Induced circular dichroism of cyclodextrin inclusion complexes: Examining the cavity with a bilateral probe

Organic Letters

Volumn 2, Issue 14, 2000, Pages 1999-2002

  Bobek, Michael M ^a   Krois, Daniel ^a   Brinker, Udo H ^a  

^a INSTITUT FÜR ORGANISCHE CHEMIE   (Austria)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0000641533     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol005923d     Document Type: Article

References (29)

1. Schneider, H.-J.; Hacket, F.; Rüdiger, V.; Ikeda, H. Chem. Rev. 1998, 98, 1755. Connors, K. A. Chem. Rev. 1997, 97, 1325.
2. Schneider, H.-J.; Hacket, F.; Rüdiger, V.; Ikeda, H. Chem. Rev. 1998, 98, 1755. Connors, K. A. Chem. Rev. 1997, 97, 1325.
3. Krois, D.; Brinker, U. H. J. Am. Chem. Soc. 1998, 120, 11627.
4. Brinker, U. H.; Buchkremer, R.; Kolodziejczyk, M.; Kupfer, R.; Rosenberg, M.; Poliks, M. D.; Orlando, M.; Gross, M. L. Angew. Chem., Int. Ed. Engl. 1993, 32, 1344. Brinker, U. H.; Rosenberg, M. G. In Advances in Carbene Chemistry, Vol. II; Brinker, U. H., Ed.; JAI: Stamford, 1998; p 29.
5. Brinker, U. H.; Buchkremer, R.; Kolodziejczyk, M.; Kupfer, R.; Rosenberg, M.; Poliks, M. D.; Orlando, M.; Gross, M. L. Angew. Chem., Int. Ed. Engl. 1993, 32, 1344. Brinker, U. H.; Rosenberg, M. G. In Advances in Carbene Chemistry, Vol. II; Brinker, U. H., Ed.; JAI: Stamford, 1998; p 29.
6. Krois, D.; Bobek, M. M.; Werner, A.; Kählig, H.; Brinker, U. H. Org. Lett. 2000, 2, 315.
7. Isaev S. D.; Kolyada, G. G.; Novikov; S. S.; Yurchenko, A. G. Izv. Akad. Nauk. SSSR, Ser. Khim. 1974, 955. Isaev, S. D.; Karpenko, N. F.; Kolyada, G. G.; Novikov, S. S.; Yurchenko, A. G. J. Org. Chem. USSR 1978, 14, 708.
8. Isaev S. D.; Kolyada, G. G.; Novikov; S. S.; Yurchenko, A. G. Izv. Akad. Nauk. SSSR, Ser. Khim. 1974, 955. Isaev, S. D.; Karpenko, N. F.; Kolyada, G. G.; Novikov, S. S.; Yurchenko, A. G. J. Org. Chem. USSR 1978, 14, 708.
9. Yoshida, N.; Yamaguchi, H.; Iwao, T.; Higashi, M. J. Chem. Soc., Perkin Trans. 2, 1999, 379. Liu, Y.; Li, B.; Han, B.-H.; Wada, T.; Inoue, Y. J. Chem. Soc., Perkin Trans. 2 1999, 563. Mayer, B.; Marconi, G.; Klein, C.; Köhler, G.; Wolschann, P. J. Incl. Phenom. Mol. Recognit. Chem. 1997, 29, 79. Marconi, G.; Monti, S.; Mayer, B.; Köhler, G. J. Phys. Chem. 1995, 99, 3943. Zhdanov, Y. A.; Alekseev, Y. E.; Kompantseva, E. V.; Vergeichik, E. N. Russ. Chem. Rev. 1992, 61, 563. Kajtar, M.; Horvath-Toro, C.; Kuthi, E.; Szejtli, J. Acta Chim. Acad. Sci. Hung. 1982, 110, 327;
10. Yoshida, N.; Yamaguchi, H.; Iwao, T.; Higashi, M. J. Chem. Soc., Perkin Trans. 2, 1999, 379. Liu, Y.; Li, B.; Han, B.-H.; Wada, T.; Inoue, Y. J. Chem. Soc., Perkin Trans. 2 1999, 563. Mayer, B.; Marconi, G.; Klein, C.; Köhler, G.; Wolschann, P. J. Incl. Phenom. Mol. Recognit. Chem. 1997, 29, 79. Marconi, G.; Monti, S.; Mayer, B.; Köhler, G. J. Phys. Chem. 1995, 99, 3943. Zhdanov, Y. A.; Alekseev, Y. E.; Kompantseva, E. V.; Vergeichik, E. N. Russ. Chem. Rev. 1992, 61, 563. Kajtar, M.; Horvath-Toro, C.; Kuthi, E.; Szejtli, J. Acta Chim. Acad. Sci. Hung. 1982, 110, 327;
11. Yoshida, N.; Yamaguchi, H.; Iwao, T.; Higashi, M. J. Chem. Soc., Perkin Trans. 2, 1999, 379. Liu, Y.; Li, B.; Han, B.-H.; Wada, T.; Inoue, Y. J. Chem. Soc., Perkin Trans. 2 1999, 563. Mayer, B.; Marconi, G.; Klein, C.; Köhler, G.; Wolschann, P. J. Incl. Phenom. Mol. Recognit. Chem. 1997, 29, 79. Marconi, G.; Monti, S.; Mayer, B.; Köhler, G. J. Phys. Chem. 1995, 99, 3943. Zhdanov, Y. A.; Alekseev, Y. E.; Kompantseva, E. V.; Vergeichik, E. N. Russ. Chem. Rev. 1992, 61, 563. Kajtar, M.; Horvath-Toro, C.; Kuthi, E.; Szejtli, J. Acta Chim. Acad. Sci. Hung. 1982, 110, 327;
12. Yoshida, N.; Yamaguchi, H.; Iwao, T.; Higashi, M. J. Chem. Soc., Perkin Trans. 2, 1999, 379. Liu, Y.; Li, B.; Han, B.-H.; Wada, T.; Inoue, Y. J. Chem. Soc., Perkin Trans. 2 1999, 563. Mayer, B.; Marconi, G.; Klein, C.; Köhler, G.; Wolschann, P. J. Incl. Phenom. Mol. Recognit. Chem. 1997, 29, 79. Marconi, G.; Monti, S.; Mayer, B.; Köhler, G. J. Phys. Chem. 1995, 99, 3943. Zhdanov, Y. A.; Alekseev, Y. E.; Kompantseva, E. V.; Vergeichik, E. N. Russ. Chem. Rev. 1992, 61, 563. Kajtar, M.; Horvath-Toro, C.; Kuthi, E.; Szejtli, J. Acta Chim. Acad. Sci. Hung. 1982, 110, 327;
13. Yoshida, N.; Yamaguchi, H.; Iwao, T.; Higashi, M. J. Chem. Soc., Perkin Trans. 2, 1999, 379. Liu, Y.; Li, B.; Han, B.-H.; Wada, T.; Inoue, Y. J. Chem. Soc., Perkin Trans. 2 1999, 563. Mayer, B.; Marconi, G.; Klein, C.; Köhler, G.; Wolschann, P. J. Incl. Phenom. Mol. Recognit. Chem. 1997, 29, 79. Marconi, G.; Monti, S.; Mayer, B.; Köhler, G. J. Phys. Chem. 1995, 99, 3943. Zhdanov, Y. A.; Alekseev, Y. E.; Kompantseva, E. V.; Vergeichik, E. N. Russ. Chem. Rev. 1992, 61, 563. Kajtar, M.; Horvath-Toro, C.; Kuthi, E.; Szejtli, J. Acta Chim. Acad. Sci. Hung. 1982, 110, 327;
14. Yoshida, N.; Yamaguchi, H.; Iwao, T.; Higashi, M. J. Chem. Soc., Perkin Trans. 2, 1999, 379. Liu, Y.; Li, B.; Han, B.-H.; Wada, T.; Inoue, Y. J. Chem. Soc., Perkin Trans. 2 1999, 563. Mayer, B.; Marconi, G.; Klein, C.; Köhler, G.; Wolschann, P. J. Incl. Phenom. Mol. Recognit. Chem. 1997, 29, 79. Marconi, G.; Monti, S.; Mayer, B.; Köhler, G. J. Phys. Chem. 1995, 99, 3943. Zhdanov, Y. A.; Alekseev, Y. E.; Kompantseva, E. V.; Vergeichik, E. N. Russ. Chem. Rev. 1992, 61, 563. Kajtar, M.; Horvath-Toro, C.; Kuthi, E.; Szejtli, J. Acta Chim. Acad. Sci. Hung. 1982, 110, 327;
15. Harata, K.; Uedaira, H. Bull. Chem. Soc. Jpn. 1975, 48, 375.
16. Kodaka, M. J. Phys. Chem. 1991, 95, 2110. Kodaka, M. J. Am. Chem. Soc. 1993, 115, 3702. Kodaka, M. J. Phys. Chem. A 1998, 102, 8101.
17. Kodaka, M. J. Phys. Chem. 1991, 95, 2110. Kodaka, M. J. Am. Chem. Soc. 1993, 115, 3702. Kodaka, M. J. Phys. Chem. A 1998, 102, 8101.
18. Kodaka, M. J. Phys. Chem. 1991, 95, 2110. Kodaka, M. J. Am. Chem. Soc. 1993, 115, 3702. Kodaka, M. J. Phys. Chem. A 1998, 102, 8101.
19. Tinoco, I., Jr. Adv. Chem. Phys. 1962, 4, 113.
20. The first attempts to correlate the orientation of a guest molecule inside 7-Cy with its ICD were performed with naphthalene and led to the formulation of Harata's rule (ref 7).
21. Zhang, X.; Nau, W. M. Angew. Chem., Int. Ed. 2000, 39, 544.
22. Bobek, M. M.; Krois, D.; Brehmer, T.; Giester, G.; Schoeller, W. W.; Brinker, U. H. To be published.
23. Butterbaugh, J. S.; Toscano, J. P.; Weaver, W. L.; Gord, J. R.; Hadad, C. M.; Gustavson, T. L.; Platz, M. S. J. Am. Chem. Soc. 1997, 119, 3580.
24. 1@7-Cy is only sparingly soluble in pure water. The addition of ethanol increases the concentration range for the measurements.
25. Cantor, C. R.; Schimmel, P. R. Behavior of Biological Macromoleculs, Part III; Freeman: San Francisco, 1980; p 849. For experimental details see ref 2.
26. Rekharsky, M. V.; Inoue, Y. Chem. Rev. 1998, 98, 1875.
27. This is the case for the spectra of 2-aziadamantane@7-Cy (positive ICD spectrum of Figure 5) and of 2-azi-5-phenyladamantane@7-Cy (negative ICD spectrum of Figure 5). Since the maxima of the UV - vis spectra of 2-aziadamantane and 1 in organic solvents differ by approximately 4 nm, the ICD spectrum of 2-aziadamantane@7-Cy depicted was corrected to a shorter wavelength by 4 nm.
28. Schellman, J. A. Acc. Chem. Res. 1968, 1, 144.
29. Shustov, G. V.; Varlamov, S. V.; Rauk, A.; Kostyanovsky, R. G. J. Am. Chem. Soc. 1990, 112, 3403.