The mechanism of the slippage approach to rotaxanes. Origin of the 'all- or-nothing' substituent effect

Journal of the American Chemical Society

Volumn 120, Issue 36, 1998, Pages 9318-9322

  Raymo, Françisco M ^a   Houk, K N ^a   Stoddart, J Fraser ^a  

^a UNIVERSITY OF CALIFORNIA   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

BIPYRIDINIUM; BIS 4 PHENYLENE 34 CROWN 10; MACROCYCLIC COMPOUND; PYRIDINIUM DERIVATIVE; ROTAXANE; UNCLASSIFIED DRUG;

ARTICLE; BINDING KINETICS; CHEMICAL BINDING; CHEMICAL REACTION KINETICS; ENERGY ABSORPTION; MATHEMATICAL COMPUTING; STRUCTURE ANALYSIS;

EID: 0032538060     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja9806229     Document Type: Article

References (32)

1. (a) Ashton, P. R.; Belohradsky, M.; Philp, D., Stoddart, J. F. J. Chem. Soc., Chem. Commun. 1993, 1269-1274.
2. (b) Ashton, P. R.; Belohradsky, M.; Philp, D.; Spencer, N.; Stoddart, J. F. J. Chem. Soc., Chem. Commun. 1993, 1274-1277.
3. (c) Amabilino, D. B.; Ashton, P. R.; Belohradsky, M.; Raymo, F. M.; Stoddart, J. F. J. Chem. Soc., Chem. Commun. 1995, 747-750.
4. (d) Amabilino, D. B.; Ashton, P. R.; Belohradsky, M.; Raymo, F. M.; Stoddart, J. F. J. Chem. Soc., Chem. Commun. 1995, 751-753.
5. (e) Ashton, P. R.; Ballardini, R.; Balzani, V.; Belohradsky, M.; Gandolfi, M. T.; Philp, D.; Prodi, L.; Raymo, F. M.; Reddington, M. V.; Spencer, N.; Stoddart, J. F.; Venturi, M.; Williams, D. J. J. Am. Chem. Soc. 1996, 118, 4931-4951.
6. (f) Asakawa, M.; Ashton, P. R.; Ballardini, R.; Balzani, V.; Belohradsky, M.; Gandolfi, M. T.; Kocian, O.; Prodi, L.; Raymo, F. M.; Stoddart, J. F.; Venturi, M. J. Am. Chem. Soc. 1997, 119, 302-310.
7. (g) Raymo, F. M.; Stoddart, J. F. Pure Appl. Chem. 1997, 69, 1987-1997.
8. (h) Amabilino, D. B.; Asakawa, M.; Ashton, P. R.; Ballardini, R.; Balzani, V.; Belohradsky, M.; Credi, A.; Higuchi, M.; Raymo, F. M.; Shimizu, T.; Stoddart, J. F., Venturi, M.; Yase, K. New J. Chem. 1998, 959-972.
9. (a) Lindsey, J. S. New J. Chem. 1991, 15, 153-180.
10. (b) Whitesides, G. M.; Mathias, J. P.; Seto, C. T. Science 1991, 254, 1312-1319.
11. (c) Whitesides, G. M.; Simanek, E. E.; Mathias, J. P.; Seto, C. T.; Chin, D. N.; Mammen, M.; Gordon, D. M. Acc. Chem. Res. 1995, 28, 37-44.
12. (d) Lawrence, D. S.; Jiang, T.; Levett, M. Chem. Rev. 1995, 95, 2229-2260.
13. (e) Raymo, F. M.; Stoddart, J. F. Curr. Opin. Colloid Interface Sci. 1996, 1, 116-126.
14. (f) Philp, D.; Stoddart J. F. Angew. Chem., Int. Ed. Engl. 1996, 35, 1154-1196.
15. (g) Fyfe, M. C. T.; Stoddart, J. F. Acc. Chem. Res. 1997, 30, 393-401.
16. (e) Gillard, R. E.; Raymo, F. M.; Stoddart, J. F. Chem. Eur. J. 1997, 3, 1933-1940.
17. (h) Raymo, F. M.; Stoddart, J. F. Curr. Opin. Colloid Interface Sci. 1998, 3, 150-159.
18. (a) Dietrich-Buchecker, C. O.; Sauvage J.-P. Bioorg. Chem. Front. 1991, 2, 195-248.
19. (b) Gibson, H. W.; Marand, H. Adv. Mater. 1993, 5, 11-21.
20. (c) Chambron, J. C.; Dietrich-Buchecker, C. O.; Sauvage, J.-P. Top. Curr. Chem. 1993, 165, 131-162.
21. (d) Gibson, H. W.; Bheda, M. C.; Engen, P. T. Prog. Polym. Sci. 1994, 19, 843-945.
22. (e) Amabilino, D. B.; Parsons, I. W.; Stoddart, J. F. Trends Polym. Sci. 1994, 2, 146-152.
23. (f) Amabilino, D. B.; Stoddart, J. F. Chem. Rev. 1995, 95, 2725-2828.
24. (g) Raymo, F. M.; Stoddart, J. F. Trends Polym. Sci. 1996, 4, 208-211.
25. (h) Belohradsky, M.; Raymo, F. M.; Stoddart, J. F. Collect. Czech. Chem. Commun. 1996, 61, 1-43.
26. (i) Belohradsky, M.; Raymo, F. M.; Stoddart, J. F. Collect. Czech. Chem. Commun. 1997, 62, 527-557.
27. Mahamadi, F.; Richards, N. G. K.; Guida, W. C.; Liskamp, R.; Lipton, M.; Caufield, D.; Chang, G.; Hendrickson, T.; Still, W. C. J. Comput. Chem. 1990, 11, 440-467.
28. Polak, E.; Ribiere, G. Rev. Fr. Inf. Rech. Oper. 1969, 16-R1, 35-43.
29. Weiner, S. J.; Kollman, P. A.; Case, D. A.; Singh, V. C.; Ghio, C.; Alagona, G.; Profeta, S., Jr; Weiner, P. J. Am. Chem. Soc. 1984, 106, 765-784.
30. Still, W. C.; Tempczyk, A.; Hawley, R. C.; Hendrickson, T. J. Am. Chem. Soc. 1990, 112, 6127-6129.
31. The geometry adopted by the BPP34C10 macrocycle in the solid state was employed. For the X-ray crystal structure of BPP34C10, see: Allwood, B. L.; Spencer, N.; Shariari-Zavareh, H.; Stoddart, J. F.; Williams, D. J. J. Chem. Soc., Chem. Commun. 1987, 1061-1064.
32. -1.