A new cyclic pseudopeptide composed of (L)-proline and 3-aminobenzoic acid subunits as a ditopic receptor for the simultaneous complexation of cations and anions

Journal of Organic Chemistry

Volumn 64, Issue 26, 1999, Pages 9475-9486

  Kubik, Stefan ^a   Goddard, Richard ^b  

^a HEINRICH HEINE UNIVERSITY   (Germany)

^b MAX PLANCK INSTITUT FÜR KOHLENFORSCHUNG   (Germany)

Author keywords

[No Author keywords available]

Indexed keywords

3 AMINOBENZOIC ACID; PROLINE; PSEUDOPEPTIDE;

AMINO ACID COMPOSITION; ARTICLE; CHEMICAL ANALYSIS; CHEMICAL BINDING; CHEMICAL REACTION; CHEMICAL STRUCTURE; COMPLEX FORMATION; RECEPTOR BINDING; X RAY CRYSTALLOGRAPHY;

EID: 0033601288     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo991087d     Document Type: Article

References (77)

1. Lehn, J.-M. Supramolecular chemistry; VCH: Weinheim, Germany, 1995.
2. Higler, I.; Timmermann, P.; Verboom, W.; Reinhoudt, D. N. Eur. J. Org. Chem. 1998, 2689-2702.
3. Ozeki, E.; Kimura, S.; Imanishi, Y. Int. J. Pept. Protein Res. 1989, 34, 111-117. Ishizu, T.; Hirayama, J.; Noguchi, S. Chem. Pharm. Bull. 1994, 42, 1146-1148. Leipert, D.; Nopper, D.; Bauser, M.; Gauglitz, G.; Jung, G. Angew. Chem., Int. Ed. Engl. 1998, 37, 3311-3314.
4. Ozeki, E.; Kimura, S.; Imanishi, Y. Int. J. Pept. Protein Res. 1989, 34, 111-117. Ishizu, T.; Hirayama, J.; Noguchi, S. Chem. Pharm. Bull. 1994, 42, 1146-1148. Leipert, D.; Nopper, D.; Bauser, M.; Gauglitz, G.; Jung, G. Angew. Chem., Int. Ed. Engl. 1998, 37, 3311-3314.
5. Ozeki, E.; Kimura, S.; Imanishi, Y. Int. J. Pept. Protein Res. 1989, 34, 111-117. Ishizu, T.; Hirayama, J.; Noguchi, S. Chem. Pharm. Bull. 1994, 42, 1146-1148. Leipert, D.; Nopper, D.; Bauser, M.; Gauglitz, G.; Jung, G. Angew. Chem., Int. Ed. Engl. 1998, 37, 3311-3314.
6. Ghadiri, M. R.; Granja, J. R.; Milligan, R. A.; McRee, D. E.; Khazanovich, N. Nature 1993, 366, 324-327. Granja, J. R.; Ghadiri, M. R. J. Am. Chem. Soc. 1994, 116, 10785-10786. Ghadiri, R. M. Adv. Mater. 1995, 7, 675-677. Hartgerink, J. D.; Granja, J. R.; Milligan, R. A.; Ghadiri, M. R. J. Am. Chem. Soc. 1996, 118, 43-50. The natural potassium receptor valinomycin, a cyclic dodecadepsipeptide, is composed of (D)-hydroxycarboxylic acids and (L)-amino acids.
7. Ghadiri, M. R.; Granja, J. R.; Milligan, R. A.; McRee, D. E.; Khazanovich, N. Nature 1993, 366, 324-327. Granja, J. R.; Ghadiri, M. R. J. Am. Chem. Soc. 1994, 116, 10785-10786. Ghadiri, R. M. Adv. Mater. 1995, 7, 675-677. Hartgerink, J. D.; Granja, J. R.; Milligan, R. A.; Ghadiri, M. R. J. Am. Chem. Soc. 1996, 118, 43-50. The natural potassium receptor valinomycin, a cyclic dodecadepsipeptide, is composed of (D)-hydroxycarboxylic acids and (L)-amino acids.
8. Ghadiri, M. R.; Granja, J. R.; Milligan, R. A.; McRee, D. E.; Khazanovich, N. Nature 1993, 366, 324-327. Granja, J. R.; Ghadiri, M. R. J. Am. Chem. Soc. 1994, 116, 10785-10786. Ghadiri, R. M. Adv. Mater. 1995, 7, 675-677. Hartgerink, J. D.; Granja, J. R.; Milligan, R. A.; Ghadiri, M. R. J. Am. Chem. Soc. 1996, 118, 43-50. The natural potassium receptor valinomycin, a cyclic dodecadepsipeptide, is composed of (D)-hydroxycarboxylic acids and (L)-amino acids.
9. Ghadiri, M. R.; Granja, J. R.; Milligan, R. A.; McRee, D. E.; Khazanovich, N. Nature 1993, 366, 324-327. Granja, J. R.; Ghadiri, M. R. J. Am. Chem. Soc. 1994, 116, 10785-10786. Ghadiri, R. M. Adv. Mater. 1995, 7, 675-677. Hartgerink, J. D.; Granja, J. R.; Milligan, R. A.; Ghadiri, M. R. J. Am. Chem. Soc. 1996, 118, 43-50. The natural potassium receptor valinomycin, a cyclic dodecadepsipeptide, is composed of (D)-hydroxycarboxylic acids and (L)-amino acids.
10. (a) Bach, A. C., II; Eyermann, C. J.; Gross, J. D.; Bower, M. J.; Harlow, R. L.; Weber, P. C.; DeGrado, W. F. J. Am. Chem. Soc. 1994, 116, 3207-3219.
11. (b) Jackson, S.; DeGrado, W.; Dwivedi, A.; Parthasarathy, A.; Higley, A.; Krywko, J.; Rockwell, A.; Markwalder, J.; Wells, G.; Wexler, R.; Mousa, S.; Harlow, R. J. Am. Chem. Soc. 1994, 116, 3220-3230.
12. (c) Ishida, H.; Suga, M.; Donowaki, K.; Ohkubo, K. J. Org. Chem. 1995, 60, 5374-5375.
13. (d) Ishida, H.; Donowaki, K.; Suga, M.; Shimose, K.; Ohkubo, K. Tetrahedron Lett. 1995, 36, 8987-8990.
14. (e) Bach, A. C., II; Espina, J. R.; Jackson, S. A.; Stouten, P. F. W.; Duke, J. L.; Mousa, S. A.; DeGrado, W. F. J. Am. Chem. Soc. 1996, 118, 293-294.
15. (f) Garcia, M. E.; Gavin, J. A.; Deng, N.; Andrievsky, A. A.; Mallouk, T. E. Tetrahedron Lett. 1996, 37, 8313-8316.
16. (g) Mu, L.; Cheng, J.; Huang, H.; Lu, J.; Hu, X. Synth. Commun. 1998, 28, 3091-3096.
17. (h) Ranganathan, D.; Haridas, V.; Gilardi, R.; Karle, I. L. J. Am. Chem. Soc. 1998, 120, 10793-10800.
18. (i) Ranganathan, D.; Haridas, V.; Karle, I. L. J. Am. Chem. Soc. 1998, 120, 2695-2702.
19. (a) Miyake, H.; Yamashita, T.; Kojima, Y.; Tsukube, H. Tetrahedron Lett. 1995, 36, 7669-7672.
20. (b) Haubner, R.; Schmitt, W.; Hölzemann, G.; Goodman, S. L.; Jonczyk, A.; Kessler, H. J. Am. Chem. Soc. 1996, 118, 7881-7891.
21. (c) Karle, I. L.; Ranganathan, D.; Haridas, V. J. Am. Chem. Soc. 1996, 118, 10916-10917.
22. (d) Albert, D.; Feigel, M. Helv. Chim. Acta 1997, 80, 2168-2181.
23. (e) Ranganathan, D.; Haridas, V.; Madhusudanan, K. P.; Roy, R.; Nagaraj, R.; John, G. B. J. Am. Chem. Soc. 1997, 119, 11578-11584.
24. (f) Karle, I. L.; Ranganathan, D.; Haridas, V. J. Am. Chem. Soc. 1998, 120, 6903-6908.
25. Kubik, S. J. Am. Chem. Soc. 1999, 121, 5846-5855.
26. (a) Araki, K.; Shimizu, H.; Shinkai, S. Chem. Lett. 1993, 205-208.
27. (b) Inokuchi, F.; Araki, K.; Shinkai, S. Chem. Lett. 1994, 1383-1386.
28. (c) Takeshita, M.; Nishio, S.; Shinkai, S. J. Org. Chem. 1994, 59, 4032-4034.
29. (d) Casnati, A.; Jacopozzi, P.; Pochini, A.; Ugozzoli, F.; Cacciapaglia, R.; Mandolini, L.; Ungaro, R. Tetrahedron 1995, 51, 591-598.
30. (e) Arduini, A.; McGregor, W. M.; Paganuzzi, D.; Pochini, A.; Secchi, A.; Ugozzoli, F.; Ungaro, R. J. Chem. Soc., Perkin Trans. 2 1996, 839-846.
31. (f) Magrans, J. O.; Ortiz, A. R.; Molins, M. A.; Lebouille, P. H. P.; Sánchez-Quesada, J.; Prados, P.; Pons, M.; Gago, F.; de Mendoza, J. Angew. Chem., Int. Ed. Engl. 1996, 35, 1712-1715.
32. (g) Arnecke, R.; Böhmer, V.; Cacciapaglia, R.; Dalla Cort, A.; Mandolini, L. Tetrahedron 1997, 53, 4901-4908.
33. (h) Lhotak, P.; Shinkai, S. J. Phys. Org. Chem. 1997, 10, 273-285.
34. For examples of other artificial ditopic receptors that bind ion pairs see: Reetz, M. T.; Niemeyer, C. M.; Harms, K. Angew. Chem., Int. Ed. Engl. 1991, 30, 1474-1476. Arafa, E. A.; Kinnear, K. I.; Lockhart, J. C. J. Chem. Soc., Chem. Commun. 1992, 61-64. Flack, S. S.; Chaumette, J. L.; Kilburn, J. D.; Langley, G. J.; Webster, M. J. Chem. Soc., Chem. Commun. 1993, 399-401. Rudkevich, D. M.; Verboom, W.; Reinhoudt, D. N. J. Org. Chem. 1994, 59, 3683-3686. Rudkevich, D. M.; Brzozka, Z.; Palys, M.; Visser, H. C.; Verboom, W.; Reinhoudt, D. N. Angew. Chem., Int. Ed. Engl. 1994, 33, 467-468. Savage, P. B.; Holmgren, S K.; Gellman, S. H. J. Am. Chem. Soc. 1994, 116, 4069-4070. Rudkevich, D. M.; Mercer-Chalmers, J. D.; Verboom, W.; Ungaro, R.; de Jong, F.; Reinhoudt, D. N. J. Am. Chem. Soc. 1995, 117, 6124-6125. Scheerder, J.; van Duynhoven, J. P. M.; Engbersen, J. F. J.; Reinhoudt, D. N. Angew. Chem., Int. Ed. Engl. 1996, 35, 1090- 1093. Pelizzi, N.; Casnati, A.; Friggeri, A.; Ungaro, R. J. Chem. Soc., Perkin Trans. 2 1998, 1307-1311.
35. For examples of other artificial ditopic receptors that bind ion pairs see: Reetz, M. T.; Niemeyer, C. M.; Harms, K. Angew. Chem., Int. Ed. Engl. 1991, 30, 1474-1476. Arafa, E. A.; Kinnear, K. I.; Lockhart, J. C. J. Chem. Soc., Chem. Commun. 1992, 61-64. Flack, S. S.; Chaumette, J. L.; Kilburn, J. D.; Langley, G. J.; Webster, M. J. Chem. Soc., Chem. Commun. 1993, 399-401. Rudkevich, D. M.; Verboom, W.; Reinhoudt, D. N. J. Org. Chem. 1994, 59, 3683-3686. Rudkevich, D. M.; Brzozka, Z.; Palys, M.; Visser, H. C.; Verboom, W.; Reinhoudt, D. N. Angew. Chem., Int. Ed. Engl. 1994, 33, 467-468. Savage, P. B.; Holmgren, S K.; Gellman, S. H. J. Am. Chem. Soc. 1994, 116, 4069-4070. Rudkevich, D. M.; Mercer-Chalmers, J. D.; Verboom, W.; Ungaro, R.; de Jong, F.; Reinhoudt, D. N. J. Am. Chem. Soc. 1995, 117, 6124-6125. Scheerder, J.; van Duynhoven, J. P. M.; Engbersen, J. F. J.; Reinhoudt, D. N. Angew. Chem., Int. Ed. Engl. 1996, 35, 1090- 1093. Pelizzi, N.; Casnati, A.; Friggeri, A.; Ungaro, R. J. Chem. Soc., Perkin Trans. 2 1998, 1307-1311.
36. For examples of other artificial ditopic receptors that bind ion pairs see: Reetz, M. T.; Niemeyer, C. M.; Harms, K. Angew. Chem., Int. Ed. Engl. 1991, 30, 1474-1476. Arafa, E. A.; Kinnear, K. I.; Lockhart, J. C. J. Chem. Soc., Chem. Commun. 1992, 61-64. Flack, S. S.; Chaumette, J. L.; Kilburn, J. D.; Langley, G. J.; Webster, M. J. Chem. Soc., Chem. Commun. 1993, 399-401. Rudkevich, D. M.; Verboom, W.; Reinhoudt, D. N. J. Org. Chem. 1994, 59, 3683-3686. Rudkevich, D. M.; Brzozka, Z.; Palys, M.; Visser, H. C.; Verboom, W.; Reinhoudt, D. N. Angew. Chem., Int. Ed. Engl. 1994, 33, 467-468. Savage, P. B.; Holmgren, S K.; Gellman, S. H. J. Am. Chem. Soc. 1994, 116, 4069-4070. Rudkevich, D. M.; Mercer-Chalmers, J. D.; Verboom, W.; Ungaro, R.; de Jong, F.; Reinhoudt, D. N. J. Am. Chem. Soc. 1995, 117, 6124-6125. Scheerder, J.; van Duynhoven, J. P. M.; Engbersen, J. F. J.; Reinhoudt, D. N. Angew. Chem., Int. Ed. Engl. 1996, 35, 1090- 1093. Pelizzi, N.; Casnati, A.; Friggeri, A.; Ungaro, R. J. Chem. Soc., Perkin Trans. 2 1998, 1307-1311.
37. For examples of other artificial ditopic receptors that bind ion pairs see: Reetz, M. T.; Niemeyer, C. M.; Harms, K. Angew. Chem., Int. Ed. Engl. 1991, 30, 1474-1476. Arafa, E. A.; Kinnear, K. I.; Lockhart, J. C. J. Chem. Soc., Chem. Commun. 1992, 61-64. Flack, S. S.; Chaumette, J. L.; Kilburn, J. D.; Langley, G. J.; Webster, M. J. Chem. Soc., Chem. Commun. 1993, 399-401. Rudkevich, D. M.; Verboom, W.; Reinhoudt, D. N. J. Org. Chem. 1994, 59, 3683-3686. Rudkevich, D. M.; Brzozka, Z.; Palys, M.; Visser, H. C.; Verboom, W.; Reinhoudt, D. N. Angew. Chem., Int. Ed. Engl. 1994, 33, 467-468. Savage, P. B.; Holmgren, S K.; Gellman, S. H. J. Am. Chem. Soc. 1994, 116, 4069-4070. Rudkevich, D. M.; Mercer-Chalmers, J. D.; Verboom, W.; Ungaro, R.; de Jong, F.; Reinhoudt, D. N. J. Am. Chem. Soc. 1995, 117, 6124-6125. Scheerder, J.; van Duynhoven, J. P. M.; Engbersen, J. F. J.; Reinhoudt, D. N. Angew. Chem., Int. Ed. Engl. 1996, 35, 1090- 1093. Pelizzi, N.; Casnati, A.; Friggeri, A.; Ungaro, R. J. Chem. Soc., Perkin Trans. 2 1998, 1307-1311.
38. For examples of other artificial ditopic receptors that bind ion pairs see: Reetz, M. T.; Niemeyer, C. M.; Harms, K. Angew. Chem., Int. Ed. Engl. 1991, 30, 1474-1476. Arafa, E. A.; Kinnear, K. I.; Lockhart, J. C. J. Chem. Soc., Chem. Commun. 1992, 61-64. Flack, S. S.; Chaumette, J. L.; Kilburn, J. D.; Langley, G. J.; Webster, M. J. Chem. Soc., Chem. Commun. 1993, 399-401. Rudkevich, D. M.; Verboom, W.; Reinhoudt, D. N. J. Org. Chem. 1994, 59, 3683-3686. Rudkevich, D. M.; Brzozka, Z.; Palys, M.; Visser, H. C.; Verboom, W.; Reinhoudt, D. N. Angew. Chem., Int. Ed. Engl. 1994, 33, 467-468. Savage, P. B.; Holmgren, S K.; Gellman, S. H. J. Am. Chem. Soc. 1994, 116, 4069-4070. Rudkevich, D. M.; Mercer-Chalmers, J. D.; Verboom, W.; Ungaro, R.; de Jong, F.; Reinhoudt, D. N. J. Am. Chem. Soc. 1995, 117, 6124-6125. Scheerder, J.; van Duynhoven, J. P. M.; Engbersen, J. F. J.; Reinhoudt, D. N. Angew. Chem., Int. Ed. Engl. 1996, 35, 1090- 1093. Pelizzi, N.; Casnati, A.; Friggeri, A.; Ungaro, R. J. Chem. Soc., Perkin Trans. 2 1998, 1307-1311.
39. For examples of other artificial ditopic receptors that bind ion pairs see: Reetz, M. T.; Niemeyer, C. M.; Harms, K. Angew. Chem., Int. Ed. Engl. 1991, 30, 1474-1476. Arafa, E. A.; Kinnear, K. I.; Lockhart, J. C. J. Chem. Soc., Chem. Commun. 1992, 61-64. Flack, S. S.; Chaumette, J. L.; Kilburn, J. D.; Langley, G. J.; Webster, M. J. Chem. Soc., Chem. Commun. 1993, 399-401. Rudkevich, D. M.; Verboom, W.; Reinhoudt, D. N. J. Org. Chem. 1994, 59, 3683-3686. Rudkevich, D. M.; Brzozka, Z.; Palys, M.; Visser, H. C.; Verboom, W.; Reinhoudt, D. N. Angew. Chem., Int. Ed. Engl. 1994, 33, 467-468. Savage, P. B.; Holmgren, S K.; Gellman, S. H. J. Am. Chem. Soc. 1994, 116, 4069-4070. Rudkevich, D. M.; Mercer-Chalmers, J. D.; Verboom, W.; Ungaro, R.; de Jong, F.; Reinhoudt, D. N. J. Am. Chem. Soc. 1995, 117, 6124-6125. Scheerder, J.; van Duynhoven, J. P. M.; Engbersen, J. F. J.; Reinhoudt, D. N. Angew. Chem., Int. Ed. Engl. 1996, 35, 1090- 1093. Pelizzi, N.; Casnati, A.; Friggeri, A.; Ungaro, R. J. Chem. Soc., Perkin Trans. 2 1998, 1307-1311.
40. For examples of other artificial ditopic receptors that bind ion pairs see: Reetz, M. T.; Niemeyer, C. M.; Harms, K. Angew. Chem., Int. Ed. Engl. 1991, 30, 1474-1476. Arafa, E. A.; Kinnear, K. I.; Lockhart, J. C. J. Chem. Soc., Chem. Commun. 1992, 61-64. Flack, S. S.; Chaumette, J. L.; Kilburn, J. D.; Langley, G. J.; Webster, M. J. Chem. Soc., Chem. Commun. 1993, 399-401. Rudkevich, D. M.; Verboom, W.; Reinhoudt, D. N. J. Org. Chem. 1994, 59, 3683-3686. Rudkevich, D. M.; Brzozka, Z.; Palys, M.; Visser, H. C.; Verboom, W.; Reinhoudt, D. N. Angew. Chem., Int. Ed. Engl. 1994, 33, 467-468. Savage, P. B.; Holmgren, S K.; Gellman, S. H. J. Am. Chem. Soc. 1994, 116, 4069-4070. Rudkevich, D. M.; Mercer-Chalmers, J. D.; Verboom, W.; Ungaro, R.; de Jong, F.; Reinhoudt, D. N. J. Am. Chem. Soc. 1995, 117, 6124-6125. Scheerder, J.; van Duynhoven, J. P. M.; Engbersen, J. F. J.; Reinhoudt, D. N. Angew. Chem., Int. Ed. Engl. 1996, 35, 1090- 1093. Pelizzi, N.; Casnati, A.; Friggeri, A.; Ungaro, R. J. Chem. Soc., Perkin Trans. 2 1998, 1307-1311.
41. For examples of other artificial ditopic receptors that bind ion pairs see: Reetz, M. T.; Niemeyer, C. M.; Harms, K. Angew. Chem., Int. Ed. Engl. 1991, 30, 1474-1476. Arafa, E. A.; Kinnear, K. I.; Lockhart, J. C. J. Chem. Soc., Chem. Commun. 1992, 61-64. Flack, S. S.; Chaumette, J. L.; Kilburn, J. D.; Langley, G. J.; Webster, M. J. Chem. Soc., Chem. Commun. 1993, 399-401. Rudkevich, D. M.; Verboom, W.; Reinhoudt, D. N. J. Org. Chem. 1994, 59, 3683-3686. Rudkevich, D. M.; Brzozka, Z.; Palys, M.; Visser, H. C.; Verboom, W.; Reinhoudt, D. N. Angew. Chem., Int. Ed. Engl. 1994, 33, 467-468. Savage, P. B.; Holmgren, S K.; Gellman, S. H. J. Am. Chem. Soc. 1994, 116, 4069-4070. Rudkevich, D. M.; Mercer-Chalmers, J. D.; Verboom, W.; Ungaro, R.; de Jong, F.; Reinhoudt, D. N. J. Am. Chem. Soc. 1995, 117, 6124-6125. Scheerder, J.; van Duynhoven, J. P. M.; Engbersen, J. F. J.; Reinhoudt, D. N. Angew. Chem., Int. Ed. Engl. 1996, 35, 1090-1093. Pelizzi, N.; Casnati, A.; Friggeri, A.; Ungaro, R. J. Chem. Soc., Perkin Trans. 2 1998, 1307-1311.
42. For examples of other artificial ditopic receptors that bind ion pairs see: Reetz, M. T.; Niemeyer, C. M.; Harms, K. Angew. Chem., Int. Ed. Engl. 1991, 30, 1474-1476. Arafa, E. A.; Kinnear, K. I.; Lockhart, J. C. J. Chem. Soc., Chem. Commun. 1992, 61-64. Flack, S. S.; Chaumette, J. L.; Kilburn, J. D.; Langley, G. J.; Webster, M. J. Chem. Soc., Chem. Commun. 1993, 399-401. Rudkevich, D. M.; Verboom, W.; Reinhoudt, D. N. J. Org. Chem. 1994, 59, 3683-3686. Rudkevich, D. M.; Brzozka, Z.; Palys, M.; Visser, H. C.; Verboom, W.; Reinhoudt, D. N. Angew. Chem., Int. Ed. Engl. 1994, 33, 467-468. Savage, P. B.; Holmgren, S K.; Gellman, S. H. J. Am. Chem. Soc. 1994, 116, 4069-4070. Rudkevich, D. M.; Mercer-Chalmers, J. D.; Verboom, W.; Ungaro, R.; de Jong, F.; Reinhoudt, D. N. J. Am. Chem. Soc. 1995, 117, 6124-6125. Scheerder, J.; van Duynhoven, J. P. M.; Engbersen, J. F. J.; Reinhoudt, D. N. Angew. Chem., Int. Ed. Engl. 1996, 35, 1090- 1093. Pelizzi, N.; Casnati, A.; Friggeri, A.; Ungaro, R. J. Chem. Soc., Perkin Trans. 2 1998, 1307-1311.
43. See for example: Richardson, J. S.; Richardson, D. C. In Prediction of protein structure and the principles of protein conformation; Fasman, G. D., Ed.; Plenum Press: New York, 1989; pp 1-98.
44. Gutsche, C. D. Calixarenes; RSC: London, 1989. Shinkai, S. Tetrahedron 1993, 49, 8933-8968. Böhmer, V. Angew. Chem., Int. Ed. Engl. 1995, 34, 713-745.
45. Gutsche, C. D. Calixarenes; RSC: London, 1989. Shinkai, S. Tetrahedron 1993, 49, 8933-8968. Böhmer, V. Angew. Chem., Int. Ed. Engl. 1995, 34, 713-745.
46. Gutsche, C. D. Calixarenes; RSC: London, 1989. Shinkai, S. Tetrahedron 1993, 49, 8933-8968. Böhmer, V. Angew. Chem., Int. Ed. Engl. 1995, 34, 713-745.
47. Deber, C. M.; Madison, V.; Blout, E. R. Acc. Chem. Res. 1976, 9, 106-113. Wüthrich, K. NMR in biological research: peptides and proteins; North-Holland Publ. Co.: Amsterdam, 1976.
48. Deber, C. M.; Madison, V.; Blout, E. R. Acc. Chem. Res. 1976, 9, 106-113. Wüthrich, K. NMR in biological research: peptides and proteins; North-Holland Publ. Co.: Amsterdam, 1976.
49. Néel, J. Pure Appl. Chem. 1872, 31, 201-225.
50. Vinogradov, S. N.; Ninnell, R. H. Hydrogen Bonding; Van Nostrand Reinhold Co.: New York, 1971.
51. Ma, J. C.; Dougherty, D. A. Chem. Rev. 1997, 97, 1303-1324.
52. Petti, M. A.; Shepodd, T. J.; Barrans, R. E., Jr.; Dougherty, D. A. J. Am. Chem. Soc. 1988, 110, 6825-6840. Stauffer, D. A.; Dougherty, D. A. Tetrahedron Lett. 1988, 29, 6039-6042. Kearney, P. C.; Mizoue, L. S.; Kumpf, R. A.; Forman, J. E.; McCurdy, A.; Dougherty, D. A. J. Am. Chem. Soc. 1993, 115, 9907-9919. Mecozzi, S.; West, A. P., Jr.; Dougherty, D. A. J. Am. Chem. Soc. 1996, 118, 2307-2308. Also other groups have described the complexation of cations by cyclophanes: Cattani, A.; Dalla Cort, A.; Mandolini, L. J. Org. Chem. 1995, 60, 8313-8314. Méric, R.; Lehn, J. M.; Vigneron, J. P. Bull. Soc. Chim. Fr. 1994, 131, 579-83.
53. Petti, M. A.; Shepodd, T. J.; Barrans, R. E., Jr.; Dougherty, D. A. J. Am. Chem. Soc. 1988, 110, 6825-6840. Stauffer, D. A.; Dougherty, D. A. Tetrahedron Lett. 1988, 29, 6039-6042. Kearney, P. C.; Mizoue, L. S.; Kumpf, R. A.; Forman, J. E.; McCurdy, A.; Dougherty, D. A. J. Am. Chem. Soc. 1993, 115, 9907-9919. Mecozzi, S.; West, A. P., Jr.; Dougherty, D. A. J. Am. Chem. Soc. 1996, 118, 2307-2308. Also other groups have described the complexation of cations by cyclophanes: Cattani, A.; Dalla Cort, A.; Mandolini, L. J. Org. Chem. 1995, 60, 8313-8314. Méric, R.; Lehn, J. M.; Vigneron, J. P. Bull. Soc. Chim. Fr. 1994, 131, 579-83.
54. Petti, M. A.; Shepodd, T. J.; Barrans, R. E., Jr.; Dougherty, D. A. J. Am. Chem. Soc. 1988, 110, 6825-6840. Stauffer, D. A.; Dougherty, D. A. Tetrahedron Lett. 1988, 29, 6039-6042. Kearney, P. C.; Mizoue, L. S.; Kumpf, R. A.; Forman, J. E.; McCurdy, A.; Dougherty, D. A. J. Am. Chem. Soc. 1993, 115, 9907-9919. Mecozzi, S.; West, A. P., Jr.; Dougherty, D. A. J. Am. Chem. Soc. 1996, 118, 2307-2308. Also other groups have described the complexation of cations by cyclophanes: Cattani, A.; Dalla Cort, A.; Mandolini, L. J. Org. Chem. 1995, 60, 8313-8314. Méric, R.; Lehn, J. M.; Vigneron, J. P. Bull. Soc. Chim. Fr. 1994, 131, 579-83.
55. Petti, M. A.; Shepodd, T. J.; Barrans, R. E., Jr.; Dougherty, D. A. J. Am. Chem. Soc. 1988, 110, 6825-6840. Stauffer, D. A.; Dougherty, D. A. Tetrahedron Lett. 1988, 29, 6039-6042. Kearney, P. C.; Mizoue, L. S.; Kumpf, R. A.; Forman, J. E.; McCurdy, A.; Dougherty, D. A. J. Am. Chem. Soc. 1993, 115, 9907-9919. Mecozzi, S.; West, A. P., Jr.; Dougherty, D. A. J. Am. Chem. Soc. 1996, 118, 2307-2308. Also other groups have described the complexation of cations by cyclophanes: Cattani, A.; Dalla Cort, A.; Mandolini, L. J. Org. Chem. 1995, 60, 8313-8314. Méric, R.; Lehn, J. M.; Vigneron, J. P. Bull. Soc. Chim. Fr. 1994, 131, 579-83.
56. Petti, M. A.; Shepodd, T. J.; Barrans, R. E., Jr.; Dougherty, D. A. J. Am. Chem. Soc. 1988, 110, 6825-6840. Stauffer, D. A.; Dougherty, D. A. Tetrahedron Lett. 1988, 29, 6039-6042. Kearney, P. C.; Mizoue, L. S.; Kumpf, R. A.; Forman, J. E.; McCurdy, A.; Dougherty, D. A. J. Am. Chem. Soc. 1993, 115, 9907-9919. Mecozzi, S.; West, A. P., Jr.; Dougherty, D. A. J. Am. Chem. Soc. 1996, 118, 2307-2308. Also other groups have described the complexation of cations by cyclophanes: Cattani, A.; Dalla Cort, A.; Mandolini, L. J. Org. Chem. 1995, 60, 8313-8314. Méric, R.; Lehn, J. M.; Vigneron, J. P. Bull. Soc. Chim. Fr. 1994, 131, 579-83.
57. Petti, M. A.; Shepodd, T. J.; Barrans, R. E., Jr.; Dougherty, D. A. J. Am. Chem. Soc. 1988, 110, 6825-6840. Stauffer, D. A.; Dougherty, D. A. Tetrahedron Lett. 1988, 29, 6039-6042. Kearney, P. C.; Mizoue, L. S.; Kumpf, R. A.; Forman, J. E.; McCurdy, A.; Dougherty, D. A. J. Am. Chem. Soc. 1993, 115, 9907-9919. Mecozzi, S.; West, A. P., Jr.; Dougherty, D. A. J. Am. Chem. Soc. 1996, 118, 2307-2308. Also other groups have described the complexation of cations by cyclophanes: Cattani, A.; Dalla Cort, A.; Mandolini, L. J. Org. Chem. 1995, 60, 8313-8314. Méric, R.; Lehn, J. M.; Vigneron, J. P. Bull. Soc. Chim. Fr. 1994, 131, 579-83.
58. (a) De Iasi, G.; Masci, B. Tetrahedron Lett. 1993, 34, 6635-6638.
59. (b) Masci, B. Tetrahedron 1995, 57, 5459-5464.
60. (c) Masci, B.; Finelli, M.; Varrone, M. Chem. Eur. J. 1998, 4, 2018-2030.
61. Garel, L.; Lozach, B.; Dutasta, J.-P.; Collet, A. J. Am. Chem. Soc. 1993, 115, 11652-11653.
62. Dougherty, D. A.; Stauffer, D. A. Science 1990, 250, 1558-1560. Dougherty, D. A. Science 1996, 271, 163-168.
63. Dougherty, D. A.; Stauffer, D. A. Science 1990, 250, 1558-1560. Dougherty, D. A. Science 1996, 271, 163-168.
64. Roelens, S.; Torriti, R. J. Am. Chem. Soc. 1998, 120, 12443-12452.
65. Connors, K. A. Binding Constants; Wiley: New York, 1987. Macomber, R. S. J. Chem. Educ. 1992, 69, 375-378.
66. Connors, K. A. Binding Constants; Wiley: New York, 1987. Macomber, R. S. J. Chem. Educ. 1992, 69, 375-378.
67. Reetz, M. T.; Hütte, S.; Goddard, R. J. Am. Chem. Soc. 1993, 115, 9339-9340.
68. Jeffreys, J. A. D.; Ferguson, G. J. Chem. Soc. B 1970, 826-829.
69. Funato, N.; Takayanagi, H.; Konda, Y.; Toda, Y.; Harigaya, Y.; Iwai, Y.; Omura, S. Tetrahedron Lett. 1994, 35, 1251-1254.
70. Nishida, H.; Takada, N.; Yoshimura, M.; Sonoda, T.; Kobayashi, H. Bull. Chem. Soc. Jpn. 1984, 57, 2600-2604. Bell, D. A.; Anslyn, E. V. Tetrahedron 1995, 51, 7161-7172.
71. Nishida, H.; Takada, N.; Yoshimura, M.; Sonoda, T.; Kobayashi, H. Bull. Chem. Soc. Jpn. 1984, 57, 2600-2604. Bell, D. A.; Anslyn, E. V. Tetrahedron 1995, 51, 7161-7172.
72. Doxsee, K. M. J. Org. Chem. 1989, 54, 4712-4715. Olsher, U.; Hankins, M. G.; Kim, Y. D.; Bartsch, R. A. J. Am. Chem. Soc. 1993, 115, 3370-3371. In these papers it was speculated that the influence of anions on the affinity of certain crown ethers toward cations may be attributed to specific effects of the anions on the conformation of the host in the final complex. In this respect, these publications are related to this work.
73. Doxsee, K. M. J. Org. Chem. 1989, 54, 4712-4715. Olsher, U.; Hankins, M. G.; Kim, Y. D.; Bartsch, R. A. J. Am. Chem. Soc. 1993, 115, 3370-3371. In these papers it was speculated that the influence of anions on the affinity of certain crown ethers toward cations may be attributed to specific effects of the anions on the conformation of the host in the final complex. In this respect, these publications are related to this work.
74. Coste, J.; Frérot, E.; Jouin, P. J. Org. Chem. 1994, 59, 2437-2446.
75. The crystallographic data (without structure factors) for 2 and 2·N-methylquinuclidinium iodide have been deposited as supplementary publications CCDC-126020 and CCDC-126021 at the Cambridge Crystallographic Data Centre. Copies of the data can be obtained from the following: The Director, CCDC, 12 Union Road, Cambridge CB2 1EZ, U.K. (Telefax +44-1223/336-033. E-mail: deposit@ccdc.cam.ac.uk.)
76. Sheldrick, G. M. Acta Crystallogr., Sect. A 1990, A46, 467-473.
77. Sheldrick, G. M. SHELXL-97, Program for Crystal Structure Refinement, Universität Göttingen, 1997.