Sterically controlled architectural reversion in hydrogen-bonded crystalline clathrates

Journal of the American Chemical Society

Volumn 121, Issue 2, 1999, Pages 320-325

  Evans, Cara C ^a   Sukarto, Lisa ^a   Ward, Michael D ^a  

^a University of Minnesota   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ANION; AZOBENZENE DERIVATIVE; CATION; CLATHRIN; GUANIDINE DERIVATIVE; SULFONIC ACID DERIVATIVE;

ARTICLE; CRYSTAL STRUCTURE; HYDROGEN BOND; SOLID STATE; STEREOCHEMISTRY;

EID: 0033585541     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja983122o     Document Type: Article

References (39)

1. Gavezzotti, A. Acc. Chem. Res. 1994, 27, 309-314.
2. Bishop, R. Chem. Soc. Rev. 1996, 311-319.
3. (a) Fujita, M.; Kwon, Y. J.; Sasaki, O.; Yamaguchi, K.; Ogura, K. J. Am. Chem. Soc. 1995, 117, 7287-7288.
4. (b) Ermer, O. J. Am. Chem. Soc. 1988, 110, 3747-3754.
5. (c) Venkataraman, D.; Lee, S.; Zhang, J.; Moore, J. S. Nature 1994, 371, 591-593.
6. (d) Melendez, R. E.; Sharma, C. V. K.; Zaworotko, M. J.; Bauer, C.; Rogers, R. D. Angew. Chem., Int. Ed. Engl. 1996, 35, 2213-2215.
7. (e) Yaghi, O. M.; Davis, C. E.; Li, G.; Li, H. J. Am. Chem. Soc. 1997, 119, 2861-2868.
8. (f) Brunet, P.; Simard, M.; Wuest, J. D. J. Am. Chem. Soc. 1997, 119, 2737-2738.
9. (g) Kololuchin, S. V.; Fenton, E. E.; Wilson, S. R.; Loweth, C. J.; Zimmerman, S. C. Angew. Chem., Int. Ed. Engl. 1996, 34, 4, 2654-2657.
10. (h) Aoyama, Y.; Endo, Y.; Anzai, T.; Yamaguchi, Y.; Tomoya, S.; Kobayashi, K.; Kanehisa, N.; Hashimoto, H.; Kai, Y.; Masuda, H. J. Am. Chem. Soc. 1996, 118, 5562-5571.
11. (i) Hollingsworth, M. D.; Brown, M. E.; Hillier, A. C.; Santasiero, B. D.; Chaney, J. D. Science 1996, 273, 1355-1359.
12. (j) Ramamurthy, V.; Eaton, D. Chem. Mater. 1994, 6, 1128-1136.
13. (k) Herbstein, F. H. Compr. Supramol. Chem. 1996, 6, 61-83.
14. Aäkeroy, C. B.; Nieuwenhuyzen, M. J. Mol. Struct. 1996, 374, 223-239.
15. Ermer, O.; Lindenberg, L. Helv. Chim. Acta 1991, 74, 825-877.
16. Ung, A. T.; Bishop, R.; Craig, D. C.; Dance, I. G.; Scudder, M. L. Tetrahedron Lett. 1993, 49, 639-648.
17. (a) Sada, K.; Kondo, T.; Yasuda, Y.; Miyata, M.; Miki, K. Chem. Lett. 1994, 727-730.
18. (b) Hennigar, T. L.; MacQuarrie, D. C.; Losier, P.; Rogers, R. D.; Zaworotko, M. J. Angew. Chem., Int. Ed. Engl. 1997, 36, 972-973.
19. (a) Russell, V. A.; Ward, M. D. Chem. Mater. 1996, 8, 1654-1666.
20. (b) Russell, V. A.; Etter, M. C.; Ward, M. D. J. Am. Chem. Soc. 1994, 116, 1941-1952.
21. (c) Russell, V. A.; Etter, M. C.; Ward, M. D. Chem. Mater. 1994, 6, 1206-1217.
22. (d) Russell, V. A.; Ward, M. D. J. Mater. Chem. 1997, 7, 1123-1133.
23. (a) Russell, V. A.; Evans, C. C.; Li, W.; Ward, M. D. Science 1997, 276, 575-579.
24. (b) Swift, J. A.; Russell, V. A.; Ward, M. D. Adv. Mater. 1997, 9, 1183-1186.
25. Ermer, O. J. Am. Chem. Soc. 1988, 110, 3747-3754.
26. Simard, M.; Su. D.; Wuest, J. D. J. Am. Chem. Soc. 1991, 113, 4696-4698.
27. Copp, S. B.; Subramanian, S.; Zaworotko, M. J. J. Am. Chem. Soc. 1992, 114, 8719-8720.
28. Reddy, D. S.; Craig, D. C.; Rae, A. D.; Desiraju, G. R. J. Chem. Soc., Chem. Commun. 1993, 1737-1739.
29. Batten, S. R.; Hoskins, B. F.; Robson, R. J. Am. Chem. Soc. 1995, 117, 5385-5386.
30. Swift, J. A.; Reynolds, A. M.; Ward, M. D. Chem. Mater., in press.
31. Swift, J. A.; Pivovar, A. M.; Reynolds, A. M. J. Am. Chem. Soc. 1998, 120, 5887-5894.
32. 001 reflections.
33. Brown, C. J. Acta Crystallogr. 1966, 21, 146-152.
34. 2(BPDS) bilayer is defined by the distance between two opposing GS sheets in which the G ions and S oxygen atoms are coplanar, using the van der Waals radii of the guanidinium carbon atoms.
35. Bondi, A. J. Phys. Chem. 1964, 68, 441-451.
36. 2(ABDS)·DVB, respectively.
37. Blessing, R. Acta Crystallogr. 1995, A51, 33-38.
38. Clarke, H. T. J. Org. Chem. 1971, 36, 3816-3819.
39. Spek, A. L. Acta Crystallogr. 1990, A46, C34.