The Simultaneous Use of H-Bonding and Coulomb Interactions for the Self-Assembly of Fumaric Acid and Cyclic Bisamidine into One and Two-Dimensional Molecular Networks

Angewandte Chemie (International Edition in English)

Volumn 36, Issue 1-2, 1997, Pages 102-104

  Félix, Olivier ^a   Hosseini, Mir Wais ^a   De Cian, André ^b   Fischer, Jean ^b  

^a CNRS   (France)

^b NONE

Author keywords

Amidines; Crystal engineering; Furmiric acid; Hydrogen bonds; Supramolecular chemistry

Indexed keywords

EID: 0030812321     PISSN: 05700833     EISSN: None     Source Type: Journal    
DOI: 10.1002/anie.199701021     Document Type: Article

References (32)

1. J.-M. Lehn, Supramolecular Chemistry Concepts Perspectives, VCH, Weinheim, 1995.
2. G. R. Desiraju, Angew. Chem. 1995, 107, 2541; Angew. Chem. Int. Ed. Engl. 1995, 34, 2311; Crystallography of Supramolecular Compounds (Eds.: G. Tsoucaris, J. L. Atwood, J. Lipkowski), Kluwer, Dordrecht, Niederlande, 1996.
3. G. R. Desiraju, Angew. Chem. 1995, 107, 2541; Angew. Chem. Int. Ed. Engl. 1995, 34, 2311; Crystallography of Supramolecular Compounds (Eds.: G. Tsoucaris, J. L. Atwood, J. Lipkowski), Kluwer, Dordrecht, Niederlande, 1996.
4. G. R. Desiraju, Angew. Chem. 1995, 107, 2541; Angew. Chem. Int. Ed. Engl. 1995, 34, 2311; Crystallography of Supramolecular Compounds (Eds.: G. Tsoucaris, J. L. Atwood, J. Lipkowski), Kluwer, Dordrecht, Niederlande, 1996.
5. M. C. Etter, Acc. Chem. Res. 1990, 23, 120; G. M. Whitesides, J. P. Mathias, T. Seto, Science 1991, 254, 1312.
6. M. C. Etter, Acc. Chem. Res. 1990, 23, 120; G. M. Whitesides, J. P. Mathias, T. Seto, Science 1991, 254, 1312.
7. D. S. Lawrence, T. Jiang, M. Levett, Chem. Rev. 1995, 95, 2229; J. F. Stoddart, D. Philp. Angew. Chem. 1996, 108, 1242; Angew. Chem. Int. Ed. Engl. 1996, 35, 1154.
8. D. S. Lawrence, T. Jiang, M. Levett, Chem. Rev. 1995, 95, 2229; J. F. Stoddart, D. Philp. Angew. Chem. 1996, 108, 1242; Angew. Chem. Int. Ed. Engl. 1996, 35, 1154.
9. D. S. Lawrence, T. Jiang, M. Levett, Chem. Rev. 1995, 95, 2229; J. F. Stoddart, D. Philp. Angew. Chem. 1996, 108, 1242; Angew. Chem. Int. Ed. Engl. 1996, 35, 1154.
10. a) M. Simard, D. Su, J. D. Wuest, J. Am. Chem. Soc. 1991, 113, 4696.
11. F. Hajek, E. Graf, M. W. Hosseni, X. Delaigue, A. De Cian, J. Fischer, Tetrahedron Lett. 1996, 37, 1401.
12. C. B. Aakeröy, K. R. Seddon, Chem. Soc. Rev. 1993, 22, 397; S. Subramanian, M. J. Zaworotko, Coord. Chem. Rev. 1994, 137, 357, and references therein.
13. C. B. Aakeröy, K. R. Seddon, Chem. Soc. Rev. 1993, 22, 397; S. Subramanian, M. J. Zaworotko, Coord. Chem. Rev. 1994, 137, 357, and references therein.
14. M. D. Ward. P. J. Fagan, J. C. Calabrese, D. C. Johnson, J. Am. Chem. Soc. 1989, 111, 1719; E. Fan, J. Yang, S. J. Geib, T. C. Stoner, M. D. Hopkins, A. D. Hamilton, J. Chem. Soc. Chem. Commun. 1995, 1251; K. E. Schiebert, D. N. Chin, J. C. MacDonald, G. M. Whitesides. J. Am. Chem. Soc. 1996, 118, 4018.
15. M. D. Ward. P. J. Fagan, J. C. Calabrese, D. C. Johnson, J. Am. Chem. Soc. 1989, 111, 1719; E. Fan, J. Yang, S. J. Geib, T. C. Stoner, M. D. Hopkins, A. D. Hamilton, J. Chem. Soc. Chem. Commun. 1995, 1251; K. E. Schiebert, D. N. Chin, J. C. MacDonald, G. M. Whitesides. J. Am. Chem. Soc. 1996, 118, 4018.
16. M. D. Ward. P. J. Fagan, J. C. Calabrese, D. C. Johnson, J. Am. Chem. Soc. 1989, 111, 1719; E. Fan, J. Yang, S. J. Geib, T. C. Stoner, M. D. Hopkins, A. D. Hamilton, J. Chem. Soc. Chem. Commun. 1995, 1251; K. E. Schiebert, D. N. Chin, J. C. MacDonald, G. M. Whitesides. J. Am. Chem. Soc. 1996, 118, 4018.
17. a) G. Brand, M. W. Hosseini, R. Ruppert, A. De Cian, J. Fischer, N. Kyritsakas, New J. Chem. 1995, 19, 9;
18. b) M. W. Hosseini, R. Ruppert, P. Schaeffer, A. De Cian, N. Kyritsakas, J. Fischer, J. Chem. Soc. Chem. Commun. 1994, 2135;
19. c) M. W. Hosseini, G. Brand, P. Schaeffer, R. Ruppert, A. De Cian, J. Fischer, Tetrahedron Lett. 1996, 37, 1405.
20. F. Garcia-Tollado, S. J. Geib, S. Goswami, A. D. Hamilton, J. Am. Chem. Soc. 1991, 113, 9265; Y.-L. Chang, M.-A. West, F. W. Fowler, J. W. Lauther, ibid. 1993, 115, 5991; M. Masuda, T. Shimizu, J. Chem. Soc. Chem. Commun. 1996, 1057; M. D. Hollingsworth, J. C. Santarsiero, H. Oumar-Mahamat, J. C. Nichols, Chem. Mater. 1991, 3, 23; S. Valiyaveettil, V. Enkelmann, K. Müllen, J. Chem. Soc. Chem. Commun. 1994, 2097.
21. F. Garcia-Tollado, S. J. Geib, S. Goswami, A. D. Hamilton, J. Am. Chem. Soc. 1991, 113, 9265; Y.-L. Chang, M.-A. West, F. W. Fowler, J. W. Lauther, ibid. 1993, 115, 5991; M. Masuda, T. Shimizu, J. Chem. Soc. Chem. Commun. 1996, 1057; M. D. Hollingsworth, J. C. Santarsiero, H. Oumar-Mahamat, J. C. Nichols, Chem. Mater. 1991, 3, 23; S. Valiyaveettil, V. Enkelmann, K. Müllen, J. Chem. Soc. Chem. Commun. 1994, 2097.
22. F. Garcia-Tollado, S. J. Geib, S. Goswami, A. D. Hamilton, J. Am. Chem. Soc. 1991, 113, 9265; Y.-L. Chang, M.-A. West, F. W. Fowler, J. W. Lauther, ibid. 1993, 115, 5991; M. Masuda, T. Shimizu, J. Chem. Soc. Chem. Commun. 1996, 1057; M. D. Hollingsworth, J. C. Santarsiero, H. Oumar-Mahamat, J. C. Nichols, Chem. Mater. 1991, 3, 23; S. Valiyaveettil, V. Enkelmann, K. Müllen, J. Chem. Soc. Chem. Commun. 1994, 2097.
23. F. Garcia-Tollado, S. J. Geib, S. Goswami, A. D. Hamilton, J. Am. Chem. Soc. 1991, 113, 9265; Y.-L. Chang, M.-A. West, F. W. Fowler, J. W. Lauther, ibid. 1993, 115, 5991; M. Masuda, T. Shimizu, J. Chem. Soc. Chem. Commun. 1996, 1057; M. D. Hollingsworth, J. C. Santarsiero, H. Oumar-Mahamat, J. C. Nichols, Chem. Mater. 1991, 3, 23; S. Valiyaveettil, V. Enkelmann, K. Müllen, J. Chem. Soc. Chem. Commun. 1994, 2097.
24. F. Garcia-Tollado, S. J. Geib, S. Goswami, A. D. Hamilton, J. Am. Chem. Soc. 1991, 113, 9265; Y.-L. Chang, M.-A. West, F. W. Fowler, J. W. Lauther, ibid. 1993, 115, 5991; M. Masuda, T. Shimizu, J. Chem. Soc. Chem. Commun. 1996, 1057; M. D. Hollingsworth, J. C. Santarsiero, H. Oumar-Mahamat, J. C. Nichols, Chem. Mater. 1991, 3, 23; S. Valiyaveettil, V. Enkelmann, K. Müllen, J. Chem. Soc. Chem. Commun. 1994, 2097.
25. O. Ermer, J. Am. Chem. Soc. 1988, 110, 3747; M. R. Ghadiri, J. R. Granja, R. A. Milligan, D. E. McRee, N. Khazanovich, Nature 1993, 366, 324.
26. O. Ermer, J. Am. Chem. Soc. 1988, 110, 3747; M. R. Ghadiri, J. R. Granja, R. A. Milligan, D. E. McRee, N. Khazanovich, Nature 1993, 366, 324.
27. P. Oxley, W. F. Short J. Chem. Soc. 1947, 497.
28. Kα graphite monochromator. R(F) = 0.055 with 975 reflections (I>3σ(I)). For both structures data were collected at -100 °C with a Philips PW1100/16 automatic diffractometer and analyzed with the Enraf-Nonius SDP/VAX package. The structure was solved by MULTAN; isotropically refined hydrogen atoms were used. Crystallographic data (excluding structure factors) for the structures reported in this paper have been deposited with the Cambridge Crystallographic Data Centre as supplementary publication no. CCDC-179-144. Copies of the data can be obtained free of charge on application to The Director, CCDC, 12 Union Road, Cambridge CB2 1EZ, UK (fax: Int. code +(1223) 336-033: e-mail: deposit@chemcrys.cam.ac.uk).
29. R. Taylor. O. Kennard, Acc. Chem. Res. 1984, 17, 320.
30. K. Yardley, J. Chem. Soc. 1925, 127, 2207; L. G. Roldan, F. J. Rahl, A. R. Paterson, Acta Crystallogr. 1965, 19, 1055; A. L. Bednowitz, B. Post, ibid. 1966, 21, 566.
31. K. Yardley, J. Chem. Soc. 1925, 127, 2207; L. G. Roldan, F. J. Rahl, A. R. Paterson, Acta Crystallogr. 1965, 19, 1055; A. L. Bednowitz, B. Post, ibid. 1966, 21, 566.
32. K. Yardley, J. Chem. Soc. 1925, 127, 2207; L. G. Roldan, F. J. Rahl, A. R. Paterson, Acta Crystallogr. 1965, 19, 1055; A. L. Bednowitz, B. Post, ibid. 1966, 21, 566.