Resorcin[4]arene dimer linked by eight water molecules and incorporating a tetraethylammonium ion: guest-driven capsule formation via cation–π interactions

Abstract

X-Ray analysis of the co-crystallization compound formed between tetraethylresorcin[4]arene 1 and tetraethylammonium ion, Et₄N⁺·1·1^–·8H₂O·2EtOH, has shown that the two ‘head-to-head’ arranged resorcinarenes are linked by eight water molecules and encapsulate a tetraethylammonium ion within the cavity via cation–π interactions.

References

1. D. J. Cram and J. M. Cram, Container Molecules and Their Guests, The Royal Society of Chemistry, Cambridge, UK, 1994; R. C. Helgeson, C. B. Knobler and D. J. Cram, J. Am. Chem. Soc., 1997, 119, 3229 and references cited therein.
2. B.-H. Huisman, D. M. Rudkevich, F. C. J. M. van Veggel and D. N. Reinhoudt, J. Am. Chem. Soc., 1996, 118, 3523 and references cited therein.
3. A. Collet, Cryptophanes, in Comprehensive Supramolecular Chemisry, ed. F. Vögtle, Pergamon, 1996, vol. 2, ch. 11, pp. 325–365.
4. Y.-M. Jeon, J. Kim, D. Whang and K. Kim, J. Am. Chem. Soc., 1996, 118, 9790.
5. R. Wyler, J. de Mendoza and J. Rebek, Jr., Angew. Chem., Int. Ed. Engl., 1993, 32, 1699; J. Kang and J. Rebek, Jr., Nature, 1997, 385, 50 and references cited therein.
6. K. D. Shimizu and J. Rebek, Jr., Proc. Natl. Acad. Sci. USA, 1995, 92, 12 403; R. K. Castellano, D. M. Rudkevich and J. Rebek, Jr., J. Am. Chem. Soc., 1996, 118, 10 002 and references cited therein O. Mogck, M. Pons, V. Böhmer and W. Vogt, J. Am. Chem. Soc., 1997, 119, 5706 and references cited therein.
7. R. G. Chapman and J. C. Sherman, J. Am. Chem. Soc., 1995, 117, 9081; K. Nakamura, C. Sheu, A. E. Keating, K. N. Houk, J. C. Sherman, R. G. Chapman and W. L. Jorgensen, J. Am. Chem. Soc., 1997, 119, 4321.
8. L. R. MacGillivray and J. L. Atwood, Nature, 1997, 389, 469.
9. D. A. Dougherty, Science, 1996, 271, 163.
10. K. Murayama and K. Aoki, Chem. Commun., 1997, 119 and references cited therein.
11. K. Murayama and K. Aoki, unpublished results.
12. L. M. Tunstad, J. A. Tucker, E. Dalcanale, J. Weiser, J. A. Bryant, J. C. Sherman, R. C. Helgeson, C. B. Knobler and D. J. Cram, J. Org. Chem., 1989, 54, 1306.
13. G. Mann, L. Hennig, F. Weinelt, K. Müller, R. Meusinger, G. Zahn and T. Lippmann, Supramol. Chem., 1994, 3, 101.
14. F. Davis and C. J. M. Stirling, J. Am. Chem. Soc., 1995, 117, 10 385.
15. L. R. MacGillivray and J. L. Atwood, J. Am. Chem. Soc., 1997, 119, 6931.
16. Z. Lin and M. E. Johnson, FEBS Lett., 1995, 370, 1; D. Barak, A. Ordentlich, Y. Segall, B. Velan, H. P. Benshop, L. P. A. D. Jong and A. Schafferman, J. Am. Chem. Soc., 1997, 119, 3157.
17. Y. Aoyama, Y. Tanaka and S. Sugahara, J. Am. Chem. Soc., 1989, 111, 5397.
18. H.-J. Schneider, D. Güttes and U. Schneider, J. Am. Chem. Soc., 1988, 110, 6449.