Crystalline inclusion compounds of 1-(9-anthryloxy)anthraquinone as a host compound: X-ray structural characterization and π-π interaction modes in the crystal enclathrating benzene as a guest

Journal of the Chemical Society. Perkin Transactions 2

Volumn 6, Issue , 1996, Pages 1139-1145

  Ochiai, Kazunori ^a   Mazaki, Yasuhiro ^a   Nishikiori, Shin Ichi ^a   Kobayashi, Keiji ^a   Hayashi, Shigenobu ^b  

^a UNIVERSITY OF TOKYO   (Japan)

^b NATL INST OF MAT AND CHEM RES   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0001019356     PISSN: 03009580     EISSN: None     Source Type: Journal    
DOI: 10.1039/P29960001139     Document Type: Article

References (47)

1. (a) E. Weber and M. Czugler, in Molecular Inclusion and Molecular Recognition-Clathrates I and II, ed. E. Weber, in Top. Curr. Chem., Springer-Verlag Berlin, 1988, vol. 149, p. 45;
2. (b) E. Weber, in Inclusion Phenomena and Molecular Recognition, ed. J. L. Atwood, Plenum Press, New York, 1990, vol. 4, p. 188.
3. J-M. Lehn, Angew. Chem., Int. Ed. Engl., 1990, 29, 1304;
4. (b) J. Rebek, Jr., Angew. Chem., Int. Ed. Engl., 1990, 29, 245;
5. (c) J. C. MacDonald and G. M. Whitesides, Chem. Rev., 1994, 94, 2383;
6. (d) G. Kaupp, Angew. Chem., Int. Ed., Engl., 1994, 33, 728;
7. (e) F. Toda, K. Tanaka, Z. Stein and I. Goldberg, J. Org. Chem., 1994, 59, 5748 and refs. cited therein.
8. For crystal engineering, see: G. R. Desiraju, Crystal Engineering, Elsevier, Amsterdam, 1989.
9. For dynamic, behaviours of guest molecules, see recent examples: (a) K. D. M. Harris, Chem. Britain, 1993, 132;
10. (b) A. Mahdyarfar and K. D. M. Harris, J. Chem. Soc., Chem. Commun., 1993, 51;
11. (c) M. D. Hollingsworth, J. Am. Chem. Soc., 1993, 115, 5881;
12. (d) A. E. Aliev and K. D. M. Harris, J. Am. Chem. Soc:, 1993, 115, 6369;
13. (e) F. Toda et al., J. Chem. Soc., Chem. Commun., 1993, 1139;
14. (f) M. D. Hollingsworth, B. D. Santarsiero and K. O. M. Harris, Angew. Chem., Int. Ed. Engl., 1994, 33, 649;
15. (g) F. Imashiro, J. Am. Chem. Soc., 1993, 115, 2231;
16. (h) M. E. Brown and M. D. Hollingsworth, Nature, 1995, 376, 323.
17. For reactions in clathrate crystals, see: N. Hayashi, Y. Mazaki and K. Kobayashi, Tetrahedron Lett., 1994, 35, 5883.
18. For a recent non-ionic three-component complex, see: L. J. Barbour, J. W. Steed and J. L. Atwood, J. Chem. Soc., Perkin Trans. 2, 1995, 857.
19. K. Ochiai, Y. Mazaki and K. Kobayashi, Tetrahedron Lett., 1995, 36, 5947.
20. (a) F. Toda, Molecular Inclusion and Molecular Recognition-Clathrates I, in Top. Curr. Chem., vol. 140, Springer-Verlag, Berlin, Heidelberg, 1987, p. 43;
21. (b) F. Toda, Molecular Inclusion and Molecular Recognition-Clathrates II in Top. Curr. Chem., vol. 149, Springer-Verlag, Berlin, Heidelberg, 1988, p. 211.
22. (a) Y. Mazaki, N. Hayashi and K. Kobayashi, J. Chem. Soc., Chem. Commun., 1992, 1381;
23. (b) Y. Mazaki, K. Awaga and K. Kobayashi, J. Chem. Soc., Chem. Commun., 1992, 1661;
24. (c) N. Hayashi, Y. Mazaki and K. Kobayashi, Adv. Mater., 1994, 6, 654;
25. (d) N. Hayashi, Y. Mazaki and K. Kobayashi, J. Org. Chem., 1995, 60, 6342.
26. N. Hayashi, Y. Mazaki and K. Kobayashi, J. Chem. Soc., Chem. Commun., 1994, 2351.
27. (a) C. A. Hunter, Chem. Soc. Rev., 1994, 101;
28. (b) C. A. Hunter, Angew. Chem., Int. Ed. Engl., 1993, 32, 1584;
29. (c) P. Hobza, H. L. Sezle and E. W. Schlag, J. Am. Chem. Soc., 1994, 116, 3500.
30. For edge-to-face aromatic interactions, see: M. C. Grossel, A. K. Cheetham, D. A. O. Hope and S. C. Weston, J. Org. Chem, 1993, 58, 6654, and refs. cited therein.
31. M. Nishio, Y. Umezawa, M. Hirota and Y. Takeuchi, Tetrahedron, 1995, 51, 8665.
32. C. A. Hunter, R. H. Haueisen and A. Irving, Angew. Chem., Int. Ed. Engl., 1994, 33, 566.
33. T. E. Muller, D. M. P. Mingos and D. J. Williams, J. Chem. Soc., Chem. Commun., 1994, 1787.
34. M. Etter, Acc. Chem. Res., 1990, 23, 120.
35. L. R. Hanton, C. A. Hunter and D. H. Purvis, J. Chem. Soc., Chem. Commun., 1992, 1134.
36. (a) A. E. Aliev, S. P. Smart and K. D. Harris. J. Mater. Chem., 1994, 4, 35;
37. (b) N. J. Heaton, R. L. Vold and R. R. Vold, J. Am. Chem. Soc., 1989, 111, 3211;
38. (c) E. Meirovitch and I. Belsky, J. Phys. Chem., 1984, 88, 6407;
39. (d) M. Meirovitch, T. Krant and S. Vega, J. Phys. Chem., 1983, 87, 1390.
40. J. H. Ok, R. R. Vold, R. L. Vold and M. C. Etter, J. Phys. Chem., 1989, 93, 7618.
41. (a) M. D. Cohen, Angew. Chem., Int. Ed. Engl., 1975, 14, 386;
42. (b) V. Ramamurthy and K. Venkatesan, Chem. Rev., 1987, 87, 433.
43. (a) Y. Ohashi, A. Uchida, Y. Sasada and Y. Ohgo, Acta Crystallogr., Sect. B, 1983, 39, 54;
44. (b) Reactivity in Molecular Crystals, Y. Ohashi, ed. VCH-Kodansha, 1993;
45. (c) Y. Ohashi, K. Yanagi, T. Kurihara, Y. Sasada and Y. Ogo, J. Am. Chem. Soc., 1981, 103, 5805.
46. L. Echegoyen, Y. Hafez, R. C. Lawson, J. de Mendoza and T. Torres, J. Org. Chem., 1993, 58, 2009.
47. J. Vega and Z. Luz, J. Chem. Phys., 86, 1987, 86, 1803.