Characterization of self-assembling encapsulation complexes in the gas phase and solution

Journal of the American Chemical Society

Volumn 121, Issue 10, 1999, Pages 2133-2138

  Schalley, Christoph A ^a,b   Martín, Tomás ^a,c   Obst, Ulrike ^a,b   Rebek Jr , Julius ^a  

^a SCRIPPS RESEARCH INSTITUTE   (United States)

^b Deutsche Akad Naturforscher L ^*

^c Min de Educ y Cultura of Spain   (Spain)

Author keywords

[No Author keywords available]

Indexed keywords

ARTICLE; CHEMICAL STRUCTURE; COMPLEX FORMATION; ENCAPSULATION; HYDROGEN BOND; MASS SPECTROMETRY; MOLECULAR DYNAMICS; MOLECULAR INTERACTION; NUCLEAR MAGNETIC RESONANCE; PHYSICAL CHEMISTRY; STEREOCHEMISTRY;

EID: 0033577280     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja9836848     Document Type: Article

References (78)

1. Przybylski, M.; Glocker, M. O. Angew. Chem., Int. Ed. Engl. 1996, 35, 806.
2. (a) Smith, R. D.; Loo, J. A.; Ogorzalek-Loo, R. R.; Busman, M.; Udseth, H. R. Mass Spectrom. Rev. 1991, 10, 359.
3. (b) Light-Wahl, K. J.; Schwartz, B. L.; Smith, R. D. J. Am. Chem. Soc. 1994, 116, 5271.
4. (c) Kriwacki, R. W.; Wu, J.; Siuzdak, G.; Wright, P. E. J. Am. Chem. Soc. 1996, 118, 5320.
5. (d) Loo, J. A. Mass Spectrom. Rev. 1997, 16, 1.
6. (a) Ganem, B.; Li, Y.-T.; Henion, J. D. J. Am. Chem. Soc. 1991, 113, 6294.
7. (b) Ganem, B.; Li, Y.-T.; Henion, J. D. J. Am. Chem. Soc. 1991, 113, 7878.
8. (c) Cheng, X.; Chen, R.; Bruce, J. E.; Schwartz, B. L.; Anderson, G. A.; Hofstadler, S. A.; Gale, D. C.; Smith, R. D.; Gao, J.; Sigal, G. B.; Mammen, M.; Whitesides, G. M. J. Am. Chem. Soc. 1995, 117, 8859.
9. (a) Gale, D. C.; Goodlett, D. R.; Light-Wahl, K. J.; Smith, R. D. J. Am. Chem. Soc. 1994, 116, 6027.
10. (b) Ganem, B.; Li, Y.-T.; Hsieh, Y.-L.; Henion, J. D.; Kaboord, B. F.; Frey, M. W.; Benkovic, S. J. J. Am. Chem. Soc. 1994, 116, 1352.
11. (c) Cheng, X.; Harms, A. C.; Goudreau, P. N.; Terwilliger, T. C.; Smith, R. D. Proc. Natl. Acad. Sci. U.S.A. 1996, 93, 7022.
12. (a) Wilson, S. R.; Yasmin, A.; Wu, Y. J. Org. Chem. 1992, 57, 6941.
13. (b) Hopfgartner, G.; Piguet, C.; Henion, J. D.; Williams, A. F. Helv. Chim. Acta 1993, 76, 1759.
14. (c) Leize, E.; Van Dorsselaer, A.; Kraemer, R.; Lehn, J.-M. J. Chem. Soc., Chem. Commun. 1993, 990.
15. (d) Piguet, C.; Hopfgartner, G.; Bocquet, B.; Schaad, O.; Williams, A. F. J. Am. Chem. Soc. 1994, 116, 9092.
16. (e) Bakhtiar, R.; Chen, H.; Ogo, S.; Fish, R. H. Chem. Commun. 1997, 2135.
17. (f) Funeriu, D. P.; Lehn, J.-M.; Baum, G.; Fenske, D. Chem. Eur. J. 1997, 3, 99.
18. (g) Stang, P. J.; Cao, D. H.; Chen, K.; Gray, G. M.; Muddiman, D. C.; Smith, R. C. J. Am. Chem. Soc. 1997, 119, 5163.
19. (h) Manna, J.; Kuehl, C. J.; Whiteford, J. A.; Stang, P. J.; Muddiman, D. C.; Hofstadler, S. A.; Smith, R. D. J. Am. Chem. Soc. 1997, 119, 11611.
20. (i) Jacopozzi, P.; Dalcanale, E. Angew. Chem., Int. Ed. Engl. 1997, 36, 613.
21. (a) Bitsch, F.; Dietrich-Buchecker, C. O.; Khemiss, A.-K.; Sauvage, J.-P.; Van Dorsselaer, A. J. Am. Chem. Soc. 1991, 113, 4023.
22. (b) Ashton, P. R.; Brown, C. L.; Chapman, J. R.; Gallagher, R. T.; Stoddart, J. F. Tetrahedron Lett. 1992, 32, 7771.
23. (c) Ashton, P. R.; Matthews, O. A.; Menzer, S.; Raymo, F. M.; Spencer, N.; Stoddart, J. F.; Willams, D. J. Liebigs Ann./Recl. 1997, 2485.
24. (a) Vicenti, M.; Pelizzetti, E.; Dalcanale, E.; Soncini, P. Pure Appl. Chem. 1993, 65, 1507.
25. (b) Vicenti, M.; Minero, C.; Pelizzetti, E.; Secchi, A.; Dalcanale, E. Pure Appl. Chem. 1995, 67, 1075.
26. (c) Vicenti, M. J. Mass Spectrom. 1995, 30, 925.
27. For example, see: (a) Vicenti, M.; Dalcanale, E.; Soncini, P.; Guglielmetti, G. J. Am. Chem. Soc. 1990, 112, 445. (b) Vicenti, M.; Dalcanale, E., Proceedings of the 44th ASMS Conference on Mass Spectrometry and Allied Topics; Portland, Oregon, 1996; p 413.
28. For example, see: (a) Vicenti, M.; Dalcanale, E.; Soncini, P.; Guglielmetti, G. J. Am. Chem. Soc. 1990, 112, 445. (b) Vicenti, M.; Dalcanale, E., Proceedings of the 44th ASMS Conference on Mass Spectrometry and Allied Topics; Portland, Oregon, 1996; p 413.
29. Siuzdak, G.; Bothner, B. Angew. Chem., Int. Ed. Engl. 1995, 34, 2053.
30. (a) Lamcharfi, E.; Chuilon, S.; Kerbal, A.; Kunesch, G.; Libot, F.; Virelizier, H. J. Mass Spectrom. 1996, 31, 982.
31. Also, see: (b) Siuzdak, G.; Ichikawa, Y.; Muñoz, B.; Caulfield, T. J.; Wong, C.-H.; Nicolaou, K. C. J. Am. Chem. Soc. 1993, 115, 2877.
32. (a) Siuzdak, G.; Bothner, B.; Yeager, M.; Brugidou C.; Fauquet, C. M.; Hoey, K.; Chang, C.-M. Chem. Bull. 1996, 5, 45.
33. (b) Siuzdak, G. J. Mass Spectrom. 1998, 33, 203.
34. (a) Russell, K. C.; Leize, E.; Van Dorsselaer, A.; Lehn; J.-M. Angew. Chem., Int. Ed. Engl. 1995, 34, 209.
35. (b) Cheng, X.; Gao, Q.; Smith, R. D.; Simanek, E. E.; Mammen, M.; Whitesides, G. M. J. Org. Chem. 1996, 61, 2204.
36. (c) Jolliffe, K. A.; Crego Calama, M.; Fokkens, R.; Nibbering, N. M. M.; Timmerman, P.; Reinhoudt, D. N. Angew. Chem., Int. Ed. Engl. 1998, 37, 1247.
37. (d) Schnier, P. D.; Klassen, J. S.; Strittmatter, E. F.; Williams, E. R. J. Am. Chem. Soc. 1998, 120, 9605.
38. (e) Scherer, M.; Sessler, J. L.; Moini, M.; Gebauer, A.; Lynch, V. Chem. Eur. J. 1998, 4, 152.
39. (a) Branda, N.; Grotzfeld, R. M.; Valdés, C.; Rebek, J., Jr. J. Am. Chem. Soc. 1995, 117, 85.
40. (b) Meissner, R. S.; Rebek, J., Jr.; de Mendoza, J. Science 1995, 270, 1485.
41. (c) Meissner, R.; Garcias, X.; Mecozzi, S.; Rebek, J., Jr. J. Am. Chem. Soc. 1997, 119, 77.
42. (d) Rivera, J. M.; Martín, T.; Rebek, J., Jr. J. Am. Chem. Soc. 1998, 120, 819.
43. For reviews, see: (e) Rebek, J., Jr. Chem. Soc. Rev. 1996, 255. (f) Conn, M. M.; Rebek, J., Jr. Chem. Rev. 1997, 97, 1647. (g) de Mendoza, J. Chem. Eur. J. 1998, 4, 1373.
44. For reviews, see: (e) Rebek, J., Jr. Chem. Soc. Rev. 1996, 255. (f) Conn, M. M.; Rebek, J., Jr. Chem. Rev. 1997, 97, 1647. (g) de Mendoza, J. Chem. Eur. J. 1998, 4, 1373.
45. For reviews, see: (e) Rebek, J., Jr. Chem. Soc. Rev. 1996, 255. (f) Conn, M. M.; Rebek, J., Jr. Chem. Rev. 1997, 97, 1647. (g) de Mendoza, J. Chem. Eur. J. 1998, 4, 1373.
46. Schalley, C. A.; Rivera, J. M.; Martin, T.; Santamaría, J.; Siuzdak, G.; Rebek, J., Jr. Eur. J. Org. Chem., in press.
47. (a) Fenn, J. B.; Mann, M.; Meng, C. K.; Wong, S. F.; Whitehouse, C. M. Mass Spectrom. Rev. 1990, 9, 37.
48. (b) Kebarle, P.; Tang, L. Anal. Chem. 1993, 65, 972A.
49. (c) Gaskell, S. J. J. Mass Spectrom. 1997, 32, 677.
50. (d) Electrospray Ionisation Mass Spectrometry; Cole, R. B., Ed.; Wiley: New York, 1997.
51. Martín, T.; Obst, U.; Rebek, J., Jr. Science 1998, 281, 1842.
52. (a) Mohamadi, F.; Richards, N. G.; Guida, W. C.; Liskamp, R.; Caufield, C.; Chang, G.; Hendrickson, T.; Still, W. C. J. Comput. Chem. 1990, 11, 440.
53. (b) McDonald, D. Q.; Still, W. C. Tetrahedron Lett. 1992, 33, 7743.
54. Nicholls, A.; Sharp, K. A.; Honig, B. Proteins 1991, 11, 281.
55. Mecozzi, S.; Rebek, J., Jr. Chem. Eur. J. 1998, 4, 1016.
56. For example, see: (a) Loo, J. A.; Ogorzalek-Loo, R. R.; Udseht, H. R.; Edmonds, C. G.; Smith, R. D. Rapid Commun. Mass Spectrom. 1991, 5, 582. (b) Guevremont, R.; Siu, K. W. M.; Le Blanc, J. C. Y.; Berman, S. S. J. Am. Soc. Mass Spectrom. 1992, 3, 216. (c) Clemmer, D. E.; Hudgins, R. R.; Jorrold, M. F. J. Am. Chem. Soc. 1995, 117, 10141.
57. For example, see: (a) Loo, J. A.; Ogorzalek-Loo, R. R.; Udseht, H. R.; Edmonds, C. G.; Smith, R. D. Rapid Commun. Mass Spectrom. 1991, 5, 582. (b) Guevremont, R.; Siu, K. W. M.; Le Blanc, J. C. Y.; Berman, S. S. J. Am. Soc. Mass Spectrom. 1992, 3, 216. (c) Clemmer, D. E.; Hudgins, R. R.; Jorrold, M. F. J. Am. Chem. Soc. 1995, 117, 10141.
58. For example, see: (a) Loo, J. A.; Ogorzalek-Loo, R. R.; Udseht, H. R.; Edmonds, C. G.; Smith, R. D. Rapid Commun. Mass Spectrom. 1991, 5, 582. (b) Guevremont, R.; Siu, K. W. M.; Le Blanc, J. C. Y.; Berman, S. S. J. Am. Soc. Mass Spectrom. 1992, 3, 216. (c) Clemmer, D. E.; Hudgins, R. R.; Jorrold, M. F. J. Am. Chem. Soc. 1995, 117, 10141.
59. For previous examples for the encapsulation of ammonium ions, see: (a) Caulder, D. L.; Powers, R. E.; Parac, T. N.; Raymond, K. N. Angew. Chem., Int. Ed. Engl. 1998, 37, 1840. (b) Parac, T. N.; Caulder, D. L.; Raymond, K. N. J. Am. Chem. Soc. 1998, 120, 8003. (c) Murayame, K.; Aoki, K. Chem. Commun. 1998, 607.
60. For previous examples for the encapsulation of ammonium ions, see: (a) Caulder, D. L.; Powers, R. E.; Parac, T. N.; Raymond, K. N. Angew. Chem., Int. Ed. Engl. 1998, 37, 1840. (b) Parac, T. N.; Caulder, D. L.; Raymond, K. N. J. Am. Chem. Soc. 1998, 120, 8003. (c) Murayame, K.; Aoki, K. Chem. Commun. 1998, 607.
61. For previous examples for the encapsulation of ammonium ions, see: (a) Caulder, D. L.; Powers, R. E.; Parac, T. N.; Raymond, K. N. Angew. Chem., Int. Ed. Engl. 1998, 37, 1840. (b) Parac, T. N.; Caulder, D. L.; Raymond, K. N. J. Am. Chem. Soc. 1998, 120, 8003. (c) Murayame, K.; Aoki, K. Chem. Commun. 1998, 607.
62. (a) Rebek, J., Jr. Acc. Chem. Res. 1984, 17, 258.
63. (b) Connors, K. A., Binding Constants - The Measurement of Molecular Complex Stability; Wiley: New York, 1987.
64. (c) Tabushi, I. Pure Appl. Chem. 1988, 60, 581.
65. (d) Nabeshima, T. Coord. Chem. Rev. 1996, 148, 151.
66. (e) Bisson, A. P.; Hunter, C. A.; Morales, J. C. Young, K. Chem. Eur. J. 1998, 4, 845.
67. (f) Nabeshima, T.; Takahashi, T.; Hanami, T.; Kikuchi, A.; Kawabe, T.; Yano, Y. J. Org. Chem. 1998, 63, 3802.
68. (a) Valdés, C.; Spitz, U. P.; Toledo, L. M.; Kubik, S. W.; Rebek, J., Jr. J. Am. Chem. Soc. 1995, 117, 12733.
69. (b) Mogck, O.; Böhmer, V.; Vogt, W. Tetrahedron 1996, 52, 8489.
70. The slight deviation from the statistical distribution may be due to discrimination of lower masses by the MS detection system.
71. 2 groups. Therefore, the packing coefficients should be considered as a rough estimate rather than exact numbers.
72. (a) Dougherty, D. A. Science 1996, 271, 163.
73. (b) Ma, J. C.; Dougherty, D. A. Chem. Rev. 1997, 97, 1303.
74. (c) Lhoták, P.; Shinkai, S. J. Phys. Org. Chem. 1997, 10, 273.
75. Also, see: (d) Claessens, C. G.; Stoddart, J. F. J. Phys. Org. Chem. 1997, 10, 254.
76. Other forces, e.g. ion-dipole interactions, may play a role. However, none of the dipoles in the cavity walls are directed with the negative partial charge toward the encapsulated cation; rather, they are tangential to the capsule walls. Therefore, we believe these interactions to be small and the cation-π interaction to be the major contribution.
77. Ting, A. Y.; Shin, I.; Lucero, C.; Schultz, P. G. J. Am. Chem. Soc. 1998, 120, 7135.
78. 16