Two-dimensional hexagonal hydrogen-bonded network with triangle-like large cavities: Hexakis(4-carboxyphenyl)benzene

Tetrahedron Letters

Volumn 41, Issue 1, 2000, Pages 89-93

  Kobayashi, Kenji ^a   Shirasaka, Toshiaki ^a   Horn, Ernst ^a,b   Furukawa, Naomichi ^a  

^a UNIVERSITY OF TSUKUBA   (Japan)

^b RIKKYO UNIVERSITY   (Japan)

Author keywords

Carboxylic acid derivatives; Carboxylic acids; Hydrogen bonding; Supramolecular chemistry; X ray crystallography

Indexed keywords

ACETYLENE DERIVATIVE; BENZENE DERIVATIVE; CARBOXYLIC ACID; CARBOXYLIC ACID DERIVATIVE;

ARTICLE; CATALYSIS; CHEMICAL MODIFICATION; CRYSTAL STRUCTURE; HYDROGEN BOND; SYNTHESIS; X RAY CRYSTALLOGRAPHY;

EID: 0033992429     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(99)02008-0     Document Type: Article

References (26)

1. (a) Russell, V. A.; Evans, C. C.; Li, W.; Ward, M. D. Science 1997, 276, 575.
2. (b) Janiak, C. Angew. Chem., Int. Ed. Engl. 1997, 36, 1431.
3. (c) Brunet, P.; Simard, M.; Wuest, J. D. J. Am. Chem. Soc. 1997, 119, 2737.
4. (d) Yaghi, O. M.; Li, H.; Davis, C.; Richardson, D.; Groy, T. L. Acc. Chem. Res. 1998, 31, 474.
5. (e) Dewa, T.; Endo, K.; Aoyama, Y. J. Am. Chem. Soc. 1998, 120, 8933.
6. (f) Kondo, M.; Okubo, T.; Asami, A.; Noro, S.; Yoshitomi, T.; Kitagawa, S.; Ishii, T.; Matsuzaka, H.; Seki, K. Angew. Chem., Int. Ed. 1999, 38, 140.
7. (a) Fujita, M.; Kwon, Y. J.; Washizu, S.; Ogura, K. J. Am. Chem. Soc. 1994, 116, 1151.
8. (b) Endo, K.; Koike, T.; Sawaki, T.; Hayashida, O.; Masuda, H.; Aoyama, Y. J. Am. Chem. Soc. 1997, 119, 4117.
9. (c) Sawaki, T.; Aoyama, Y. J. Am. Chem. Soc. 1999, 121, 4793.
10. (a) Duchamp, D. J.; Marsh, R. E. Acta Crystallogr. Sect. B 1969, 25, 5.
11. (b) Ermer, O. J. Am. Chem. Soc. 1988, 110, 3747.
12. (c) Batten, S. R.; Robson, R. Angew. Chem., Int. Ed. 1998, 37, 1460.
13. Venkataraman, D.; Lee, S.; Zhang, J.; Moore, J. S. Nature 1994, 371, 591.
14. (a) Kobayashi, K.; Endo, K.; Aoyama, Y.; Masuda, H. Tetrahedron Lett. 1993, 34, 7929.
15. (b) Endo, K.; Sawaki, T.; Koyanagi, M.; Kobayashi, K.; Masuda, H.; Aoyama, Y. J. Am. Chem. Soc. 1995, 117, 8341.
16. (c) Kobayashi, K.; Koyanagi, M.; Endo, K.; Masuda, H.; Aoyama, Y. Chem. Eur. J. 1998, 4, 417.
17. Kobayashi, K.; Shirasaka, T.; Sato, A.; Horn, E.; Furukawa, N. Angew. Chem., Int. Ed. 1999, in press.
18. Hexagonal networks via CH-N and CH-O interactions are known for the crystal structures of 1,3,5-tricyanobenzene and trimethylisocyanurate, respectively. These networks, however, do not have enough cavities to accommodate guest molecules. (a) Reddy, D. S.; Goud, B. S.; Panneerselvam, K.; Desiraju, G. R. J. Chem. Soc., Chem. Commun. 1993, 663.
19. (b) Thalladi, V. R.; Panneerselvam, K.; Carrell, C. J.; Carrell, H. L.; Desiraju, G. R. J. Chem. Soc., Chem. Commun. 1995, 341.
20. Recent examples on two-dimensional hydrogen-bonded networks using carboxylic acid groups: (a) Kolotuchin, S. V.; Fenlon, E. E.; Wilson, S. R.; Loweth, C. J.; Zimmerman, S. C. Angew. Chem., Int. Ed. Engl. 1995, 34, 2654.
21. (b) Holy, P.; Závada, J.; Císarová, I.; Podlaha, J. Angew. Chem., Int. Ed. 1999, 38, 381.
22. 2O: C, 70.59; H, 3.95. Found: C, 70.84; H, 4.05.
23. w=0.043, and GOF=1.26 using 3492 unique reflections (I>3.0σ(I)).
24. Crystal structure of 1·4(MeOH) has not been solved because of its instability due to quick loss of MeOH.
25. (a) Diederich, F. Nature 1994, 369, 199.
26. (b) Haley, M. M. Synlett 1998, 557.