.