Supramolecular chirality in layered crystals of achiral ammonium salts and fatty acids: A hierarchical interpretation

Angewandte Chemie - International Edition

Volumn 45, Issue 25, 2006, Pages 4142-4145

  Tanaka, Akira ^a   Inoue, Katsunari ^a   Hisaki, Ichiro ^a   Tohnai, Norimitsu ^a   Miyata, Mikiji ^a   Matsumoto, Akikazu ^b  

^a OSAKA UNIVERSITY   (Japan)

^b Osaka Prefecture University   (Japan)

Author keywords

Chirality; Crystal engineering; Hydrogen bonds; Layered compounds; Supramolecular chemistry

Indexed keywords

ACHIRAL 4-METHYLBENZYLAMMONIUM MYRISTATE; PENTADECANOATE; SUPRAMOLECULAR CHIRALITY;

AMMONIUM COMPOUNDS; CONFORMATIONS; CRYSTAL STRUCTURE; FATTY ACIDS;

SUPRAMOLECULAR CHEMISTRY;

FATTY ACID; QUATERNARY AMMONIUM DERIVATIVE;

ARTICLE; CHEMICAL MODEL; CHEMICAL STRUCTURE; CHEMISTRY; X RAY CRYSTALLOGRAPHY;

CRYSTALLOGRAPHY, X-RAY; FATTY ACIDS; MODELS, CHEMICAL; MOLECULAR STRUCTURE; QUATERNARY AMMONIUM COMPOUNDS;

EID: 33746290534     PISSN: 14337851     EISSN: None     Source Type: Journal    
DOI: 10.1002/anie.200504424     Document Type: Article

References (32)

1. a) T. Suzuki, T. Fukushima, Y. Yamashita, T. Miyashi, J. Am. Chem. Soc. 1994, 116, 2793-2803;
2. b) H. Irngartinger, P. W. Fettel, V. Siemund, Eur. J. Org. Chem. 1998, 2079-2082;
3. c) S. Kohmoto, Y. Ono, H. Masu, K. Yamaguchi, K. Kishikawa, M. Yamamoto, Org. Lett. 2001, 3, 4153-4155;
4. d) M. Sakamoto, S. Kobaru, T. Mino, T. Fujita, Chem. Commun. 2004, 1002-1003;
5. e) H. Koshima, H. Kawanishi, M. Nagano, H. Yu, M. Shiro, T. Hosoya, H. Uekusa, Y. Ohashi, J. Org. Chem. 2005, 70, 4490-4497.
6. a) B. S. Green, M. Lahav, D. Ravinovich, Acc. Chem. Res. 1979, 12, 191-197;
7. b) A. Sekine, K. Hori, Y. Ohashi, M. Yagi, F. Toda, J. Am. Chem. Soc. 1989, 111, 697-699;
8. c) G. Kaupp, M. Haak, Angew. Chem. 1993, 105, 727-728;
9. Angew. Chem. Int. Ed. Engl. 1993, 32, 694-695.
10. a) I. Azumaya, D. Uchida, T. Kato, A. Yokoyama, A. Tanatani, H. Takayanagi, T. Yokozawa, Angew. Chem. 2004, 116, 1384-1387;
11. Angew. Chem. Int. Ed. 2004, 43, 1360-1363;
12. b) H. Koshima, S. Honke, J. Fujita, J. Org. Chem. 1999, 64, 3916-3921;
13. c) S. Jayanty, T. P. Radhakrishnan, Chem. Eur. J. 2004, 10, 2661-2667;
14. d) H. Koshima, M. Nagano, T. Asahi, J. Am. Chem. Soc. 2005, 127, 2455-2463.
15. B. Gong, C. Zheng, H. Zeng, J. Zhu, J. Am. Chem. Soc. 1999, 121, 9766-9767.
16. a) L. P. García, D. B. Amabilino, Chem. Soc. Rev. 2002, 31, 342-356;
17. b) S. Ferlay, O. Felix, M. W. Hosseini, J. M. Planeix, N. Kyritsakas, Chem. Commun. 2002, 702-703;
18. c) M. A. M. Timoneda, M. C. Calama, D. N. Reinhoudt, Chem. Soc. Rev. 2004, 33, 363-372;
19. d) X. Huang, C. Li, S. Jiang, X. Wang, B. Zhang, M. Liu, J. Am. Chem. Soc. 2004, 126, 1322-1323.
20. a) K. Sada, K. Inoue, T. Tanaka, A. Tanaka, A. Epergyes, S. Nagahama, A. Matsumoto, M. Miyata, J. Am. Chem. Soc. 2004, 126, 1764-1771;
21. b) K. Sada, K. Inoue, T. Tanaka, A. Epergyes, A. Tanaka, N. Tohnai, A. Matsumoto, M. Miyata, Angew. Chem. 2005, 117, 7221-7224;
22. Angew. Chem. Int. Ed. 2005, 44, 7059-7062.
23. Only three examples were found in a search of the Cambridge Structural Database, although the authors do not refer to chirality; see: a) V. Ketmann, E. Kello, V. Vrabel, J. Garaj, M. Karvas, M. Goghova, J. Durmis, Acta Crystallogr. Sect. C 1989, 45, 787-791;
24. b) V. B. Gaillard, W. Paciorek, K. Schenk, G. Chapuis, Acta Crystallogr. Sect. B 1996, 52, 1036-1047;
25. c) D. Braga, L. Maini, G. Sanctis, K. Rubini, F. Grepioni, M. R. Chierotti, R. Gobetto, Chem. Eur. J. 2003, 9, 5538-5548.
26. int = 0.073) and were used in all calculations. The final R1 and wR2 values were 0.077 (observed data) and 0.209 (observed data), respectively.
27. int = 0.031) and were used in all calculations. The final R1 and wR2 values were 0.046 (observed data) and 0.111 (observed data), respectively. CCDC-286085 (1-2) and -286086 (1.3) contain the supplementary crystallographic data for this paper. These data can be obtained free of charge from The Cambridge Crystallographic Data Centre via www.ccdc.cam.ac.uk/data_request/cif.
28. Although the strict definition of chirality within the twisted molecules can be expressed as +synclinal and -synclinal according to the Klyne-Prelog method, the shortened forms are adopted here for clarity; see: W. Klyne, V. Prelog, Experientia 1960, 16, 521.
29. a) M. Miyata, K. Sada, Comprehensive Supramolecular Chemistry. Vol. 6 (Eds.: D. D. MacNicol, F. Toda, R. Bishop), Pergamon, Oxford, 1996, pp. 147-176;
30. b) K. Kato, K. Inoue, N. Tohnai, M. Miyata, J. Inclusion Phenom. Macrocycl. Chem. 2004, 48, 61-67;
31. c) "Separations and Reactions in Organic Supramolecular Chemistry": M. Miyata, N. Yoswathananont, K. Nakano, K. Sada in Perspectives in Supramolecular Chemistry, Vol. 8 (Eds.: F. Toda, R. Bishop), Wiley, New York, 2004, pp. 87-122, chap. 4;
32. d) T. Watabe, K. Kato, N. Tohnai, M. Miyata in Structure and Dynamics in Macromolecular Systems with Specific Interactions (Eds.: K. Adachi, T. Sato), Osaka University Press, 2005, pp. 157-167.