Calixarenes. 15. The Formation of Complexes of Calixarenes with Neutral Organic Molecules in Solution

Journal of the American Chemical Society

Volumn 107, Issue 21, 1985, Pages 6063-6069

  Bauer, Lorenz J ^a   Gutsche, C David ^a  

^a WASHINGTON UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 33845379564     PISSN: 00027863     EISSN: 15205126     Source Type: Journal    
DOI: 10.1021/ja00307a040     Document Type: Article

References (36)

1. Gutsche, C. D. Acc. Chem. Res. 1983, 16, 161. Gutsche, C. D. “Topics in Current Chemistry”; Boschke, F. L., Ed.; Springer-Verlag: New York, 1984, Vol 123, p 1.
2. Gutsche, C. D.; Dhawan, B.; No, K. H.; Muthukrishnan, R. J. Am. Chem. Soc. 1981, 103, 3782.
3. Coruzzi, M.; Andreetti, G. D.; Bocchi, V.; Pochini, A.; Ungaro, R. J. Chem. Soc., Perkin Trans. 2 1982, 1133.
4. Andreetti, G. D.; Ungaro, R.; Pochini, A. J. Chem. Soc., Chem. Commun. 1979, 1005.
5. Ninagawa, A.; Matsuda, H. Makromol. Chem. Rapid Commun. 1982, 3, 65.
6. Nakamoto, Y.; Ishida, S. Makromol. Chem. Rapid Commun. 1982, 3, 705.
7. Cram (Cram, D. J.; Cram, J. M. Science 1974, 183, 803) refers to complex formation as “host-guest” interaction. Lehn (Lehn, J.-M. Pure. Appl. Chem. 1978, 50, 871; 1979, 51, 979) refers to it as “receptor-substrate” interaction.
8. (a) Bender, M. L.; Komiyama, M. “Cyclodextrin Chemistry”; Springer-Verlag: Berlin, 1978. (b) Saenger, W. Angew. Chem., Int. Ed. Engl. 1980, 19, 344. (c) Breslow, R. Acc. Chem. Res. 1980, 13, 170. (d) Tabushi, I. Acc. Chem. Res. 1982 15, 66.
9. (a) Vogtle, F., Ed. “Host Guest Chemistry”; Springer-Verlag: Berlin, 1981; Vol. 1. (b) Izatt, R. M., Christensen, J. J., Eds. “Synthetic Multidentate Macrocyclic Compounds”; Academic Press: New York, 1978 and 1979; Vol. I and II.
10. Lehn, J.-M. Acc. Chem. Res. 1978, 11, 49.
11. (a) Keehn, P. M., Rosenfeld, S. M., Eds.; “Cyclophanes”; Academic Press: New York, 1983; Vol. 1 and II. (b) Tabushi, I.; Yamamura, K. In “Cyclophanes I”; Springer-Verlag: Berlin, 1983; Vol. 113. (c) Tabushi, I.; Kuroda, Y. Adv. Catal. 1983, 32, 417.
12. (a) Komiyama, M.; Bender, M. L. J. Am. Chem. Soc. 1978, 100, 2259. (b) Tabushi, I.; Kiyosuke, Y.; Sugimoto, T.; Yamamura, K. J. Am. Chem. Soc. 1978, 100, 916. (c) Bergeron, R. J.; Channing, M. A.; Gibeily, G. I.; Pillor, D. M. J. Am. Chem. Soc. 1977, 99, 5146.
13. Wojcik, J. F. Bioorg. Chem. 1984, 12, 130.
14. (a) Odashima, K.; Itai, A.; Iitaka, Y.; Arata, Y.; Koga, K. Tetrahedron Lett. 1980, 21, 4347. (b) Odashima, K.; Itai, A.; Iitaka, Y.; Koga, K. J. Am. Chem. Soc. 1980, 102, 2504. (c) Tabushi, I.; Kuroda, Y.; Kimura, Y. Tetrahedron Lett. 1976, 37, 3327. (d) Tabushi, I.; Sasaki, H.; Kuroda, Y. J. Am. Chem. Soc. 1976, 98, 5727. (e) Murakami, Y.; Aoyama, Y.; Kida, M.; Nakano, A. Bull. Chem. Soc. Jpn. 1977, 50, 3365.
15. For example, see the complexation data in: (a) Kondo, H.; Nakatani, H.; Hiromi, K. J. Biochem. (Tokyo) 1976, 79, 393. (b) Tabushi, I.; Shimizu, N.; Sugimoto, T.; Shiozuka, M.; Yamamura, K. J. Am. Chem. Soc. 1977, 99, 7100.
16. (a) Odashima, K.; Soga, T.; Koga, K. Tetrahedron Lett. 1981, 5311. (b) Odashima, K.; Koga, K. Heterocycles 1981, 15, 1151. (c) Soga, T.; Odashima, K.; Koga, K. Tetrahedron Lett. 1980, 4351.
17. Cram, D. J. Science Washington D.C. 1983, 219, 1177. Helgeson, R. C.; Mazaleyrat, J.-P.; Cram, D. J. J. Am. Chem. Soc. 1981, 103, 3929.
18. (a) McKervey, M. A.; Mulholland, D. L. J. Chem. Soc., Chem. Commun. 1977, 438. (b) van der Leij, M.; Oosterink, H. J.; Hall, R. H.; Reinhoudt, D. N. Tetrahedron 1981, 37, 3661.
19. Cram, D. J.; Kaneda, T.; Helgeson, R. C.; Lein, G. M. J. Am. Chem. Soc. 1979, 101, 6752. Cram, D. J.; Dicker, I. B.; Knobler, C. B.; Trueblood, K. N. J. Am. Chem. Soc. 1982, 104, 6828.
20. Jarvi, E. T.; Whitlock, H. W. J. Am. Chem. Soc. 1982, 104, 7196.
21. deBoer, J. A. A.; Reinhoudt, D. N.; Harkema, S.; van Hummel, G. J.; deJong, F. J. Am. Chem. Soc. 1982, 104, 4073.
22. Williams, D. H. Tetrahedron Lett. 1965, 2305. For a concise exposition of this technique as applied to the study of complex formation see ref 21.
23. Dhawan, B.; Gutsche, C. D. J. Org. Chem. 1983, 48, 1536.
24. Gutsche, C. D.; Gutsche, A. E.; Karaulov, A. I. J. Inclusion Phenom., in press.
25. Fetizon, M.; Gore, J.; Laszlo, P.; Waegell, B. J. Org. Chem. 1966, 31, 4047.
26. (a) Hanna, M. W.; Ashbaugh, A. L. J. Phys. Chem. 1964, 68, 811. (b) Foster, R.; Fyfe, C. A. Trans. Faraday Soc. 1965, 61, 1626.
27. Bocchi, V.; Foina, D.; Pochini, A.; Ungaro, R.; Andreetti, G. D. Tetrahedron 1982, 38, 373.
28. Gutsche, C. D.; Dhawan, B.; Levine, J. A.; No, K. H.; Bauer, L. J. Tetrahedron 1983, 39, 409.
29. Gutsche, C. D.; Bauer, L. J. J. Am. Chem. Soc., in press. Bauer, L. J.; Gutsche, C. D. J. Am. Chem. Soc., in press.
30. Andreetti, G. D.; Pochini, A.; Ungaro, R. J. Chem. Soc., Perkin Trans. 2 1983, 1773.
31. Gutsche, C. D.; Levine, J. A. J. Am. Chem. Soc. 1982, 104, 2652.
32. (a) Dupont, J.-P.; Neerinck, D.; Lamberts, L. Ann. Chim. (Paris) 1973, 8, 21. (b) Martin, M. J. Chim. Phys. (Paris) 1962, 59, 736. (c) Gordshtein, I. P.; Perepelkova, T. I.; Gur'yanova, E. N.; Kocheskov, K. A. Dokl. Acad. Nauk SSSR 1972, 207, 636. (d) Perepelkova, T. I.; Scherbakova, E. S.; Gordshtein, I. P.; Gur'yanova, E. N., J. Gen. Chem USSR 1975, 45, 641.
33. Barry, J. E.; Finkelstein, M.; Ross, S. D. J. Org. Chem. 1984, 49, 1669.
34. Böhmer, V.; Schade, E.; Vogt, W. Makromol. Chem. Rapid Commun. 1984, 5, 221.
35. Böhmer, V.; Schade, E.; Antes, C.; Pachta, J.; Vogt, W.; Kammerer, H. Makromol. Chem. 1983, 184, 2361.
36. Vold, R. L.; Waugh, J. S.; Klein, M. P.; Phelps, D. E. J. Chem. Phys. 1968, 48, 3831.