The mechanism of formation of amide-based interlocked compounds: Prediction of a new rotaxane-forming motif

Chemistry - A European Journal

Volumn 10, Issue 20, 2004, Pages 4960-4969

  Leigh, David A ^a   Venturini, Alessandro ^b   Wilson, Andrew J ^a   Wong, Jenny K Y ^a   Zerbetto, Francesco ^c  

^a UNIVERSITY OF EDINBURGH   (United Kingdom)

^b CNR   (Italy)

^c UNIVERSITY OF BOLOGNA   (Italy)

Author keywords

Catenanes; Molecular modeling; Reaction mechanisms; Rotaxanes; Self assembly

Indexed keywords

HYDROGEN BONDS; MOLECULAR STRUCTURE; OLIGOMERS; REACTION KINETICS; SYNTHESIS (CHEMICAL); X RAY CRYSTALLOGRAPHY;

GAS PHASES; MOECULAR MODELING; REAGENT SYSTEMS; SUPRAMOLECULAR INTERACTIONS;

SUPRAMOLECULAR CHEMISTRY;

AMIDE; CATENANE; OLIGOMER; ROTAXANE;

ARTICLE; CHEMICAL REACTION; ENERGY; HYDROGEN BOND; MOLECULAR INTERACTION; MOLECULAR MODEL; PREDICTION; SYNTHESIS; X RAY CRYSTALLOGRAPHY;

EID: 7044226494     PISSN: 09476539     EISSN: None     Source Type: Journal    
DOI: 10.1002/chem.200305662     Document Type: Article

References (60)

1. C. A. Hunter, J. Am. Chem. Soc. 1992, 114, 5303-5311.
2. F. Vögtle, S. Meier, R. Hoss, Angew. Chem. 1992, 104, 1628-1631; Angew. Chem. Int. Ed. Engl. 1992, 31, 1619-1622.
3. F. Vögtle, S. Meier, R. Hoss, Angew. Chem. 1992, 104, 1628-1631; Angew. Chem. Int. Ed. Engl. 1992, 31, 1619-1622.
4. S. Ottens-Hildebrandt, S. Meier, W. Schmidt, F. Vögtle, Angew. Chem. 1994, 106, 1818-1821; Angew. Chem. Int. Ed. Engl. 1994, 33, 1767-1770.
5. S. Ottens-Hildebrandt, S. Meier, W. Schmidt, F. Vögtle, Angew. Chem. 1994, 106, 1818-1821; Angew. Chem. Int. Ed. Engl. 1994, 33, 1767-1770.
6. S. Ottens-Hildebrandt, M. Nieger, K. Rissanen, J. Rouvinen, S. Meier, G. Harder, F. Vögtle, J. Chem. Soc. Chem. Commun. 1995, 777-778.
7. F. Vögtle, R. Jäger, M. Handel, S. Ottens-Hildebrandt, Pure Appl. Chem. 1996, 68, 225-232.
8. S. Baumann, R. Jäger, F. Ahuis, B. Kray, F. Vögtle, Liebigs Ann./Recl. 1997, 761-766.
9. F. Vögtle, O. Safarowsky, C. Heim, A. Affeld, O. Braun, A. Mohry, Pure Appl. Chem. 1999, 71, 247-251.
10. A. Andrievsky, F. Ahuis, J. L. Sessler, F. Vögtle, D. Gudat, M. Moini, J. Am. Chem. Soc. 1998, 120, 9712-9713.
11. O. Safarowsky, E. Vogel, F. Vögtle, Eur. J. Org. Chem. 2000, 499-505.
12. F. Schwanke, O. Safarowsky, C. Heim, G. Silva, F. Vögtle, Helv. Chim. Acta 2000, 83, 3279-3290.
13. A. G. Johnston, D. A. Leigh, R. J. Pritchard, M. D. Deegan, Angew. Chem. 1995, 107, 1324-1327; Angew. Chem. Int. Ed. Engl. 1995, 34, 1209-1212.
14. A. G. Johnston, D. A. Leigh, R. J. Pritchard, M. D. Deegan, Angew. Chem. 1995, 107, 1324-1327; Angew. Chem. Int. Ed. Engl. 1995, 34, 1209-1212.
15. A. G. Johnston, D. A. Leigh, L. Nezhat, J. P. Smart, M. D. Deegan, Angew. Chem. 1995, 107, 1327-1331; Angew. Chem. Int. Ed. Engl. 1995, 34, 1212-1216.
16. A. G. Johnston, D. A. Leigh, L. Nezhat, J. P. Smart, M. D. Deegan, Angew. Chem. 1995, 107, 1327-1331; Angew. Chem. Int. Ed. Engl. 1995, 34, 1212-1216.
17. D. A. Leigh, K. Moody, J. P. Smart, K. J. Watson, A. M. Z. Slawin, Angew. Chem. 1996, 108, 326-331; Angew. Chem. Int. Ed. Engl. 1996, 35, 306-310.
18. D. A. Leigh, K. Moody, J. P. Smart, K. J. Watson, A. M. Z. Slawin, Angew. Chem. 1996, 108, 326-331; Angew. Chem. Int. Ed. Engl. 1996, 35, 306-310.
19. D. A. Leigh, A. Murphy, J. P. Smart, M. S. Deleuze, F. Zerbetto, J. Am. Chem. Soc. 1998, 120, 6458-6467.
20. M. S. Deleuze, D. A. Leigh, F. Zerbetto, J. Am. Chem. Soc. 1999, 121, 2364-2379.
21. T. J. Kidd, D. A. Leigh, A. J. Wilson, J. Am. Chem. Soc. 1999, 121, 1599-1600.
22. N. Watanabe, Y. Furusho, N. Kihara, T. Takata, K. Kinbara, K. Saigo, Chem. Lett. 1999, 915-916.
23. Y. Furusho, J. Shoji, N. Watanabe, N. Kihara, T. Adachi, T. Takata, Bull. Chem. Soc. Jpn. 2001, 74, 139-147.
24. N. Watanabe, N. Kihara, T. Takata, Org. Lett. 2001, 3, 3519-3522.
25. N. Watanabe, Y. Furusho, N. Kihara, T. Takata, K. Kinbara, K. Saigo, Bull. Chem. Soc. Jpn. 2001, 74, 149-155.
26. F. J. Carver, C. A. Hunter, R. J. Shannon, J. Chem. Soc. Chem. Commun. 1994, 1277-1280.
27. C. A. Fustin, C. Bailly, G. J. Clarkson, P. De Groote, T. H. Galow, D. A. Leigh, D. Robertson, A. M. Z. Slawin, J. K. Y. Wong, J. Am. Chem. Soc. 2003, 125, 2200-2207.
28. D. A. Leigh, J. K. Y. Wong, F. Dehez, F. Zerbetto, Nature 2003, 424, 174-179.
29. O. Safarowsky, M. Nieger, R. Fröhlich, F. Vögtle, Angew. Chem. 2000, 112, 1699-1701; Angew. Chem. Int. Ed. 2000, 39, 1616-1618.
30. O. Safarowsky, M. Nieger, R. Fröhlich, F. Vögtle, Angew. Chem. 2000, 112, 1699-1701; Angew. Chem. Int. Ed. 2000, 39, 1616-1618.
31. J. Recker, F. Vögtle, J. Inclusion Phenom. Macrocyclic Chem. 2001, 41, 3-5.
32. F. Vögtle, A. Hünten, E. Vogel, S. Buschbeck, O. Safarowsky, J. Recker, A. H. Parham, M. Knott, W. M. Müller, U. Müller, Y. Okamoto, T. Kubota, W. Lindner, E. Francotte, S. Grimme, Angew. Chem. 2001, 113, 2534-2537; Angew. Chem. Int. Ed. 2001, 40, 2468-2471.
33. F. Vögtle, A. Hünten, E. Vogel, S. Buschbeck, O. Safarowsky, J. Recker, A. H. Parham, M. Knott, W. M. Müller, U. Müller, Y. Okamoto, T. Kubota, W. Lindner, E. Francotte, S. Grimme, Angew. Chem. 2001, 113, 2534-2537; Angew. Chem. Int. Ed. 2001, 40, 2468-2471.
34. A. G. Johnston, D. A. Leigh, A. Murphy, J. P. Smart, M. D. Deegan, J. Am. Chem. Soc. 1996, 118, 10662-10663.
35. D. A. Leigh, A. Murphy, J. P. Smart, A. M. Z. Slawin, Angew. Chem. 1997, 109, 752-756; Angew. Chem. Int. Ed. Engl. 1997, 36, 728-732.
36. D. A. Leigh, A. Murphy, J. P. Smart, A. M. Z. Slawin, Angew. Chem. 1997, 109, 752-756; Angew. Chem. Int. Ed. Engl. 1997, 36, 728-732.
37. W. Clegg, C. Gimenez-Saiz, D. A. Leigh, A. Murphy, A. M. Z. Slawin, S. J. Teat, J. Am. Chem. Soc. 1999, 121, 4124-4129.
38. G. Brancato, F. Coutrot, D. A. Leigh, A. Murphy, J. K. Y. Wong, F. Zerbetto, Proc. Natl. Acad. Sci. USA 2002, 99, 4967-4971.
39. T. Da Ros, D. M. Guldi, A. Farran Morales, D. A. Leigh, M. Prato, R. Turco, Org. Lett. 2003, 5, 689-691.
40. F. G. Gatti, D. A. Leigh, S. A. Nepogodiev, A. M. Z. Slawin, S. J. Teat, J. K. Y. Wong, J. Am. Chem. Soc. 2001, 123, 5983-5989.
41. F. G. Gatti, S. Leòn, J. K. Y. Wong, G. Bottari, A. Altieri, M. A. Farran Morales, S. J. Teat, C. Frochot, D. A. Leigh, A. M. Brouwer, F. Zerbetto, Proc. Natl. Acad. Sci. USA 2003, 100, 10-14.
42. A. Altieri, G. Bottari, F. Dehez, D. A. Leigh, J. K. Y. Wong, F. Zerbetto, Angew. Chem. 2003, 115, 2398-2402; Angew. Chem. Int. Ed. 2003, 42, 2296-2300.
43. A. Altieri, G. Bottari, F. Dehez, D. A. Leigh, J. K. Y. Wong, F. Zerbetto, Angew. Chem. 2003, 115, 2398-2402; Angew. Chem. Int. Ed. 2003, 42, 2296-2300.
44. V. Bermudez, N. Capron, T. Gase, F. G. Gatti, F. Kajzar, D. A. Leigh, F. Zerbetto, S. W. Zhang, Nature 2000, 406, 608-611.
45. H. Adams, F. J. Carver, C. A. Hunter, J. Chem. Soc. Chem. Commun. 1995, 809-810.
46. A. Mohry, F. Vögtle, M. Nieger, H. Hupfer, Chirality 2000, 12, 76-83.
47. Q. Y. Li, E. Vogel, A. H. Parham, M. Nieger, M. Boite, R. Fröhlich, P. Saarenketo, K. Rissanen, F. Vögtle, Eur. J. Org. Chem. 2001, 4041-4049.
48. M. Asakawa, G. Brancato, M. Fanti, D. A. Leigh, T. Shimizu, A. M. Z. Slawin, J. K. Y. Wong, F. Zerbetto, S. W. Zhang, J. Am. Chem. Soc. 2002, 124, 2939-2950.
49. F. Biscarini, M. Cavallini, D. A. Leigh, S. Leon, S. J. Teat, J. K. Y. Wong, F. Zerbetto, J. Am. Chem. Soc. 2002, 124, 225-233.
50. M. H. Abraham, Chem. Soc. Rev. 1993, 22, 73-83.
51. C. Seel, A. H. Parham, O. Safarowsky, G. M. Hubner, F. Vögtle, J. Org. Chem. 1999, 64, 7236-7242.
52. E. Wasserman, J. Am. Chem. Soc. 1960, 82, 4433-4434.
53. H. L. Frisch, E. Wasserman, J. Am. Chem. Soc. 1961, 83, 3789-3795.
54. F. Mohamadi, N. G. J. Richards, W. C. Guida, R. Liskamp, M. Lipton, C. Caufield, G. Chang, T. Hendrickson, W. C. Still, J. Comput. Chem. 1990, 11, 440-467.
55. N. L. Allinger, Y. H. Yuh, J. H. Lii, J. Am. Chem. Soc. 1989, 111, 8551-8582.
56. M. Cavallini, R. Lazzaroni, R. Zamboni, F. Biscarini, D. Timpel, F. Zerbetto, G. J. Clarkson, D. A Leigh, J. Phys. Chem. B 2001, 105, 10826-10830.
57. W. C. Still, A. Tempczyk, R. C. Hawley, T. F. Hendrickson, J. Am. Chem. Soc. 1990, 112, 6127-6129.
58. W. Hasel, T. F. Hendrickson, W. C. Still, Tetrahedron Comput. Methodol. 1988, 1, 103.
59. D. Qiu, P. S. Shenkin, F. P. Hollinger, W. C. Still, J. Phys. Chem. A 1997, 101, 3005-3014.
60. Many other factors (e.g., solubility of the reagents, products and intermediates, reaction conditions, efficacy of purification methods) can also affect reaction yield.