Rotaxane or pseudorotaxane? Effects of small structural variations on the deslipping kinetics of rotaxanes with stopper groups of intermediate size

European Journal of Organic Chemistry

Volumn , Issue 15, 2001, Pages 2877-2890

  Affeld, Ansgar ^a   Hühner, Gosia M ^a   Seel, Christian ^a   Schalley, Christoph A ^a  

^a UNIVERSITY OF BONN   (Germany)

Author keywords

Arrhenius kinetics; Eyring theory; Rotaxanes; Slipping synthesis; Supramolecular chemistry; Template synthesis

Indexed keywords

PHENOL DERIVATIVE; ROTAXANE; SULFONAMIDE; UREA;

ARTICLE; CHEMICAL REACTION KINETICS; ENTROPY; HYDROGEN BOND; MOLECULAR RECOGNITION; PROTON NUCLEAR MAGNETIC RESONANCE; SYNTHESIS;

EID: 0034890681     PISSN: 1434193X     EISSN: None     Source Type: Journal    
DOI: 10.1002/1099-0690(200108)2001:15<2877::AID-EJOC2877>3.0.CO;2-R     Document Type: Article

References (147)

1. [1a] G. Schill, Catenanes, Rotaxanes and Knots, Academic Press, New York, 1971. -
2. [1b] Molecular Catalanes, Rotaxanes, and Knots (Eds.: J. P. Sauvage, C. Dietrich-Buchecker), Wiley-VCH, Weinheim, 1999.
3. For a recent example of a knot synthesis based on nonionic template effects, see: O. Safarowsky, M. Nieger, R. Fröhlich, F. Vögtle, Angew. Chem. 2000, 112, 1699-1701;
4. Angew. Chem. Int. Ed. 2000, 39, 1616-1618.
5. For reviews, see: [3a] C. O. Dietrich-Buchecker, J.-P. Sauvage, Chem. Rev. 1987, 87, 795-810. -
6. [3b] J.-P. Sauvage, Acc. Chem. Res. 1990, 23, 319-327. -
7. [3c] S. Anderson, H. L. Anderson, J. K. M. Sanders, Acc. Chem. Res. 1993, 26, 469-475. -
8. [3d] R. Hoss, F. Vöstle, Angew. Chem. 1994, 106, 389-398;
9. Angew. Chem. Int. Ed. Engl. 1994, 33, 375-384. -
10. [3e] J.-C. Chambron, C. O. Dietrich-Buchecker, V. Heitz, J.-F. Nierengarten, J.-P. Sauvage, C. Pascard, J. Guilhem, Pure Appl. Chem. 1995, 67, 233-240. -
11. [3f] R. Jäger, F. Vögtle, Angew. Chem. 1997, 109, 966-980;
12. Angew. Chem. Int. Ed. Engl. 1997, 36, 930-944. -
13. [3g] S. A. Nepogodiev, J. F. Stoddart, Chem. Rev. 1998, 98, 1959-1976. -
14. [3h] F. M. Raymo, J. F. Stoddart, Chem. Rev. 1999, 99, 1043-1063.
15. [4a] D. E. Adams, E. M. Shekhtman, E. L. Zechiedrich, M. B. Schmid, N. R. Cozzarelli, Cell 1992, 71, 277-288. -
16. [4b] J. Chen, C. A. Rauch, J. H. White, P. T. Englund, N. R. Cozzarelli, Cell 1995, 80, 61-69. -
17. For a review, see: [4c] N. C. Seeman, Angew. Chem. 1998, 110, 3408-3428;
18. Angew. Chem. Int. Ed. 1998, 37, 3220-3238.
19. [5a] C. Liang, K. Mislow, J. Am. Chem. Soc. 1994, 116, 11189-11190. -
20. [5b] F. Takusasawa, S. Kamitori, J. Am. Chem. Soc. 1996, 118, 8945-8946.
21. [6a] P. D. Boyer, Angew. Chem. 1998, 110, 2424-2436;
22. Angew. Chem. Int. Ed. 1998, 37, 2296-2307. -
23. [6b] J. E. Walker, Angew. Chem. 1998, 110, 2438-2450;
24. Angew. Chem. Int. Ed. 1998, 37, 2308-2319.
25. R. M. Macnab, S.-I. Aizawa, Annu. Rev. Biophys. Bioeng. 1984, 13, 51-83.
26. [8a] D. K. Mitchell, J.-P. Sauvage, Angew. Chem. 1988, 100, 985-987;
27. Angew. Chem. Int. Ed. Engl. 1988, 27, 930-932. -
28. [8b] Y. Kaida, Y. Okamoto, J.-C. Chambron, D. K. Mitchell, J.-P. Sauvage, Tetrahedron Lett. 1993, 34, 1019-1023. -
29. [8c] P. R. Ashton A. S. Reder, N. Spencer, J. F. Stoddart, J. Am. Chem. Soc. 1993, 115, 5286-5287. -
30. [8d] C. Yamamoto, Y. Okamoto, T. Schmidt, R. Jäger, F. Vögtle, J. Am. Chem. Soc. 1997, 119, 10547-10548. -
31. [8e] P. R. Ashton, J. A. Bravo, F. M. Raymo, J. F. Stoddart, A. J. P. White, D. J. Williams, Eur. J. Org. Chem. 1999, 899-908. -
32. [8f] R. Schmieder, G. Hübner, C. Seel, F. Vögtle, Angew. Chem. 1999, 111, 3741-3743;
33. Angew. Chem. Int. Ed. 1999, 38, 3528-3530. -
34. [8g] C. Reuter, A. Mohry, A. Sobanski, F. Vögtle, Chem. Eur. J. in press. -
35. For a review, see: [8h] J.-C. Chambron, C. O. Dietrich-Buchecker, J. P. Sauvage, Top. Curr. Chem. 1993, 165, 131-162.
36. [9a] K. E. Drexler, Annu. Rev. Biophys. Biomol. Struct. 1994, 23, 377-405. -
37. [9b] V. Balzani, M. Gómez-López, J. F. Stoddart, Acc. Chem. Res. 1998, 31, 405-413. -
38. [9c] J.-P. Sauvage, Acc. Chem. Res. 1998, 31, 611-619.-
39. [9d] J.-P. Collin, P. Gaviña, V. Heitz, J.-P. Sauvage, Eur. J. Inorg. Chem. 1998, 1-14. -
40. [9e] Z. Asfari, J. Vicens, J. Incl. Phenom. Macrocyc. Chem. 2000, 36, 103-118. -
41. [9f] V. Balzani, A. Credi, F. M. Raymo, J. F. Stoddart, Angew. Chem. 2000, 112, 3484-3530;
42. Angew. Chem. Int. Ed. 2000, 39, 3348-3391. -
43. [9g] C. A. Schalley, K. Beizai, F. Vögtle, Acc. Chem. Res. submitted.
44. [10a] D. J. Cárdenas, P. Gaviñas, J.-P. Sauvage, Chem. Commun. 1996, 1915-1916. -
45. [10b] D. B. Amabilino, C. O. Dietrich-Buchecker, J.-P. Sauvage, J. Am. Chem. Soc. 1996, 118, 3285-3286. -
46. [10c] D. J. Cárdenas, P. Gaviñas, J.-P. Sauvage, J. Am. Chem. Soc. 1997, 119, 2656-2664. -
47. For a review, see: [10d] J.-C. Chambron, S. Chardon-Noblat, A. Harriman, V. Heitz, J.-P. Sauvage, Pure Appl. Chem. 1993, 65, 2343-2349.
48. F. Diederich, L. Echegoyen, M. Gómez-López, R. Kessinger, J. F. Stoddart, J. Chem. Soc., Perkin Trans. 2 1999, 1577-1586.
49. F. Vögtle, W. M. Müller, U. Müller, M. Bauer, K. Rissanen, Angew. Chem. 1993, 105, 1356-1358;
50. Angew. Chem. Int. Ed. Engl. 1993, 32, 1295-1297.
51. S. S. Zhu, P. J. Carroll, T. M. Swager, J. Am. Chem. Soc. 1996, 118, 8713-8714.
52. [14a] A Credi, V. Balzani, S. J. Langford, J. F. Stoddart, J. Am. Chem. Soc. 1997, 119, 2679-2681. -
53. [14b] M. Asakawa, P. R. Ashton, V. Balzani, A. Credi, G. Mattersteig, O. A. Matthews, M. Montalti, N. Spencer, J. F. Stoddart, M. Venturi, Chem. Eur. J. 1997, 3, 1992-1996.
54. For a computational study of the size requirements of the deslipping process, see: F. M. Raymo, K. N. Houk, J. F. Stoddart, J. Am. Chem. Soc. 1998, 120, 9318-9322.
55. [16a] G. Hübner, G. Nachtsheim, Q.-Y. Li, C. Seel, F. Vögtle, Angew. Chem. 2000, 112, 1315-1318;
56. Angew. Chem. Int. Ed. 2000, 39, 1269-1272. -
57. Also, see: [16b] H. W. Gibson, S. Liu, P. Lecavalier, C. Wu, Y. X. Shen, J. Am. Chem. Soc. 1995, 117, 852-874. -
58. [16c] C. Heim, Ph. D. Thesis, Universität Bonn, 1998. -
59. [16d] C. Heim, A. Affeld, M. Nieger, F. Vögtle, Helv. Chim. Acta 1999, 82, 746-759.
60. [17a] P. R. Ashton, R. Ballardini, V. Balzani, M. Blohradsky, M. T. Gandolfi, D. Philp, L. Prodi, F. M. Raymo, M. V. Reddington, N. Spencer, J. F. Stoddart, M. Venturi, D. J. Williams, J. Am. Chem. Soc. 1996, 118, 4931-4951. -
61. [17b] M. Asakawa, P. R. Ashton, R. Ballardini, V. Balzani, M. Belohradsky, M. T. Gandolfi, O. Kocian, L. Prodi, F. M. Raymo, J. F. Stoddart, M. Venturi, J. Am. Chem. Soc. 1997, 119, 302-310. -
62. [17c] P. R. Ashton, I. Baxter, M. C. T. Fyfe, F. M. Raymo, N. Spencer, J. F. Stoddart, A. J. P. White, D. J. Williams, J. Am. Chem. Soc. 1998, 120, 2297-2307.
63. For a study of binding constants of the pseudorotaxane axles in the corresponding wheels, see: [18a] P. R. Ashton, D. Philp, M. V. Reddington, A. M. Z. Slawin, N. Spencer, J. F. Stoddart, D. J. Williams, J. Chem. Soc., Chem. Commun. 1991, 1680-1682. -
64. For some recent publications on pseudorotaxanes, see: [18b] P. R. Ashton, M. C. T. Fyfe, M.-V. Martínez-Díaz, S. Menzer, C. Schiavo, J. F. Stoddart, A. J. P. White, D. J. Williams, Chem. Eur. J. 1998, 4, 1523-1534. -
65. [18c] C. Gong, H. W. Gibson, Angew. Chem. 1998, 110, 323-327;
66. Angew. Chem. Int. Ed. 1998, 37, 310-314. -
67. [18d] P. R. Ashton, I. W. Parsons, F. M. Raymo, J. F. Stoddart, A. J. P. White, D. J. Williams, R. Wolf, Angew. Chem. 1998, 110, 2016-2019;
68. Angew. Chem. Int. Ed. 1998, 37, 1913-1916.
69. [19a] I. T. Harrison, J. Chem. Soc., Chem. Commun. 1972, 231-232. -
70. [19b] I. T. Harrison, J. Chem. Soc., Perkin Trans. 1 1974, 301-304. -
71. [19c] G. Agam, D. Graiver, A. Zilkha, J. Am. Chem. Soc. 1976, 98, 5206-5214. -
72. [19d] G. Agam, A. Zilkha, J. Am. Chem. Soc. 1976, 98, 5214-5216. -
73. [19e] G. Schill, W. Beckmann, N. Schweickert, H. Fritz, Chem. Ber. 1986, 119, 2647-2655. -
74. [19f] P. R. Ashton, M. Belohradsky, D. Philp, J. F. Stoddart, J. Chem. Soc., Chem. Commun. 1993, 1269-1274. -
75. [19g] P. R. Ashton, M. Belohradský, D. Philp, N. Spencer, J. F. Stoddart, J. Chem. Soc., Chem. Commun. 1993, 1274-1277. -
76. [19h] D. H. Macartney, J. Chem. Soc., Perkin Trans. 2 1996, 2775-2778. -
77. [19i] M. Händel, M. Plevoets, S. Gestermann, F. Vögtle, Angew. Chem. 1997, 109, 1248-1250;
78. Angew. Chem. Int. Ed. Engl. 1997, 36, 1199-1201. -
79. [19j] M. C. T. Fyfe, F. M. Raymo, J. F. Stoddart, in: Stimulating Concepts in Chemistry (Eds.: J. F. Stoddart, F. Vögtle), Wiley-VCH, Weinheim, 2000, p. 211.
80. For a few examples, see: [20a] P. L. Anelli, N. Spencer, J. F. Stoddart, J. Am. Chem. Soc. 1991, 113, 5131-5133. -
81. [20b] R. A. Bissell, E. Córdova, A. E. Kaifer, Nature 1994, 369, 133-137. -
82. [20c] D. B. Amabilino, P.-L. Anelli, P. R. Ashton, G. R. Brown, E. Córdova, L. A. Godínez, W. Hayes, A. E. Kaifer, D. Philp, A. M. Z. Slawin, N. Spencer, J. F. Stoddart, M. S. Tolley, D. J. Williams, J. Am. Chem. Soc. 1995, 117, 11142-11170. -
83. [20d] A. C. Benniston, A. Harriman, V. M. Lynch, J. Am. Chem. Soc. 1995, 117, 5275-5291. -
84. [20e] A. S. Lane, D. A. Leigh, A. Murphy, J. Am. Chem. Soc. 1997, 119, 11092-11093. -
85. [20f] J.-P. Collin, P. Gaviña, J.-P. Sauvage, New J. Chem. 1997, 21, 525-528. -
86. [20g] H. Murakami, A. Kawabuchi, K. Kotoo, M. Kunitake, M. Nakashima, J. Am. Chem. Soc. 1997, 119, 7605-7606. -
87. [20h] D. A. Leigh, A. Troisi, F. Zerbetto, Angew. Chem. 2000, 112, 358-361;
88. Angew. Chem. Int. Ed 2000, 39, 350-353.
89. For a small selection of references, see: [21a] A. Livoreil, C. O. Dietrich-Buchecker, J.-P. Sauvage, J. Am. Chem. Soc. 1994, 116, 9399-9400. -
90. [21b] A. G. Johnston, D. A. Leigh, R. J. Pritchard, M. D. Deegan, Angew. Chem. 1995, 107, 1324-1327;
91. Angew. Chem. Int. Ed. Engl. 1995, 34, 1209-1212. -
92. [21c] D. A. Leigh, K. Moody, J. P. Smart, K. J. Watson, A. M. Z. Slawin, Angew. Chem. 1996, 108, 326-331;
93. Angew. Chem. Int. Ed. Engl. 1996, 35, 306-310. -
94. [21d] F. Vögtle, T. Dünnwald, T. Schmidt, Acc. Chem. Res. 1996, 29, 451-460. -
95. [21e] A. Livoreil, J.-P. Sauvage, N. Armaroli, V. Balzani, L. Flamigni, B. Ventura, J. Am. Chem. Soc. 1997, 119, 12114-12124. -
96. [21f] M. C. T. Fyfe, P. T. Glink, S. Menzer, J. F. Stoddart, A. J. P. White, D. J. Williams, Angew. Chem. 1997, 109, 2158-2160;
97. Angew. Chem. Int. Ed. Engl. 1997, 36, 2068-2070. -
98. [21g] M. S. Deleuze, D. A. Leigh, F. Zerbetto, J. Am. Chem. Soc. 1999, 121, 2364-2379.
99. C. Seel, A. H. Parham, O. Safarowsky, G. M. Hübner, F. Vögtle, J. Org. Chem. 1999, 64, 7236-7242.
100. [23a] C. Reuter, C. Seel, M. Nieger, F. Vögtle, Helv. Chim. Acta 2000, 83, 630-640. -
101. [23b] A. Mohry, F. Vögtle, M. Nieger, H. Hupfer, Chirality 2000, 12, 76-83.
102. Rot10@2′ and Rot11@2′ both bear an additional tert-butyl group at the periphery of the wheel. We believe that it does not significantly alter the deslipping kinetics. If so, one would expect some additional steric hindrance, which, however, is not in line with the results in Table 1.
103. B. Sunners, L. H. Piette, W. G. Schneider, Can. J. Chem. 1960, 38, 681-688.
104. [26a] K. B. Wiberg, K. E. Laidig, J. Am. Chem. Soc. 1987, 109, 5935-5943. -
105. [26b] For a review, see: K. B. Wiberg, C.M. Hadad, C. M. Breneman, K. E. Laidig, M. A. Murcko, T. J. LePage, Science 1991, 252, 1266-1272.
106. C. M. Breneman, L. W. Weber, Can. J. Chem. 1996, 74, 1271-1282.
107. D. A. Leigh, A. Murphy, J. P. Smart, A. M. Z. Slawin, Angew. Chem. 1997, 109, 752-756;
108. Angew. Chem. Int. Ed. Engl. 1997, 36, 728-732.
109. S. Ottens-Hildebrandt, M. Nieger, K. Rissanen, J. Rouvinen, S. Meier, G. Harder, F. Vögtle, J. Chem. Soc., Chem. Commun. 1995, 777-778.
110. A. G. Johnston, D. A. Leigh, L. Nehzat, J. P. Smart, M. D. Deegan, Angew. Chem. 1995, 107, 1327-1331;
111. Angew. Chem. Int. Ed. Engl. 1995, 34, 1202-1216.
112. [31a] Y. Hamuro, S. J. Geib, A. D. Hamilton, Angew. Chem. 1994, 106, 465-467;
113. Angew. Chem. Int. Ed. Engl. 1994, 33, 446-448. -
114. [31b] C. A. Hunter, L. D. Sarson, Angew. Chem. 1994, 106, 2424-2426;
115. Angew. Chem. Int. Ed. Engl. 1994, 33, 2313-2316.
116. [32a] C. A. Hunter, D. H. Purvis, Angew. Chem. 1992, 104, 779-782;
117. Angew. Chem. Int. Ed. Engl. 1992, 31, 792-795. -
118. [32b] V. Berl, I. Huc, R. G. Khoury, M. J. Krische, J.-M. Lehn, Nature 2000, 407, 720-723. -
119. [32c] V. Berl, M. J. Krische, I. Huc, J.-M. Lehn, M. Schmutz, Chem. Eur. J. 2000, 6, 1938-1946.
120. Sybyl force field, Spartan, Wavefunction Inc., 18401 Von Karman Ave., Irvine, CA 92612, USA.
121. [34a] M. Miyaura, T. Yanagi, A. Suzuki, Synth. Commun. 1981, 7, 513-519. -
122. [34b] A. R. Katritzky, S. A. Belyakov, S. A. Henderson, P. J. Steel, J. Org. Chem. 1997, 62, 8215-8217.
123. [35a] J. Heinze, J. Mortensen, K. Müllen, R. Schenk, J. Chem. Soc., Chem. Commun. 1987, 701-703. -
124. [35b] R. Schenk, J. Hucker, H. Hopf, H. J. Raeder, K. Müllen, Angew. Chem. 1989, 101, 942-944;
125. Angew. Chem. Int. Ed. Engl. 1989, 28, 904-906. -
126. [35c] K. Sandros, M. Sundahl, O. Wennerström, U. Norinder, J. Am. Chem. Soc. 1992, 112, 3082-3086.
127. [36a] C. A. Hunter, J. Chem. Soc., Chem. Commun. 1991, 749-751. -
128. [36b] C. A. Hunter, J. Am. Chem. Soc. 1992, 114, 5303-5311. -
129. [36c] F. Vögtle, S. Meier, R. Hoss, Angew. Chem. 1992, 104, 1628-1631;
130. Angew. Chem. Int. Ed. Engl. 1992, 31, 1619-1622.
131. [37a] S. Ottens-Hildebrandt, T. Schmidt, J. Harren, F. Vögtle, Liebigs Ann. 1995, 1855-1860. -
132. [37b] R. Jäger, M. Händel, K. Rissanen, F. Vögtle, Liebigs Ann. 1996, 1201-1207. -
133. [37c] F. Vögtle, R. Jäger, M. Händel, S. Ottens-Hildebrandt, W. Schmidt, Synthesis 1996, 353.
134. [38a] A. Affeld, Ph. D. Thesis, Universität Bonn, 2000. -
135. [38b] A. Hunten, Ph. D. Thesis, Universität Bonn, 2001.
136. [39a] G. M. Hübner, J. Gläser, C. Seel, F. Vögtle, Angew. Chem. 1999, 111, 395-398;
137. Angew. Chem. Int. Ed. 1999, 38, 383-386. -
138. [39b] C. Reuter, W. Wienand, G. M. Hübner, C. Seel, F. Vögtle, Chem. Eur. J. 1999, 5, 2692-2697. -
139. [39c] C. Reuter, F. Vögtle, Org. Lett. 2000, 2, 593-595. -
140. [39d] C. Seel, F. Vögtle, Chem. Eur. J. 2000, 6, 21-24.
141. [40a] S. Ottens-Hildebrandt, S. Meier, W. Schmidt, F. Vögtle, Angew. Chem. 1994, 106, 1818-1821;
142. Angew. Chem. Int. Ed. Engl. 1994, 33, 1767-1770. -
143. [40b] F. Vögtle, M. Händel, S. Meier, S. Ottens-Hildebrandt, F. Ott, T. Schmidt, Liebigs Ann. 1995, 739-743. -
144. [40c] R. Jäger, T. Schmidt, D. Karbach, F. Vögtle, Synlett 1996, 723. -
145. [40d] R. Jäger, S. Baumann, M. Fischer, O. Safarowsky, M. Nieger, F. Vögtle, Liebigs Ann./Recueil 1997, 2269-2273. -
146. [40e] R. Jäger, F. Vögtle, Angew. Chem. 1997, 109, 966-980;
147. Angew. Chem. Int. Ed. Engl. 1997, 36, 930-944.