Weak Intermolecular Interactions and Molecular Recognition: Structure and Dynamics of the Benzene and Pyridine p-tert-Butylcalix[4]arene Inclusions

Journal of Physical Chemistry B

Volumn 103, Issue 48, 1999, Pages 10604-10616

  Brouwer, Eric B ^a,b   Enright, Gary D ^a   Ratcliffe, Christopher I ^a   Facey, Glenn A ^a,b   Ripmeester, John A ^a,b  

^a NATIONAL RESEARCH COUNCIL CANADA   (Canada)

^b CARLETON UNIVERSITY   (Canada)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0033518339     PISSN: 15206106     EISSN: None     Source Type: Journal    
DOI: 10.1021/jp9921598     Document Type: Article

References (72)

1. (a) Marassi, F. M.; Ramamoorthy, A.; Opella, S. J. Proc. Natl. Acad. Sci. U.S.A. 1997, 94, 8551.
2. (b) Marassi, F. M.; Opella, S. J. Curr. Opinion Struct. Biol. 1998, 8, 640.
3. (c) Kim, Y.; Valentine, K.; Opella, S. J.; Schendel, S. L.; Cramer, W. A. Protein Sci. 1998, 7, 342.
4. (d) Hu, J. Z.; Facelli, J. C.; Alderman, D. W.; Pugmire, R. J.; Grant, D. M. J. Am. Chem. Soc. 1998, 120, 9863.
5. (a) Brouwer, E. B.; Enright, G. D.; Ripmeester, J. A. Supramol. Chem. 1996, 7, 79.
6. (b) Brouwer, E. B.; Enright, G. D.; Ripmeester, J. A. Chem. Commun. 1997, 939.
7. (c) Brouwer, E. B.; Enright, G. D.; Ripmeester, J. A. J. Am. Chem. Soc. 1997, 119, 5404.
8. (d) Brouwer, E. B.; Udachin, K.; Enright, G. D.; Ratcliffe, C. I.; Ripmeester, J. A. Chem. Commun. 1998, 587.
9. (a) Gutsche, C. D. Calixarenes; RSC: Cambridge, 1989.
10. (b) Vicens, J., Bohmer, V., Eds. Calixarenes; Kluwer: Dordrecht, 1990.
11. (c) Ungaro, R.; Arduini, A.; Casnati, A.; Ori, O.; Pochini, A.; Ugozzoli, F. Complexation of Ions and Neutral Molecules by Functionalized Calixarenes. In Computational Approaches in Supramolecular Chemistry; Wipff, G., Ed.; NATO ASIC426; Kluwer: Dordrecht, 1994; p 277.
12. (d) Bohmer, V. Angew. Chem., Int. Ed. Engl. 1995, 34, 713.
13. (a) Andreetti, G. D.; Ungaro, R.; Pochini, A. J. Chem. Soc., Chem. Commun. 1979, 1005.
14. (b) Ungaro, R.; Pochini, A.; Andreetti, G. D.; Domiano, P. J. Chem. Soc., Perkin Trans. 2 1985, 197.
15. Andreetti, G. D.; Ori, O.; Ugozzoli, F.; Alfieri, C.; Pochini, A.; Ungaro, R. J. Inclusion Phenom. 1988, 6, 523.
16. (a) Takeshita, M.; Nishio, S.; Shinkai, S. J. Org. Chem. 1994, 59, 4032.
17. (b) Xu, W.; Puddephatt, R. J.; Muir, K. W.; Torabi, A. A. Organometallics 1994, 13, 3054.
18. (c) Masci, B. Tetrahedron 1995, 51, 5459.
19. (d) Wipff, G.; Lauterbach, M. Supramol. Chem. 1995, 6, 187.
20. (e) Koh, K. N.; Araki, K.; Ideka, A.; Otsuka, H.; Shinkai, S. J. Am. Chem. Soc. 1996, 118, 755.
21. (f) Lhoták, P.; Shinkai, S. J. Phys. Org. Chem. 1997, 10, 273.
22. Brouwer, E. B.; Ripmeester, J. A.; Enright, G. D. J. Inclusion Phenom. 1996, 24, 1.
23. Desiraju, G. Acc. Chem. Res. 1996, 29, 441.
24. (a) Ozin, G. A. Adv. Mater. 1992, 4, 612.
25. (b) Monnier, A.; Schuth, F.; Huo, Q.; Kumar, D.; Margolese, D.; Maxwell, R. S.; Stucky, G. D.; Krishnamurty, M.; Petroff, P.; Firouzi, A.; Janicke, M.: Chmelka, B. F. Science 1993, 261, 1299.
26. (c) Huo, Q.; Margolese, D. I.; Ciesla, U.; Feng, P.; Gier, T. E.; Sieger, P.; Leon, R.; Petroff, P. M.; Schuth, F.; Stucky, G. D. Nature 1994, 368, 317.
27. (d) Yang, H.; Kuperman, A.; Coombs, N.; Mamiche-Afara, S.; Ozin, G. A. Nature 1996, 379, 703.
28. (a) Lehn, J.-M. Angew. Chem., Int. Ed. Engl. 1990, 29, 1304.
29. (b) Atwood, J. L., Davies, J. E. D., MacNicol, D. D., Vogtle, F., Eds. Comprehensive Supramolecular Chemistry; Pergammon/Elsevier: Oxford, 1996; Vols. 1 and 2.
30. (c) Mallouk, T. E.; Gavin, J. A. Acc. Chem. Res. 1998, 31, 209.
31. (a) Andreetti, G. D.; Ugozzoli, F.; Nakamoto, Y.; Ishida, S. J. Inclusion Phenom. 1991, 11, 241.
32. (b) Gutsche, C. D.; Gutsche, A. E.; Karaulov, A. I. J. Inclusion Phenom. 1985, 3, 447.
33. (c) Czugler, M.; Tisza, S.; Speier, G. J. Inclusion Phenom. 1991, 11, 323.
34. Davis, J. H.; Jeffrey, K. R.; Bloom, M.; Valic, M. I.; Higgs, T. P. Chem. Phys. Lett. 1976, 42, 390.
35. Gabe, E. J.; Le Page, Y.; Charland, J. P.; Lee, F. L.; White, P. S. J. Appl. Crystallogr. 1989, 22, 384.
36. (a) Komoto, T.; Ando, I.; Nakamoto, Y.; Ishida, S. J. Chem. Soc., Chem. Commun. 1988, 135.
37. (b) Facey, G. A.; Dubois, R. H.; Zakrzewski, M.; Ratcliffe, C. I.; Atwood, J. L.; Ripmeester, J. A. Supramol. Chem. 1993, 1, 199.
38. Brouwer, E. B.; Enright, G. D.; Ripmeester, J. A. Supramol. Chem. 1996, 7, 143.
39. Opella, S. J.; Frey, M. H. J. Am. Chem. Soc. 1979, 101, 5854. Delay before acquisition = 40 μs.
40. Schatz, J.; Schildbach, F.; Lentz, A.; Rastätter, S. J. Chem. Soc., Perkin Trans. 2 1998, 75.
41. (a) Cohen, M. H.; Reif, F. Solid State Phys. 1957, 5, 321-438.
42. (b) Barnes, R. G. Adv. Nucl. Quad. Reson. 1974, 1, 335.
43. Greenfield, M. S.; Ronemus, A. D.; Void, R. L.; Void, R. R.; Ellis, P. D.; Raidy, T. E. J. Magn. Reson. 1987, 72, 89.
44. (a) Spiess, H. W.; Sillescu, H. J. Magn. Reson. 1981, 42, 381-389.
45. (b) Vega, A. J.; Luz, J. J. Chem. Phys. 1987, 86, 1803.
46. Wittebort, R. J.; Olejniczak, E. T.; Griffin, R. G. J. Chem. Phys. 1987, 86, 5411.
47. Ratcliffe, C. I. J. Phys. Chem. 1987, 91, 6464.
48. Facey, G. A.; Ratcliffe, C. I.; Ripmeester, J. A. J. Phys. Chem. 1995, 99, 12249.
49. (a) Ok, J. H.; Vold, R. R.; Void, R. L. J. Phys. Chem. 1989, 93, 7618.
50. (b) Nishikiori, S.; Ratcliffe, C. I.: Ripmeester, J. A. J. Phys. Chem. 1991, 95, 1589.
51. (c) Aliev, A. E.; Harris, K. D. M.; Guillaume, F. J. Phys. Chem. 1995, 99, 1156.
52. (d) Hall, L. D.; Lim, T. K. J. Am. Chem. Soc. 1986, 108, 2503.
53. (e) Meirovitch, E.; Belsky, I.; Vega, S. J. Phys. Chem. 1984, 88, 1522.
54. (f) Chopra, N.; Chapman, R. G.; Chuang, Y.-F.; Sherman, J. C.; Burnell, E. E.; Polson, J. M. J. Chem. Soc.; Faraday Trans. 1995, 91, 4127.
55. Barnes, R. G.; Bloom, J. W. J. Chem. Phys. 1972, 57, 3082.
56. Aliev, A. E.; Harris, K. D. M.; Mahdyarfar, A. J. Chem. Soc., Faraday Trans. 1995, 91, 2017.
57. Brunie, S.; Navaza, A.; Tsoucaris, G.; Declercq, J. P.; Germain, G. Acta Crystallogr. 1977, B33, 2645.
58. Bak, B.; Hansen-Nygaard, L.; Rastrup-Andersen, J. J. Mol. Spectrosc. 1958, 2, 361.
59. Facelli, J. C.; Pugmire, R. J.; Grant, D. M. J. Am. Chem. Soc. 1996, 118, 5488.
60. Solum, M. S.; Altmann, K. L.; Strohmeier, M.; Berges, D. A.; Zhang, Y.; Facelli, J. C.; Pugmire, R. J.; Grant, D. M. J. Am. Chem. Soc. 1997, 119, 9804.
61. (a) Jameson, A. K.; Moyer, J.; Jameson, C. J. J. Chem. Phys. 1978, 68, 2873.
62. (b) Witanowski, M.; Stefaniak, L.; Webb, G. A. Nitrogen NMR Spectroscopy. Annu. Rep. NMR Spectrosc. 1993, 25, 2.
63. Spinning rates: v = 3654, 2184, 1959, and 1743 ± 3 Hz. The spectra were processed (3K points zero-filled to 4K.; line broadening = 50 Hz) and the spectra corrected to give a flat baseline. The isotropic line was identified and fitted for line width, chemical shift position, and intensity. Next, the spinning sidebands were identified and then fitted for intensity using the Herzfeld-Berger method (Herzfeld, J.; Berger, A. E. J. Chem. Phys. 1980, 73, 6021). Finally the spinning speed was optimized to match the experiment sideband positions with the model. The fitting proceeded iteratively, and after the final iteration, each peak was examined visually to ensure an acceptable fit. The chemical shift tensor components were determined from a least-squares fit of the modeled spectra.
64. Schweitzer, D.; Spiess, H. W. J. Magn. Reson. 1974, 15, 529.
65. 5 indicate pyridine is static from 77 K to its melting point at 231 K.
66. We do not report H⋯N distances since the hydrogen atoms were placed in calculated positions due to the tert-butyl group disorder.
67. Nelson, R. D.; Lide, D. R.; Maryott, A. A. Handbook of Chemistry and Physics, 64th ed.; CRC Press: Boca Raton, FL, 1983; p E61.
68. Fujimoto, T.; Yanagihara, R.; Kobayashi, K.; Aoyama, Y. Bull. Chem. Soc. Jpn. 1995, 68, 2113.
69. Mascal, M. Chem. Commun. 1998, 303.
70. (a) Duthaler, R. O.; Roberts, J. D. J. Am. Chem. Soc. 1978, 100, 4969.
71. (b) Denisov, G. S.; Gindin, V. A.; Golubev, N. S.; Ligay, S. S.; Shchepkin, D. N.; Smirnov, S. N. J. Mol. Liquids 1995, 67, 217.
72. Mason, J. Solid State Nucl. Magn. Reson. 1993, 2, 285.