Highly stable self-assembly in water: Ion pair driven dimerization of a guanidiniocarbonyl pyrrole carboxylate zwitterion

Journal of the American Chemical Society

Volumn 125, Issue 2, 2003, Pages 452-459

  Schmuck, Carsten ^a   Wienand, Wolfgang ^a  

^a UNIVERSITY OF WÜRZBURG   (Germany)

Author keywords

[No Author keywords available]

Indexed keywords

ELECTROSTATIC INTERACTION; HYDROGEN BONDING NETWORK;

CARBOXYLIC ACIDS; DIMERIZATION; NUCLEAR MAGNETIC RESONANCE; ORGANIC SOLVENTS; SOLUTIONS;

SYNTHESIS (CHEMICAL);

AMPHOLYTE; CARBOXYLIC ACID DERIVATIVE; PYRROLE DERIVATIVE; WATER;

AQUEOUS SOLUTION; ARTICLE; COMPARATIVE STUDY; DIMERIZATION; ELECTRICITY; HYDROGEN BOND; MOLECULAR STABILITY; NUCLEAR MAGNETIC RESONANCE; SYNTHESIS; X RAY ANALYSIS;

EID: 0037438509     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja028485+     Document Type: Article

References (104)

1. For general references on supramolecular chemistry, see: (a) Schneider, H. J.; Yatsimirsky, A. Principles and Methods in Supramolecular Chemistry: Wiley-VCH: Weinheim, 2000. (b) Steed, J. W.; Atwood, J. L. Supramolecular Chemistry; Wiley: Chichester, 2000. (c) Lehn, J.-M. Supramolecular Chemistry; Concepts and Perspectives; VCH: Weinheim, 1995. (d) Vögtle, F. Supramolecular Chemistry; J. Wiley & Sons: Chichester, 1991.
2. For general references on supramolecular chemistry, see: (a) Schneider, H. J.; Yatsimirsky, A. Principles and Methods in Supramolecular Chemistry: Wiley-VCH: Weinheim, 2000. (b) Steed, J. W.; Atwood, J. L. Supramolecular Chemistry; Wiley: Chichester, 2000. (c) Lehn, J.-M. Supramolecular Chemistry; Concepts and Perspectives; VCH: Weinheim, 1995. (d) Vögtle, F. Supramolecular Chemistry; J. Wiley & Sons: Chichester, 1991.
3. For general references on supramolecular chemistry, see: (a) Schneider, H. J.; Yatsimirsky, A. Principles and Methods in Supramolecular Chemistry: Wiley-VCH: Weinheim, 2000. (b) Steed, J. W.; Atwood, J. L. Supramolecular Chemistry; Wiley: Chichester, 2000. (c) Lehn, J.-M. Supramolecular Chemistry; Concepts and Perspectives; VCH: Weinheim, 1995. (d) Vögtle, F. Supramolecular Chemistry; J. Wiley & Sons: Chichester, 1991.
4. For general references on supramolecular chemistry, see: (a) Schneider, H. J.; Yatsimirsky, A. Principles and Methods in Supramolecular Chemistry: Wiley-VCH: Weinheim, 2000. (b) Steed, J. W.; Atwood, J. L. Supramolecular Chemistry; Wiley: Chichester, 2000. (c) Lehn, J.-M. Supramolecular Chemistry; Concepts and Perspectives; VCH: Weinheim, 1995. (d) Vögtle, F. Supramolecular Chemistry; J. Wiley & Sons: Chichester, 1991.
5. (a) Reinhoudt, D. N.; Crego-Calama, M. Science 2002, 295, 2403-2407.
6. (b) Menger, F. M. Proc. Natl. Acad. Sci. U.S.A. 2002. 99, 4818-4822.
7. (c) Stoddart, F. J.; Tseng, H.-R. Proc. Natl. Acad. Sci. U.S.A. 2002, 99, 4797-4800.
8. (d) Lehn, J.-M. Proc. Natl. Acad. Sci. U.S.A. 2002, 99, 4763-4768.
9. (e) Whitesides, G. M.; Simanek, E. E.; Mathias, J. P.; Seto, C. T.; Chin, D.; Mammen, M.; Gordon, D. M. Acc. Chem. Res. 1995, 28, 37-44.
10. (a) Whitesides, G. M.; Mathias, J. P.; Seto, C. T. Science 1991, 254, 1312-1319.
11. (b) Bowden, N. B.; Weck, M. M.; Choi, I. S.; Whitesides, G. M. Acc. Chem. Res. 2001, 34, 231-238.
12. (c) Sharma, C. V. K. J. Chem. Educ. 2001, 78, 617-622.
13. (d) Rouvray, D. Chem. Brit. 2000, 26-29.
14. (e) Lawrence, D. S.; Jiang, T.; Levett, M. Chem. Rev. 1995, 95, 2229-2260.
15. (a) Whitesides, G. M.; Boncheva, M. Proc. Natl. Acad. Sci. U.S.A. 2002, 99, 4769-4774.
16. (b) Philp, D.; Stoddart, J. F. Angew. Chem., Int. Ed. Engl. 1996, 35, 1155-1196.
17. (c) Lawrence, D. S.; Jiang, T.; Levitt, M. Chem. Rev. 1995, 95, 2229-2260.
18. This is especially obvious in the case of supramolecular polymers: (a) Schmuck, C.; Wienand, W. Angew. Chem., Int. Ed. 2001, 40, 4363-4369. (b) Sherrington, D. C.; Taskinen, K. A. Chem. Soc. Rev. 2001, 30. 83-93.
19. This is especially obvious in the case of supramolecular polymers: (a) Schmuck, C.; Wienand, W. Angew. Chem., Int. Ed. 2001, 40, 4363-4369. (b) Sherrington, D. C.; Taskinen, K. A. Chem. Soc. Rev. 2001, 30. 83-93.
20. For work on self-assembly in the solid-state, see for example: (a) Bishop, R. Synlett 1999, 1351-1359. (b) Weber, E., Ed. Design of Organic Solids, Top. Curr. Chem. 1998, 198. (c) Desiraju, G. R. Angew. Chem., Int. Ed. Engl. 1995, 34, 2328-2345. (d) Desiraju, G. R. Crystal Engineering: The Design of Organic Solids; Elsevier: New York, 1989. (e) Wright, J. D. Molecular Crystals; Cambridge University Press: Cambridge, 1987. (f) Chin, D. N.; Palmore, T. R.; Whitesides, G. M. J. Am. Chem. Soc. 1999, 121, 2115-2132.
21. For work on self-assembly in the solid-state, see for example: (a) Bishop, R. Synlett 1999, 1351-1359. (b) Weber, E., Ed. Design of Organic Solids, Top. Curr. Chem. 1998, 198. (c) Desiraju, G. R. Angew. Chem., Int. Ed. Engl. 1995, 34, 2328-2345. (d) Desiraju, G. R. Crystal Engineering: The Design of Organic Solids; Elsevier: New York, 1989. (e) Wright, J. D. Molecular Crystals; Cambridge University Press: Cambridge, 1987. (f) Chin, D. N.; Palmore, T. R.; Whitesides, G. M. J. Am. Chem. Soc. 1999, 121, 2115-2132.
22. For work on self-assembly in the solid-state, see for example: (a) Bishop, R. Synlett 1999, 1351-1359. (b) Weber, E., Ed. Design of Organic Solids, Top. Curr. Chem. 1998, 198. (c) Desiraju, G. R. Angew. Chem., Int. Ed. Engl. 1995, 34, 2328-2345. (d) Desiraju, G. R. Crystal Engineering: The Design of Organic Solids; Elsevier: New York, 1989. (e) Wright, J. D. Molecular Crystals; Cambridge University Press: Cambridge, 1987. (f) Chin, D. N.; Palmore, T. R.; Whitesides, G. M. J. Am. Chem. Soc. 1999, 121, 2115-2132.
23. For work on self-assembly in the solid-state, see for example: (a) Bishop, R. Synlett 1999, 1351-1359. (b) Weber, E., Ed. Design of Organic Solids, Top. Curr. Chem. 1998, 198. (c) Desiraju, G. R. Angew. Chem., Int. Ed. Engl. 1995, 34, 2328-2345. (d) Desiraju, G. R. Crystal Engineering: The Design of Organic Solids; Elsevier: New York, 1989. (e) Wright, J. D. Molecular Crystals; Cambridge University Press: Cambridge, 1987. (f) Chin, D. N.; Palmore, T. R.; Whitesides, G. M. J. Am. Chem. Soc. 1999, 121, 2115-2132.
24. For work on self-assembly in the solid-state, see for example: (a) Bishop, R. Synlett 1999, 1351-1359. (b) Weber, E., Ed. Design of Organic Solids, Top. Curr. Chem. 1998, 198. (c) Desiraju, G. R. Angew. Chem., Int. Ed. Engl. 1995, 34, 2328-2345. (d) Desiraju, G. R. Crystal Engineering: The Design of Organic Solids; Elsevier: New York, 1989. (e) Wright, J. D. Molecular Crystals; Cambridge University Press: Cambridge, 1987. (f) Chin, D. N.; Palmore, T. R.; Whitesides, G. M. J. Am. Chem. Soc. 1999, 121, 2115-2132.
25. For work on self-assembly in the solid-state, see for example: (a) Bishop, R. Synlett 1999, 1351-1359. (b) Weber, E., Ed. Design of Organic Solids, Top. Curr. Chem. 1998, 198. (c) Desiraju, G. R. Angew. Chem., Int. Ed. Engl. 1995, 34, 2328-2345. (d) Desiraju, G. R. Crystal Engineering: The Design of Organic Solids; Elsevier: New York, 1989. (e) Wright, J. D. Molecular Crystals; Cambridge University Press: Cambridge, 1987. (f) Chin, D. N.; Palmore, T. R.; Whitesides, G. M. J. Am. Chem. Soc. 1999, 121, 2115-2132.
26. For review articles on hydrogen-bonded self-assembly in organic solvents, see for example: (a) Zimmermann, S. C.; Corbin, P. S. Struct. Bonding 2000, 63-94. (b) Schalley, C. A.; Rebek, J., Jr. Chemical Encapsulation in Self-Assembling Capsules. In Stimulating Concepts in Chemistry; Vögtle, F., Stoddart, J. F., Shibasaki, M., Eds.; Wiley-VCH: Weinheim, 2000: pp 199-210. (c) Rebek, J., Jr. Acc. Chem. Res. 1999, 32, 278-286. (d) Conn, M. M.; Rebek, J., Jr. Chem. Rev. 1997, 97, 1647-1668. (e) 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. (f) MacDonald, C.; Whitesides, G. M. Chem. Rev. 1994, 94, 2383-2420.
27. For review articles on hydrogen-bonded self-assembly in organic solvents, see for example: (a) Zimmermann, S. C.; Corbin, P. S. Struct. Bonding 2000, 63-94. (b) Schalley, C. A.; Rebek, J., Jr. Chemical Encapsulation in Self-Assembling Capsules. In Stimulating Concepts in Chemistry; Vögtle, F., Stoddart, J. F., Shibasaki, M., Eds.; Wiley-VCH: Weinheim, 2000: pp 199-210. (c) Rebek, J., Jr. Acc. Chem. Res. 1999, 32, 278-286. (d) Conn, M. M.; Rebek, J., Jr. Chem. Rev. 1997, 97, 1647-1668. (e) 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. (f) MacDonald, C.; Whitesides, G. M. Chem. Rev. 1994, 94, 2383-2420.
28. For review articles on hydrogen-bonded self-assembly in organic solvents, see for example: (a) Zimmermann, S. C.; Corbin, P. S. Struct. Bonding 2000, 63-94. (b) Schalley, C. A.; Rebek, J., Jr. Chemical Encapsulation in Self-Assembling Capsules. In Stimulating Concepts in Chemistry; Vögtle, F., Stoddart, J. F., Shibasaki, M., Eds.; Wiley-VCH: Weinheim, 2000: pp 199-210. (c) Rebek, J., Jr. Acc. Chem. Res. 1999, 32, 278-286. (d) Conn, M. M.; Rebek, J., Jr. Chem. Rev. 1997, 97, 1647-1668. (e) 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. (f) MacDonald, C.; Whitesides, G. M. Chem. Rev. 1994, 94, 2383-2420.
29. For review articles on hydrogen-bonded self-assembly in organic solvents, see for example: (a) Zimmermann, S. C.; Corbin, P. S. Struct. Bonding 2000, 63-94. (b) Schalley, C. A.; Rebek, J., Jr. Chemical Encapsulation in Self-Assembling Capsules. In Stimulating Concepts in Chemistry; Vögtle, F., Stoddart, J. F., Shibasaki, M., Eds.; Wiley-VCH: Weinheim, 2000: pp 199-210. (c) Rebek, J., Jr. Acc. Chem. Res. 1999, 32, 278-286. (d) Conn, M. M.; Rebek, J., Jr. Chem. Rev. 1997, 97, 1647-1668. (e) 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. (f) MacDonald, C.; Whitesides, G. M. Chem. Rev. 1994, 94, 2383-2420.
30. For review articles on hydrogen-bonded self-assembly in organic solvents, see for example: (a) Zimmermann, S. C.; Corbin, P. S. Struct. Bonding 2000, 63-94. (b) Schalley, C. A.; Rebek, J., Jr. Chemical Encapsulation in Self-Assembling Capsules. In Stimulating Concepts in Chemistry; Vögtle, F., Stoddart, J. F., Shibasaki, M., Eds.; Wiley-VCH: Weinheim, 2000: pp 199-210. (c) Rebek, J., Jr. Acc. Chem. Res. 1999, 32, 278-286. (d) Conn, M. M.; Rebek, J., Jr. Chem. Rev. 1997, 97, 1647-1668. (e) 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. (f) MacDonald, C.; Whitesides, G. M. Chem. Rev. 1994, 94, 2383-2420.
31. For review articles on hydrogen-bonded self-assembly in organic solvents, see for example: (a) Zimmermann, S. C.; Corbin, P. S. Struct. Bonding 2000, 63-94. (b) Schalley, C. A.; Rebek, J., Jr. Chemical Encapsulation in Self-Assembling Capsules. In Stimulating Concepts in Chemistry; Vögtle, F., Stoddart, J. F., Shibasaki, M., Eds.; Wiley-VCH: Weinheim, 2000: pp 199-210. (c) Rebek, J., Jr. Acc. Chem. Res. 1999, 32, 278-286. (d) Conn, M. M.; Rebek, J., Jr. Chem. Rev. 1997, 97, 1647-1668. (e) 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. (f) MacDonald, C.; Whitesides, G. M. Chem. Rev. 1994, 94, 2383-2420.
32. Some recent examples can be found in: (a) Conn, M. M.; Rebek, J. Chem. Rev. 1997, 97, 1647-1668. (b) Kikuchi, Y.; Tanaka, Y.; Sutarto, S.; Kobayashi, K.; Toi, H.; Aoyama, Y. J. Am. Chem. Soc. 1992, 114, 10302-10306. (c) Mammen, M.; Simanek, E. E.; Whitesides, G. M. J. Am. Chem. Soc. 1996, 118, 12614-12623. (d) Vreekamp, R. H.; Verboom, W.; Reinhoudt, D. N. J. Org. Chem. 1996, 61, 4282-4288. (e) Mogck, O.; Böhmer, V.; Vogt, W. Tetrahedron 1996, 52, 8489-8496. (f) Sessler, J. L.; Wang, R. J. Am. Chem. Soc. 1996, 118, 9808-9809. (g) Heinz, T.; Rudkevich, D. M.; Rebek, J. Nature 1998, 394, 764-767. (h) Martín, T.; Obst, U.; Rebek, J. Science 1998, 281, 1842-1845. (i) Prins, L. J.; Huskens, J.; de Jong, F.; Timmerman, P.; Reinhoudt, D. N. Nature 1999, 398, 498-502. (j) Hof, F.; Nuckolls, C.; Craig, S. L.; Martín, T.; Rebek, J. J. Am. Chem. Soc. 2000, 122, 10991-10996. (k) Rivera, J. M.; Craig, S. L.; Martín, T.; Rebek, J. Angew. Chem., Int. Ed. 2000, 39, 2130-2132.
33. Some recent examples can be found in: (a) Conn, M. M.; Rebek, J. Chem. Rev. 1997, 97, 1647-1668. (b) Kikuchi, Y.; Tanaka, Y.; Sutarto, S.; Kobayashi, K.; Toi, H.; Aoyama, Y. J. Am. Chem. Soc. 1992, 114, 10302-10306. (c) Mammen, M.; Simanek, E. E.; Whitesides, G. M. J. Am. Chem. Soc. 1996, 118, 12614-12623. (d) Vreekamp, R. H.; Verboom, W.; Reinhoudt, D. N. J. Org. Chem. 1996, 61, 4282-4288. (e) Mogck, O.; Böhmer, V.; Vogt, W. Tetrahedron 1996, 52, 8489-8496. (f) Sessler, J. L.; Wang, R. J. Am. Chem. Soc. 1996, 118, 9808-9809. (g) Heinz, T.; Rudkevich, D. M.; Rebek, J. Nature 1998, 394, 764-767. (h) Martín, T.; Obst, U.; Rebek, J. Science 1998, 281, 1842-1845. (i) Prins, L. J.; Huskens, J.; de Jong, F.; Timmerman, P.; Reinhoudt, D. N. Nature 1999, 398, 498-502. (j) Hof, F.; Nuckolls, C.; Craig, S. L.; Martín, T.; Rebek, J. J. Am. Chem. Soc. 2000, 122, 10991-10996. (k) Rivera, J. M.; Craig, S. L.; Martín, T.; Rebek, J. Angew. Chem., Int. Ed. 2000, 39, 2130-2132.
34. Some recent examples can be found in: (a) Conn, M. M.; Rebek, J. Chem. Rev. 1997, 97, 1647-1668. (b) Kikuchi, Y.; Tanaka, Y.; Sutarto, S.; Kobayashi, K.; Toi, H.; Aoyama, Y. J. Am. Chem. Soc. 1992, 114, 10302-10306. (c) Mammen, M.; Simanek, E. E.; Whitesides, G. M. J. Am. Chem. Soc. 1996, 118, 12614-12623. (d) Vreekamp, R. H.; Verboom, W.; Reinhoudt, D. N. J. Org. Chem. 1996, 61, 4282-4288. (e) Mogck, O.; Böhmer, V.; Vogt, W. Tetrahedron 1996, 52, 8489-8496. (f) Sessler, J. L.; Wang, R. J. Am. Chem. Soc. 1996, 118, 9808-9809. (g) Heinz, T.; Rudkevich, D. M.; Rebek, J. Nature 1998, 394, 764-767. (h) Martín, T.; Obst, U.; Rebek, J. Science 1998, 281, 1842-1845. (i) Prins, L. J.; Huskens, J.; de Jong, F.; Timmerman, P.; Reinhoudt, D. N. Nature 1999, 398, 498-502. (j) Hof, F.; Nuckolls, C.; Craig, S. L.; Martín, T.; Rebek, J. J. Am. Chem. Soc. 2000, 122, 10991-10996. (k) Rivera, J. M.; Craig, S. L.; Martín, T.; Rebek, J. Angew. Chem., Int. Ed. 2000, 39, 2130-2132.
35. Some recent examples can be found in: (a) Conn, M. M.; Rebek, J. Chem. Rev. 1997, 97, 1647-1668. (b) Kikuchi, Y.; Tanaka, Y.; Sutarto, S.; Kobayashi, K.; Toi, H.; Aoyama, Y. J. Am. Chem. Soc. 1992, 114, 10302-10306. (c) Mammen, M.; Simanek, E. E.; Whitesides, G. M. J. Am. Chem. Soc. 1996, 118, 12614-12623. (d) Vreekamp, R. H.; Verboom, W.; Reinhoudt, D. N. J. Org. Chem. 1996, 61, 4282-4288. (e) Mogck, O.; Böhmer, V.; Vogt, W. Tetrahedron 1996, 52, 8489-8496. (f) Sessler, J. L.; Wang, R. J. Am. Chem. Soc. 1996, 118, 9808-9809. (g) Heinz, T.; Rudkevich, D. M.; Rebek, J. Nature 1998, 394, 764-767. (h) Martín, T.; Obst, U.; Rebek, J. Science 1998, 281, 1842-1845. (i) Prins, L. J.; Huskens, J.; de Jong, F.; Timmerman, P.; Reinhoudt, D. N. Nature 1999, 398, 498-502. (j) Hof, F.; Nuckolls, C.; Craig, S. L.; Martín, T.; Rebek, J. J. Am. Chem. Soc. 2000, 122, 10991-10996. (k) Rivera, J. M.; Craig, S. L.; Martín, T.; Rebek, J. Angew. Chem., Int. Ed. 2000, 39, 2130-2132.
36. Some recent examples can be found in: (a) Conn, M. M.; Rebek, J. Chem. Rev. 1997, 97, 1647-1668. (b) Kikuchi, Y.; Tanaka, Y.; Sutarto, S.; Kobayashi, K.; Toi, H.; Aoyama, Y. J. Am. Chem. Soc. 1992, 114, 10302-10306. (c) Mammen, M.; Simanek, E. E.; Whitesides, G. M. J. Am. Chem. Soc. 1996, 118, 12614-12623. (d) Vreekamp, R. H.; Verboom, W.; Reinhoudt, D. N. J. Org. Chem. 1996, 61, 4282-4288. (e) Mogck, O.; Böhmer, V.; Vogt, W. Tetrahedron 1996, 52, 8489-8496. (f) Sessler, J. L.; Wang, R. J. Am. Chem. Soc. 1996, 118, 9808-9809. (g) Heinz, T.; Rudkevich, D. M.; Rebek, J. Nature 1998, 394, 764-767. (h) Martín, T.; Obst, U.; Rebek, J. Science 1998, 281, 1842-1845. (i) Prins, L. J.; Huskens, J.; de Jong, F.; Timmerman, P.; Reinhoudt, D. N. Nature 1999, 398, 498-502. (j) Hof, F.; Nuckolls, C.; Craig, S. L.; Martín, T.; Rebek, J. J. Am. Chem. Soc. 2000, 122, 10991-10996. (k) Rivera, J. M.; Craig, S. L.; Martín, T.; Rebek, J. Angew. Chem., Int. Ed. 2000, 39, 2130-2132.
37. Some recent examples can be found in: (a) Conn, M. M.; Rebek, J. Chem. Rev. 1997, 97, 1647-1668. (b) Kikuchi, Y.; Tanaka, Y.; Sutarto, S.; Kobayashi, K.; Toi, H.; Aoyama, Y. J. Am. Chem. Soc. 1992, 114, 10302-10306. (c) Mammen, M.; Simanek, E. E.; Whitesides, G. M. J. Am. Chem. Soc. 1996, 118, 12614-12623. (d) Vreekamp, R. H.; Verboom, W.; Reinhoudt, D. N. J. Org. Chem. 1996, 61, 4282-4288. (e) Mogck, O.; Böhmer, V.; Vogt, W. Tetrahedron 1996, 52, 8489-8496. (f) Sessler, J. L.; Wang, R. J. Am. Chem. Soc. 1996, 118, 9808-9809. (g) Heinz, T.; Rudkevich, D. M.; Rebek, J. Nature 1998, 394, 764-767. (h) Martín, T.; Obst, U.; Rebek, J. Science 1998, 281, 1842-1845. (i) Prins, L. J.; Huskens, J.; de Jong, F.; Timmerman, P.; Reinhoudt, D. N. Nature 1999, 398, 498-502. (j) Hof, F.; Nuckolls, C.; Craig, S. L.; Martín, T.; Rebek, J. J. Am. Chem. Soc. 2000, 122, 10991-10996. (k) Rivera, J. M.; Craig, S. L.; Martín, T.; Rebek, J. Angew. Chem., Int. Ed. 2000, 39, 2130-2132.
38. Some recent examples can be found in: (a) Conn, M. M.; Rebek, J. Chem. Rev. 1997, 97, 1647-1668. (b) Kikuchi, Y.; Tanaka, Y.; Sutarto, S.; Kobayashi, K.; Toi, H.; Aoyama, Y. J. Am. Chem. Soc. 1992, 114, 10302-10306. (c) Mammen, M.; Simanek, E. E.; Whitesides, G. M. J. Am. Chem. Soc. 1996, 118, 12614-12623. (d) Vreekamp, R. H.; Verboom, W.; Reinhoudt, D. N. J. Org. Chem. 1996, 61, 4282-4288. (e) Mogck, O.; Böhmer, V.; Vogt, W. Tetrahedron 1996, 52, 8489-8496. (f) Sessler, J. L.; Wang, R. J. Am. Chem. Soc. 1996, 118, 9808-9809. (g) Heinz, T.; Rudkevich, D. M.; Rebek, J. Nature 1998, 394, 764-767. (h) Martín, T.; Obst, U.; Rebek, J. Science 1998, 281, 1842-1845. (i) Prins, L. J.; Huskens, J.; de Jong, F.; Timmerman, P.; Reinhoudt, D. N. Nature 1999, 398, 498-502. (j) Hof, F.; Nuckolls, C.; Craig, S. L.; Martín, T.; Rebek, J. J. Am. Chem. Soc. 2000, 122, 10991-10996. (k) Rivera, J. M.; Craig, S. L.; Martín, T.; Rebek, J. Angew. Chem., Int. Ed. 2000, 39, 2130-2132.
39. Some recent examples can be found in: (a) Conn, M. M.; Rebek, J. Chem. Rev. 1997, 97, 1647-1668. (b) Kikuchi, Y.; Tanaka, Y.; Sutarto, S.; Kobayashi, K.; Toi, H.; Aoyama, Y. J. Am. Chem. Soc. 1992, 114, 10302-10306. (c) Mammen, M.; Simanek, E. E.; Whitesides, G. M. J. Am. Chem. Soc. 1996, 118, 12614-12623. (d) Vreekamp, R. H.; Verboom, W.; Reinhoudt, D. N. J. Org. Chem. 1996, 61, 4282-4288. (e) Mogck, O.; Böhmer, V.; Vogt, W. Tetrahedron 1996, 52, 8489-8496. (f) Sessler, J. L.; Wang, R. J. Am. Chem. Soc. 1996, 118, 9808-9809. (g) Heinz, T.; Rudkevich, D. M.; Rebek, J. Nature 1998, 394, 764-767. (h) Martín, T.; Obst, U.; Rebek, J. Science 1998, 281, 1842-1845. (i) Prins, L. J.; Huskens, J.; de Jong, F.; Timmerman, P.; Reinhoudt, D. N. Nature 1999, 398, 498-502. (j) Hof, F.; Nuckolls, C.; Craig, S. L.; Martín, T.; Rebek, J. J. Am. Chem. Soc. 2000, 122, 10991-10996. (k) Rivera, J. M.; Craig, S. L.; Martín, T.; Rebek, J. Angew. Chem., Int. Ed. 2000, 39, 2130-2132.
40. Some recent examples can be found in: (a) Conn, M. M.; Rebek, J. Chem. Rev. 1997, 97, 1647-1668. (b) Kikuchi, Y.; Tanaka, Y.; Sutarto, S.; Kobayashi, K.; Toi, H.; Aoyama, Y. J. Am. Chem. Soc. 1992, 114, 10302-10306. (c) Mammen, M.; Simanek, E. E.; Whitesides, G. M. J. Am. Chem. Soc. 1996, 118, 12614-12623. (d) Vreekamp, R. H.; Verboom, W.; Reinhoudt, D. N. J. Org. Chem. 1996, 61, 4282-4288. (e) Mogck, O.; Böhmer, V.; Vogt, W. Tetrahedron 1996, 52, 8489-8496. (f) Sessler, J. L.; Wang, R. J. Am. Chem. Soc. 1996, 118, 9808-9809. (g) Heinz, T.; Rudkevich, D. M.; Rebek, J. Nature 1998, 394, 764-767. (h) Martín, T.; Obst, U.; Rebek, J. Science 1998, 281, 1842-1845. (i) Prins, L. J.; Huskens, J.; de Jong, F.; Timmerman, P.; Reinhoudt, D. N. Nature 1999, 398, 498-502. (j) Hof, F.; Nuckolls, C.; Craig, S. L.; Martín, T.; Rebek, J. J. Am. Chem. Soc. 2000, 122, 10991-10996. (k) Rivera, J. M.; Craig, S. L.; Martín, T.; Rebek, J. Angew. Chem., Int. Ed. 2000, 39, 2130-2132.
41. Some recent examples can be found in: (a) Conn, M. M.; Rebek, J. Chem. Rev. 1997, 97, 1647-1668. (b) Kikuchi, Y.; Tanaka, Y.; Sutarto, S.; Kobayashi, K.; Toi, H.; Aoyama, Y. J. Am. Chem. Soc. 1992, 114, 10302-10306. (c) Mammen, M.; Simanek, E. E.; Whitesides, G. M. J. Am. Chem. Soc. 1996, 118, 12614-12623. (d) Vreekamp, R. H.; Verboom, W.; Reinhoudt, D. N. J. Org. Chem. 1996, 61, 4282-4288. (e) Mogck, O.; Böhmer, V.; Vogt, W. Tetrahedron 1996, 52, 8489-8496. (f) Sessler, J. L.; Wang, R. J. Am. Chem. Soc. 1996, 118, 9808-9809. (g) Heinz, T.; Rudkevich, D. M.; Rebek, J. Nature 1998, 394, 764-767. (h) Martín, T.; Obst, U.; Rebek, J. Science 1998, 281, 1842-1845. (i) Prins, L. J.; Huskens, J.; de Jong, F.; Timmerman, P.; Reinhoudt, D. N. Nature 1999, 398, 498-502. (j) Hof, F.; Nuckolls, C.; Craig, S. L.; Martín, T.; Rebek, J. J. Am. Chem. Soc. 2000, 122, 10991-10996. (k) Rivera, J. M.; Craig, S. L.; Martín, T.; Rebek, J. Angew. Chem., Int. Ed. 2000, 39, 2130-2132.
42. Some recent examples can be found in: (a) Conn, M. M.; Rebek, J. Chem. Rev. 1997, 97, 1647-1668. (b) Kikuchi, Y.; Tanaka, Y.; Sutarto, S.; Kobayashi, K.; Toi, H.; Aoyama, Y. J. Am. Chem. Soc. 1992, 114, 10302-10306. (c) Mammen, M.; Simanek, E. E.; Whitesides, G. M. J. Am. Chem. Soc. 1996, 118, 12614-12623. (d) Vreekamp, R. H.; Verboom, W.; Reinhoudt, D. N. J. Org. Chem. 1996, 61, 4282-4288. (e) Mogck, O.; Böhmer, V.; Vogt, W. Tetrahedron 1996, 52, 8489-8496. (f) Sessler, J. L.; Wang, R. J. Am. Chem. Soc. 1996, 118, 9808-9809. (g) Heinz, T.; Rudkevich, D. M.; Rebek, J. Nature 1998, 394, 764-767. (h) Martín, T.; Obst, U.; Rebek, J. Science 1998, 281, 1842-1845. (i) Prins, L. J.; Huskens, J.; de Jong, F.; Timmerman, P.; Reinhoudt, D. N. Nature 1999, 398, 498-502. (j) Hof, F.; Nuckolls, C.; Craig, S. L.; Martín, T.; Rebek, J. J. Am. Chem. Soc. 2000, 122, 10991-10996. (k) Rivera, J. M.; Craig, S. L.; Martín, T.; Rebek, J. Angew. Chem., Int. Ed. 2000, 39, 2130-2132.
43. Glusker, J. P. Top. Curr. Chem. 1998. 198, 1-56.
44. (a) Jeffrey, G. A. An Introduction to Hydrogen Bonding; Oxford University Press: New York, 1997.
45. (b) Israelachvili, J. Intermolecular & Surface Forces, 2nd ed.; Academic Press: London, 1992.
46. (a) For a general comment, see: Gellman, S. H. Chem. Rev. 1997, 97, 7, 1231-1232.
47. For examples of solvent effects on the strength of H bonds in complexes, see: (b) Kelly, T. R.; Kim, M. H. J. Am. Chem. Soc. 1994, 116, 7072-7080. (c) Ariga, K.; Anslyn, E. V. J. Org. Chem. 1992, 57, 417-419.
48. For examples of solvent effects on the strength of H bonds in complexes, see: (b) Kelly, T. R.; Kim, M. H. J. Am. Chem. Soc. 1994, 116, 7072-7080. (c) Ariga, K.; Anslyn, E. V. J. Org. Chem. 1992, 57, 417-419.
49. 3 has been reported by: Sessler, J. L.; Wang, R. W. Angew. Chem., Int. Ed. 1998, 37, 1726-1729.
50. For review articles on metal-templated self-assembly, see: (a) Fujita, M. Chem. Soc. Rev. 1998, 27, 417-426. (b) Stang, P. J. Chem. Eur. J. 1998, 4, 19-27. (c) Linton, B.; Hamilton, A. D. Chem. Rev. 1997, 97, 1669-1681. (d) Stang, P. J.; Olenyuk, B. Acc. Chem. Res. 1997, 30, 502-518.
51. For review articles on metal-templated self-assembly, see: (a) Fujita, M. Chem. Soc. Rev. 1998, 27, 417-426. (b) Stang, P. J. Chem. Eur. J. 1998, 4, 19-27. (c) Linton, B.; Hamilton, A. D. Chem. Rev. 1997, 97, 1669-1681. (d) Stang, P. J.; Olenyuk, B. Acc. Chem. Res. 1997, 30, 502-518.
52. For review articles on metal-templated self-assembly, see: (a) Fujita, M. Chem. Soc. Rev. 1998, 27, 417-426. (b) Stang, P. J. Chem. Eur. J. 1998, 4, 19-27. (c) Linton, B.; Hamilton, A. D. Chem. Rev. 1997, 97, 1669-1681. (d) Stang, P. J.; Olenyuk, B. Acc. Chem. Res. 1997, 30, 502-518.
53. For review articles on metal-templated self-assembly, see: (a) Fujita, M. Chem. Soc. Rev. 1998, 27, 417-426. (b) Stang, P. J. Chem. Eur. J. 1998, 4, 19-27. (c) Linton, B.; Hamilton, A. D. Chem. Rev. 1997, 97, 1669-1681. (d) Stang, P. J.; Olenyuk, B. Acc. Chem. Res. 1997, 30, 502-518.
54. For work on capsule formation in polar solvents based on the hetero association of oppositely charged ions, see for example: (a) Grawe, T.; Schrader, T.; Zadmard, R.; Kraft, A. J. Org. Chem. 2002, 67, 3755-3763. (b) Corbellini, F.; Flammengo, R.; Timmerman, P.; Crego-Calama, M.; Veslius, K.; Heck, A. J. R.; Luyten, I.; Reinhoudt, D. N. J. Am. Chem. Soc. 2002, 124, 65969-6575. (c) Fiammengo, R.; Timmerman, P.; de Jong, F.; Reinhoudt, D. N. Chem. Commun. 2000, 2313-2314. (d) Hamilin, B.; Jullien, L.; Derouet, C.; Hervé du Penhoat, C.; Berthault, P. J. Am. Chem. Soc. 1998. 120, 8438-8447. (e) Bok Lee, S.; Hong, J.-I. Tetrahedron Lett. 1996, 37, 8501-8504.
55. For work on capsule formation in polar solvents based on the hetero association of oppositely charged ions, see for example: (a) Grawe, T.; Schrader, T.; Zadmard, R.; Kraft, A. J. Org. Chem. 2002, 67, 3755-3763. (b) Corbellini, F.; Flammengo, R.; Timmerman, P.; Crego-Calama, M.; Veslius, K.; Heck, A. J. R.; Luyten, I.; Reinhoudt, D. N. J. Am. Chem. Soc. 2002, 124, 65969-6575. (c) Fiammengo, R.; Timmerman, P.; de Jong, F.; Reinhoudt, D. N. Chem. Commun. 2000, 2313-2314. (d) Hamilin, B.; Jullien, L.; Derouet, C.; Hervé du Penhoat, C.; Berthault, P. J. Am. Chem. Soc. 1998. 120, 8438-8447. (e) Bok Lee, S.; Hong, J.-I. Tetrahedron Lett. 1996, 37, 8501-8504.
56. For work on capsule formation in polar solvents based on the hetero association of oppositely charged ions, see for example: (a) Grawe, T.; Schrader, T.; Zadmard, R.; Kraft, A. J. Org. Chem. 2002, 67, 3755-3763. (b) Corbellini, F.; Flammengo, R.; Timmerman, P.; Crego-Calama, M.; Veslius, K.; Heck, A. J. R.; Luyten, I.; Reinhoudt, D. N. J. Am. Chem. Soc. 2002, 124, 65969-6575. (c) Fiammengo, R.; Timmerman, P.; de Jong, F.; Reinhoudt, D. N. Chem. Commun. 2000, 2313-2314. (d) Hamilin, B.; Jullien, L.; Derouet, C.; Hervé du Penhoat, C.; Berthault, P. J. Am. Chem. Soc. 1998. 120, 8438-8447. (e) Bok Lee, S.; Hong, J.-I. Tetrahedron Lett. 1996, 37, 8501-8504.
57. For work on capsule formation in polar solvents based on the hetero association of oppositely charged ions, see for example: (a) Grawe, T.; Schrader, T.; Zadmard, R.; Kraft, A. J. Org. Chem. 2002, 67, 3755-3763. (b) Corbellini, F.; Flammengo, R.; Timmerman, P.; Crego-Calama, M.; Veslius, K.; Heck, A. J. R.; Luyten, I.; Reinhoudt, D. N. J. Am. Chem. Soc. 2002, 124, 65969-6575. (c) Fiammengo, R.; Timmerman, P.; de Jong, F.; Reinhoudt, D. N. Chem. Commun. 2000, 2313-2314. (d) Hamilin, B.; Jullien, L.; Derouet, C.; Hervé du Penhoat, C.; Berthault, P. J. Am. Chem. Soc. 1998. 120, 8438-8447. (e) Bok Lee, S.; Hong, J.-I. Tetrahedron Lett. 1996, 37, 8501-8504.
58. For work on capsule formation in polar solvents based on the hetero association of oppositely charged ions, see for example: (a) Grawe, T.; Schrader, T.; Zadmard, R.; Kraft, A. J. Org. Chem. 2002, 67, 3755-3763. (b) Corbellini, F.; Flammengo, R.; Timmerman, P.; Crego-Calama, M.; Veslius, K.; Heck, A. J. R.; Luyten, I.; Reinhoudt, D. N. J. Am. Chem. Soc. 2002, 124, 65969-6575. (c) Fiammengo, R.; Timmerman, P.; de Jong, F.; Reinhoudt, D. N. Chem. Commun. 2000, 2313-2314. (d) Hamilin, B.; Jullien, L.; Derouet, C.; Hervé du Penhoat, C.; Berthault, P. J. Am. Chem. Soc. 1998. 120, 8438-8447. (e) Bok Lee, S.; Hong, J.-I. Tetrahedron Lett. 1996, 37, 8501-8504.
59. For examples of recent work on the importance of π-stacking in supramolecular aggregates, see for example: (a) Lahiri, S.; Thompson, J. L.; Moore, J. S. J. Am. Chem. Soc. 2000, 122, 11315-11319. (b) Sirish, M.; Schneider, H. J. J. Am. Chem. Soc. 2000, 122, 5881-5882. (c) Guckian, K. M.; Schweitzer, B. A.; Ren, R. X.-F.; Sheils, C. J.; Tahmassebi, D. C.; Kool, E. T. J. Am. Chem. Soc. 2000, 122, 2213-2222. (d) Isaacs, L.; Witt, D.; Fettinger, J. C. Chem. Commun. 1999, 2549-2550.
60. For examples of recent work on the importance of π-stacking in supramolecular aggregates, see for example: (a) Lahiri, S.; Thompson, J. L.; Moore, J. S. J. Am. Chem. Soc. 2000, 122, 11315-11319. (b) Sirish, M.; Schneider, H. J. J. Am. Chem. Soc. 2000, 122, 5881-5882. (c) Guckian, K. M.; Schweitzer, B. A.; Ren, R. X.-F.; Sheils, C. J.; Tahmassebi, D. C.; Kool, E. T. J. Am. Chem. Soc. 2000, 122, 2213-2222. (d) Isaacs, L.; Witt, D.; Fettinger, J. C. Chem. Commun. 1999, 2549-2550.
61. For examples of recent work on the importance of π-stacking in supramolecular aggregates, see for example: (a) Lahiri, S.; Thompson, J. L.; Moore, J. S. J. Am. Chem. Soc. 2000, 122, 11315-11319. (b) Sirish, M.; Schneider, H. J. J. Am. Chem. Soc. 2000, 122, 5881-5882. (c) Guckian, K. M.; Schweitzer, B. A.; Ren, R. X.-F.; Sheils, C. J.; Tahmassebi, D. C.; Kool, E. T. J. Am. Chem. Soc. 2000, 122, 2213-2222. (d) Isaacs, L.; Witt, D.; Fettinger, J. C. Chem. Commun. 1999, 2549-2550.
62. For examples of recent work on the importance of π-stacking in supramolecular aggregates, see for example: (a) Lahiri, S.; Thompson, J. L.; Moore, J. S. J. Am. Chem. Soc. 2000, 122, 11315-11319. (b) Sirish, M.; Schneider, H. J. J. Am. Chem. Soc. 2000, 122, 5881-5882. (c) Guckian, K. M.; Schweitzer, B. A.; Ren, R. X.-F.; Sheils, C. J.; Tahmassebi, D. C.; Kool, E. T. J. Am. Chem. Soc. 2000, 122, 2213-2222. (d) Isaacs, L.; Witt, D.; Fettinger, J. C. Chem. Commun. 1999, 2549-2550.
63. For a recent review on aromatic interactions, see: Hunter, C. A.; Lawson, K. R.; Perkins, J.; Urch, C. J. J. Chem. Soc., Perkin Trans. 2 2001, 651-669.
64. Schmuck, C. Chem. Eur. J. 2000, 6, 709-718.
65. Review articles on the binding of carboxylates by artificial hosts including guanidinium-based systems: (a) Fitzmaurice, R. J.; Kyne, G. M.; Douheret, D.; Kilburn, J. D. J. Chem. Soc., Perkin Trans. 1 2002, 841-864. (b) Schmidtchen, F. P.; Berger, M. Chem. Rev. 1997, 97, 1609-1646. (c) Schmidtchen, F. P. Artificial Anion Hosts: Concepts for Structure and Guest Binding. In Supramolecular Chemistry of Anions; Bianchi, A., Bowman-James, K., García-España, E., Eds.; Wiley-VCH: New York, 1997; pp 79-146. (d) Atwood, J. L.; Steed, J. W. Structural and Topological Aspects of Anion Coordination. In Supramolecular Chemistry of Anions; Bianchi, A., Bowman-James, K., García-España, E., Eds.; Wiley-VCH: New York, 1997; pp 147-216.
66. Review articles on the binding of carboxylates by artificial hosts including guanidinium-based systems: (a) Fitzmaurice, R. J.; Kyne, G. M.; Douheret, D.; Kilburn, J. D. J. Chem. Soc., Perkin Trans. 1 2002, 841-864. (b) Schmidtchen, F. P.; Berger, M. Chem. Rev. 1997, 97, 1609-1646. (c) Schmidtchen, F. P. Artificial Anion Hosts: Concepts for Structure and Guest Binding. In Supramolecular Chemistry of Anions; Bianchi, A., Bowman-James, K., García-España, E., Eds.; Wiley-VCH: New York, 1997; pp 79-146. (d) Atwood, J. L.; Steed, J. W. Structural and Topological Aspects of Anion Coordination. In Supramolecular Chemistry of Anions; Bianchi, A., Bowman-James, K., García-España, E., Eds.; Wiley-VCH: New York, 1997; pp 147-216.
67. Review articles on the binding of carboxylates by artificial hosts including guanidinium-based systems: (a) Fitzmaurice, R. J.; Kyne, G. M.; Douheret, D.; Kilburn, J. D. J. Chem. Soc., Perkin Trans. 1 2002, 841-864. (b) Schmidtchen, F. P.; Berger, M. Chem. Rev. 1997, 97, 1609-1646. (c) Schmidtchen, F. P. Artificial Anion Hosts: Concepts for Structure and Guest Binding. In Supramolecular Chemistry of Anions; Bianchi, A., Bowman-James, K., García-España, E., Eds.; Wiley-VCH: New York, 1997; pp 79-146. (d) Atwood, J. L.; Steed, J. W. Structural and Topological Aspects of Anion Coordination. In Supramolecular Chemistry of Anions; Bianchi, A., Bowman-James, K., García-España, E., Eds.; Wiley-VCH: New York, 1997; pp 147-216.
68. Review articles on the binding of carboxylates by artificial hosts including guanidinium-based systems: (a) Fitzmaurice, R. J.; Kyne, G. M.; Douheret, D.; Kilburn, J. D. J. Chem. Soc., Perkin Trans. 1 2002, 841-864. (b) Schmidtchen, F. P.; Berger, M. Chem. Rev. 1997, 97, 1609-1646. (c) Schmidtchen, F. P. Artificial Anion Hosts: Concepts for Structure and Guest Binding. In Supramolecular Chemistry of Anions; Bianchi, A., Bowman-James, K., García-España, E., Eds.; Wiley-VCH: New York, 1997; pp 79-146. (d) Atwood, J. L.; Steed, J. W. Structural and Topological Aspects of Anion Coordination. In Supramolecular Chemistry of Anions; Bianchi, A., Bowman-James, K., García-España, E., Eds.; Wiley-VCH: New York, 1997; pp 147-216.
69. Schmuck, C. Eur. J. Org. Chem. 1999, 2397-2403.
70. Schmuck, C. J. Org. Chem. 2000, 65, 2432-2437.
71. Schmuck, C. Tetrahedron 2001, 57, 3063-3067.
72. Synthesis of the starting material 3,4,5 -trimethyl-1H- pyrrole 2-carboxylic acid ethyl ester: (a) Paine, J. B., III; Dolphin, D. J. Org. Chem. 1985, 50, 5598-5604. (b) Cho, D. H.; Lee, J. H.; Kim, B. H. J. Org. Chem. 1999, 64, 8048-8050. Oxidation of 3,4,5-trimethyl-1H-pyrrole 2-carboxylic acid ethyl ester to acid 3: (c) Scarsella, M.; Sleiter, G. Gazz. Chim. Ital. 1988, 118, 757-762. (d) Paine, J. B., III; Dolphin, D. J. Org. Chem. 1988, 53, 2787-2795. (e) Eisner, U.; Lichtarowicz, A.; Linstead, R. P. J. Chem. Soc. 1957, 733-739. (f) Siedel, S. Liebigs Ann. Chem. 1943, 554, 144-159.
73. Synthesis of the starting material 3,4,5 -trimethyl-1H- pyrrole 2-carboxylic acid ethyl ester: (a) Paine, J. B., III; Dolphin, D. J. Org. Chem. 1985, 50, 5598-5604. (b) Cho, D. H.; Lee, J. H.; Kim, B. H. J. Org. Chem. 1999, 64, 8048-8050. Oxidation of 3,4,5-trimethyl-1H-pyrrole 2-carboxylic acid ethyl ester to acid 3: (c) Scarsella, M.; Sleiter, G. Gazz. Chim. Ital. 1988, 118, 757-762. (d) Paine, J. B., III; Dolphin, D. J. Org. Chem. 1988, 53, 2787-2795. (e) Eisner, U.; Lichtarowicz, A.; Linstead, R. P. J. Chem. Soc. 1957, 733-739. (f) Siedel, S. Liebigs Ann. Chem. 1943, 554, 144-159.
74. Synthesis of the starting material 3,4,5 -trimethyl-1H- pyrrole 2-carboxylic acid ethyl ester: (a) Paine, J. B., III; Dolphin, D. J. Org. Chem. 1985, 50, 5598-5604. (b) Cho, D. H.; Lee, J. H.; Kim, B. H. J. Org. Chem. 1999, 64, 8048-8050. Oxidation of 3,4,5-trimethyl-1H-pyrrole 2-carboxylic acid ethyl ester to acid 3: (c) Scarsella, M.; Sleiter, G. Gazz. Chim. Ital. 1988, 118, 757-762. (d) Paine, J. B., III; Dolphin, D. J. Org. Chem. 1988, 53, 2787-2795. (e) Eisner, U.; Lichtarowicz, A.; Linstead, R. P. J. Chem. Soc. 1957, 733-739. (f) Siedel, S. Liebigs Ann. Chem. 1943, 554, 144-159.
75. Synthesis of the starting material 3,4,5 -trimethyl-1H- pyrrole 2-carboxylic acid ethyl ester: (a) Paine, J. B., III; Dolphin, D. J. Org. Chem. 1985, 50, 5598-5604. (b) Cho, D. H.; Lee, J. H.; Kim, B. H. J. Org. Chem. 1999, 64, 8048-8050. Oxidation of 3,4,5-trimethyl-1H-pyrrole 2-carboxylic acid ethyl ester to acid 3: (c) Scarsella, M.; Sleiter, G. Gazz. Chim. Ital. 1988, 118, 757-762. (d) Paine, J. B., III; Dolphin, D. J. Org. Chem. 1988, 53, 2787-2795. (e) Eisner, U.; Lichtarowicz, A.; Linstead, R. P. J. Chem. Soc. 1957, 733-739. (f) Siedel, S. Liebigs Ann. Chem. 1943, 554, 144-159.
76. Synthesis of the starting material 3,4,5 -trimethyl-1H- pyrrole 2-carboxylic acid ethyl ester: (a) Paine, J. B., III; Dolphin, D. J. Org. Chem. 1985, 50, 5598-5604. (b) Cho, D. H.; Lee, J. H.; Kim, B. H. J. Org. Chem. 1999, 64, 8048-8050. Oxidation of 3,4,5-trimethyl-1H-pyrrole 2-carboxylic acid ethyl ester to acid 3: (c) Scarsella, M.; Sleiter, G. Gazz. Chim. Ital. 1988, 118, 757-762. (d) Paine, J. B., III; Dolphin, D. J. Org. Chem. 1988, 53, 2787-2795. (e) Eisner, U.; Lichtarowicz, A.; Linstead, R. P. J. Chem. Soc. 1957, 733-739. (f) Siedel, S. Liebigs Ann. Chem. 1943, 554, 144-159.
77. Synthesis of the starting material 3,4,5 -trimethyl-1H- pyrrole 2-carboxylic acid ethyl ester: (a) Paine, J. B., III; Dolphin, D. J. Org. Chem. 1985, 50, 5598-5604. (b) Cho, D. H.; Lee, J. H.; Kim, B. H. J. Org. Chem. 1999, 64, 8048-8050. Oxidation of 3,4,5-trimethyl-1H-pyrrole 2-carboxylic acid ethyl ester to acid 3: (c) Scarsella, M.; Sleiter, G. Gazz. Chim. Ital. 1988, 118, 757-762. (d) Paine, J. B., III; Dolphin, D. J. Org. Chem. 1988, 53, 2787-2795. (e) Eisner, U.; Lichtarowicz, A.; Linstead, R. P. J. Chem. Soc. 1957, 733-739. (f) Siedel, S. Liebigs Ann. Chem. 1943, 554, 144-159.
78. According to a similar approach by: Baciocchi. E.; Muraglia, E.; Sleiter, G. J. Org. Chem. 1992, 57, 2486-2490.
79. Zapf, C. W.; Creighton, C. J.; Tomioka, M.; Goodman, M. Org. Lett. 2001, 3, 1133-1136.
80. Schmuck, C.; Geiger, L.; Schwegmann, M. 2001, unpublished results.
81. As neither in the positive ion mode nor for the unsubstituted parent zwitterion 1 could any signals be detected in the ESI mass spectrum, deprotonation probably takes place at the terminal OH group of one of the triethylene glycol chains in the case 2. Hence, the binding motif itself is not affected by this deprotonation.
82. Dixon, R. D.; Geib, S. J.; Hamilton, A. D. J. Am. Chem. Soc. 1992, 114, 365-366.
83. a of 4.6.
84. c/d and therefore less capable to stabilize the guanidinium cation as its electron density is lower. See also ref 27.
85. (a) Wilcox, C. S. In Frontiers in Supramolecular Chemistry and Photochemistry; Schneider, H. J., Dürr, H., Eds.; VCH: Weinheim, 1990; pp 123-144. (b) Connors, K. A. Binding Constants; Wiley: New York, 1987.
86. (a) Wilcox, C. S. In Frontiers in Supramolecular Chemistry and Photochemistry; Schneider, H. J., Dürr, H., Eds.; VCH: Weinheim, 1990; pp 123-144. (b) Connors, K. A. Binding Constants; Wiley: New York, 1987.
87. (a) Bangerter, B. W.; Chan, S. I. J. Am. Chem. Soc. 1969, 91, 3910-3921.
88. (b) Davis, J. C., Jr.; Deb, K. K. Adv. Magn. Reson. 1970, 4, 201-270.
89. For a general discussion of chain-association equilibria studies by NMR, see: (c) LaPlanche, L. A.; Thompson, H. B.; Rogers, M. T. J. Phys. Chem. 1965, 69, 1482-1488.
90. With a DMSO concentration of <2.5%, the properties of the solvent mixture are hardly affected by its presence as the more polar component y(water) is already present in a large excess. Therefore, it is not expected that an additional increase of the water content from 97.5 to 100% further affects the stability of the supramolecular aggregate.
91. Horvath. P.; Gergely, A.; Noszal, B. J. Chem. Soc., Perkin Trans. 2 1996, 1419-1422.
92. Hossain, M. A.; Schneider, H.-J. Chem. Eur. J. 1999, 5, 1284-1290.
93. Schneider, H.-J. Chem. Soc. Rev. 1994, 22, 227-234.
94. Dietrich, B.; Fryles, D. L.; Fryles, T. M.; Lehn, J.-M. Helv. Chim. Acta 1979, 62, 2763-2787.
95. (a) Jorgensen, W. L.; Pranata, J. J. Am. Chem. Soc. 1990, 112, 2008-2010.
96. (b) Pranata, J.; Wierschke, S. G.; Jorgensen, W. L. J. Am. Chem. Soc. 1990, 112, 2810-2819.
97. (a) Galàn, A.; deMendoza, J. Top. Curr. Chem. 1995, 175, 101-132.
98. (b) Goswami, S.; Ghosh, K.; Dasgupta, S. Tetrahedron 1996, 52, 12223-12232.
99. (c) König, B.; Möller, O.; Bubenitschek, P. J. Org. Chem. 1995, 60, 4291-4293.
100. (d) Yang, J.; Fan, E.; Geib, S. J.; Hamilton, A. D. J. Am. Chem. Soc. 1993, 115, 5314-5315.
101. (e) Garcia-Tellado, F.; Goswami, S.; Chang, S. K.; Geib, S. J.; Hamilton, A. D. J. Am. Chem. Soc. 1990, 112, 7393-7394.
102. (f) Etter, M. C.; Adsmond, D. A. J. Chem. Soc., Chem. Commun. 1990, 589-590.
103. Reichardt, C. Solvents and Solvent Effects in Organic Chemistry: VCH: Weinheim, 1990.
104. Bianchi, A. Thermodynamics of Anion Complexation. In Supramolecular Chemistry of Anions: Bianchi, A., Bowman-James, K., García-España. E., Eds.; Wiley-VCH: New York, 1997; pp 217-276.