Copper(II) Complexes of N,N'-Bis((2-substituted-imidazol-4-yl)methylene)-3,3′-diaminodi- propylamine (2-Substituent = H, Me): Δ and Δ Enantiomorphs of the Protonated Complex and Helical Structure of the Deprotonated Complex Formed by Hydrogen Bonds

Inorganic Chemistry

Volumn 36, Issue 20, 1997, Pages 4329-4335

  Miyasaka, Hitoshi ^a   Okamura, Shingo ^a   Nakashima, Toshio ^b   Matsumoto, Naohide ^c  

^a KYUSHU UNIVERSITY   (Japan)

^b OITA UNIVERSITY   (Japan)

^c KUMAMOTO UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0000081901     PISSN: 00201669     EISSN: None     Source Type: Journal    
DOI: 10.1021/ic970425v     Document Type: Article

References (41)

1. (a) Lehn, J.-M. Supramolecular Chemistry; VCH: Weinheim, Germany, 1995.
2. (b) Lehn, J.-M. Angew. Chem., Int. Ed. Engl. 1990, 29, 1304.
3. Transition Metals in Supramolecular Chemistry; Fabbrizzi, L., Poggi, A., Eds.; ASI Kluwer Academic Publishers: Dordrecht, The Netherlands, 1994.
4. Vogtle, F. Supramolecular Chemistry; Wiley: New York, 1991.
5. See for examples: (a) Abrahams, B. F.; Hoskins, B. F.; Michail, D. M.; Robson, R. Nature 1994, 369, 727. (b) Fujita, M.; Kwon, Y. J.; Sasaki, O.; Yamaguchi, K.; Ogura, K. J. Am. Chem. Soc. 1995, 117, 7287. Kawata, S.; Kitagawa, S.; Kumagai, H.; Kudo, C.; Kamesaki, H.; Ishiyama, T.; Suzuki, R.; Kondo, M.; Katada, M. Inorg. Chem. 1996, 35, 4449. Yaghi, O. M.; Li, G.: Li, H. Nature 1995, 378, 703. (e) Carlucci, L.; Ciani, G.; Proserpio, D. M.; Sironi, A. J. Am. Chem. Soc. 1995, 117, 4562.
6. See for examples: (a) Abrahams, B. F.; Hoskins, B. F.; Michail, D. M.; Robson, R. Nature 1994, 369, 727. (b) Fujita, M.; Kwon, Y. J.; Sasaki, O.; Yamaguchi, K.; Ogura, K. J. Am. Chem. Soc. 1995, 117, 7287. Kawata, S.; Kitagawa, S.; Kumagai, H.; Kudo, C.; Kamesaki, H.; Ishiyama, T.; Suzuki, R.; Kondo, M.; Katada, M. Inorg. Chem. 1996, 35, 4449. Yaghi, O. M.; Li, G.: Li, H. Nature 1995, 378, 703. (e) Carlucci, L.; Ciani, G.; Proserpio, D. M.; Sironi, A. J. Am. Chem. Soc. 1995, 117, 4562.
7. See for examples: (a) Abrahams, B. F.; Hoskins, B. F.; Michail, D. M.; Robson, R. Nature 1994, 369, 727. (b) Fujita, M.; Kwon, Y. J.; Sasaki, O.; Yamaguchi, K.; Ogura, K. J. Am. Chem. Soc. 1995, 117, 7287. Kawata, S.; Kitagawa, S.; Kumagai, H.; Kudo, C.; Kamesaki, H.; Ishiyama, T.; Suzuki, R.; Kondo, M.; Katada, M. Inorg. Chem. 1996, 35, 4449. Yaghi, O. M.; Li, G.: Li, H. Nature 1995, 378, 703. (e) Carlucci, L.; Ciani, G.; Proserpio, D. M.; Sironi, A. J. Am. Chem. Soc. 1995, 117, 4562.
8. See for examples: (a) Abrahams, B. F.; Hoskins, B. F.; Michail, D. M.; Robson, R. Nature 1994, 369, 727. (b) Fujita, M.; Kwon, Y. J.; Sasaki, O.; Yamaguchi, K.; Ogura, K. J. Am. Chem. Soc. 1995, 117, 7287. Kawata, S.; Kitagawa, S.; Kumagai, H.; Kudo, C.; Kamesaki, H.; Ishiyama, T.; Suzuki, R.; Kondo, M.; Katada, M. Inorg. Chem. 1996, 35, 4449. Yaghi, O. M.; Li, G.: Li, H. Nature 1995, 378, 703. (e) Carlucci, L.; Ciani, G.; Proserpio, D. M.; Sironi, A. J. Am. Chem. Soc. 1995, 117, 4562.
9. See for examples: (a) Abrahams, B. F.; Hoskins, B. F.; Michail, D. M.; Robson, R. Nature 1994, 369, 727. (b) Fujita, M.; Kwon, Y. J.; Sasaki, O.; Yamaguchi, K.; Ogura, K. J. Am. Chem. Soc. 1995, 117, 7287. Kawata, S.; Kitagawa, S.; Kumagai, H.; Kudo, C.; Kamesaki, H.; Ishiyama, T.; Suzuki, R.; Kondo, M.; Katada, M. Inorg. Chem. 1996, 35, 4449. Yaghi, O. M.; Li, G.: Li, H. Nature 1995, 378, 703. (e) Carlucci, L.; Ciani, G.; Proserpio, D. M.; Sironi, A. J. Am. Chem. Soc. 1995, 117, 4562.
10. See for examples: (a) Constable, E. C. Tetrahedron 1992, 48, 10013. (b) Potts, K. T.; Keshavarz-K, M.; Tham, F. S.; Abruña, H. D.; Arana, C. Inorg. Chem. 1993, 32, 4436. Krämer, R.; Lehn, J.-M.; Cian, A. D.; Fischer, J. Angew. Chem., Int. Ed. Engl. 1993, 32, 703. Gelling, O. J.: Bolhuis, F. v.; Feringa, B. L. J. Chem. Soc., Chem. Commun. 1991, 917.
11. See for examples: (a) Constable, E. C. Tetrahedron 1992, 48, 10013. (b) Potts, K. T.; Keshavarz-K, M.; Tham, F. S.; Abruña, H. D.; Arana, C. Inorg. Chem. 1993, 32, 4436. Krämer, R.; Lehn, J.-M.; Cian, A. D.; Fischer, J. Angew. Chem., Int. Ed. Engl. 1993, 32, 703. Gelling, O. J.: Bolhuis, F. v.; Feringa, B. L. J. Chem. Soc., Chem. Commun. 1991, 917.
12. See for examples: (a) Constable, E. C. Tetrahedron 1992, 48, 10013. (b) Potts, K. T.; Keshavarz-K, M.; Tham, F. S.; Abruña, H. D.; Arana, C. Inorg. Chem. 1993, 32, 4436. Krämer, R.; Lehn, J.-M.; Cian, A. D.; Fischer, J. Angew. Chem., Int. Ed. Engl. 1993, 32, 703. Gelling, O. J.: Bolhuis, F. v.; Feringa, B. L. J. Chem. Soc., Chem. Commun. 1991, 917.
13. See for examples: (a) Constable, E. C. Tetrahedron 1992, 48, 10013. (b) Potts, K. T.; Keshavarz-K, M.; Tham, F. S.; Abruña, H. D.; Arana, C. Inorg. Chem. 1993, 32, 4436. Krämer, R.; Lehn, J.-M.; Cian, A. D.; Fischer, J. Angew. Chem., Int. Ed. Engl. 1993, 32, 703. Gelling, O. J.: Bolhuis, F. v.; Feringa, B. L. J. Chem. Soc., Chem. Commun. 1991, 917.
14. (a) Tamaki, H.; Zhong, Z. J.; Matsumoto, N.; Kida, S.; Koikawa, M.; Achiwa, N.; Hashimoto, Y.; Okawa, H. J. Am. Chem. Soc. 1992, 114, 6974.
15. (b) Stumpf, H.; Ouahab, L.; Pei, Y.; Grandjean, D.; Kahn, O. Science 1993, 261, 447.
16. Ohba, M.; Okawa, H.; Fukita, N.; Hashimoto, Y. J. Am. Chem. Soc. 1997, 119, 1011.
17. Miyasaka, H.; Matsumoto, N.; Okawa, H.; Re, N.; Gallo, E.; Floriani, C. J. Am. Chem. Soc. 1996, 118, 981.
18. (e) Re, N.; Gallo, E.; Floriani, C.; Miyasaka, H.; Matsumoto, N. Inorg. Chem. 1996, 35, 6004.
19. (f) Miyasaka, H.; Matsumoto, N.; Re, N.; Gallo, E.; Floriani, C. Inorg. Chem. 1997, 36, 670.
20. Lehn, J.-M. Supramolecular Chemistry, VCH: Weinheim, Germany, 1995; Section 8-5.
21. (a) Matsumoto, N.; Yamashita, S.; Ohyoshi, A.; Kohata, S.; Okawa, H. J. Chem. Soc., Dalton Trans. 1988, 1943.
22. (b) Matsumoto, N.; Akui, T.; Murakami, H.; Kanesaka, J.; Ohyoshi, A.; Okawa, H. J. Chem. Soc., Dalton Trans. 1988, 1021.
23. Matsumoto, N.; Tamaki, H.; Inoue, K.; Koikawa, M.; Maeda, Y.; Okawa, H.; Kida, S. Chem. Lett. 1991, 1393.
24. Matsumoto, N.; Nozaki, T.; Ushio, H.; Motoda, K.; Ohba, M.; Mago, G.; Okawa, H. J. Chem. Soc., Dalton Trans. 1993, 2157.
25. (e) Nozaki, T.; Ushio, H.; Mago, G.; Matsumoto, N.; Okawa, H.; Yamakawa, Y.; Anno, T.; Nakashima, T. J. Chem. Soc., Dalton Trans. 1994, 2339.
26. (f) Matsumoto, N.; Mizuguchi, Y.; Mago, G.; Eguchi, S.; Miyasaka, H.; Nakashima, T.; Tuchagues, J. P. Angew. Chem., Int. Ed. Engl., in press.
27. Gran, G. Analyst 1952, 77, 661.
28. Beck, M. T.; Nagypal, I. In Chemistry of Complex Equilibria; Wiley: New York, 1990; p 44.
29. Sheldrick, G. M. SHELXS86, A program for X-ray crystal structure determination, University of Cambridge, 1986.
30. Beurskens, P. T.; Admiraal, G.; Beurskens, G.; Bosman, W. P.; Garcia-Granda, S.; Gould, R. O.; Smits, J. M. M.; Smykalla, C. DIRDIF92. The DIRDIF program system, Technical Report of the Crystallography Laboratory, University of Nijmegen, The Netherlands, 1992.
31. Creagh, D. C.; McAuley, W. J. International Tables for Crystallography; Wilson, A. J. C., Ed.; Kluwer Academic Publishers: Boston, MA, 1992; Vol C, Table 4 pp 219-222. Cromer, D. T.; Waber, J. T. International Tables for X-ray Crystallography; The Kynoch Press: Birmingham, England, 1974; Vol. IV, Table 2.2A.
32. Creagh, D. C.; McAuley, W. J. International Tables for Crystallography; Wilson, A. J. C., Ed.; Kluwer Academic Publishers: Boston, MA, 1992; Vol C, Table 4 pp 219-222. Cromer, D. T.; Waber, J. T. International Tables for X-ray Crystallography; The Kynoch Press: Birmingham, England, 1974; Vol. IV, Table 2.2A.
33. Creagh, D. C.; Hubbel, J. H. International Tables for Crystallography; Wilson, A. J. C. Ed.; Kluwer Academic Publishers: Boston, MA, 1992; Vol. C, Table 4.2.4.3, pp 200-206. Creagh, D. C.; McAuley, W. J. International Tables for Crystallography; Wilson, A. J. C., Ed.; Kluwer Academic Publishers: Boston, MA, 1992; Vol. C, Table 4.2.6.8, pp 219-222.
34. Creagh, D. C.; Hubbel, J. H. International Tables for Crystallography; Wilson, A. J. C. Ed.; Kluwer Academic Publishers: Boston, MA, 1992; Vol. C, Table 4.2.4.3, pp 200-206. Creagh, D. C.; McAuley, W. J. International Tables for Crystallography; Wilson, A. J. C., Ed.; Kluwer Academic Publishers: Boston, MA, 1992; Vol. C, Table 4.2.6.8, pp 219-222.
35. teXsan: Crystal Structure Analysis Package, Molecular Structure Corp., 1985, 1992.
36. Addison, A. W.; Rao, T. N.; Reedijk, J.; van Rijn, J.; Verschoor, G. C. J. Chem. Soc., Dalton Trans. 1984, 1349.
37. Nomenclature of Inorganic Chemistry, Recommendations 1990; Blackwell: Oxford, U.K., 1990.
38. In ref 15, the symbol of chirality used for these complexes is C (clockwise) and A (anticlockwise) instead of Δ and Δ. In this paper, the symbols of Δ and Δ are used to describe the chirality for the reported complexes, because of the identical chirality for the parental complex and the produced helical chain.
39. (a) Jacques, J.; Collet, A.; Wilen, S. H. Enantiomers, Racemates and Resolutions; Kringer: Malabar, FL, 1991.
40. (b) Cray, D. P.; Mellor, D. P. Top. Curr, Chem. 1976, 63, 1.
41. Lehn, J.-M. Supramolecular Chemistry; VCH: Weinheim, Germany, 1995; Section 9.7.