Cocrystals of melamine and succinimide: Supramolecular lattice structure constructed with both self and not-self intermolecular hydrogen bonds

Chemistry Letters

Volumn , Issue 5, 1997, Pages 441-442

  Tukada, Hideyuki ^a   Mazaki, Yasuhiro ^b  

^a YOKOHAMA CITY UNIVERSITY   (Japan)

^b KITASATO UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0031515251     PISSN: 03667022     EISSN: None     Source Type: Journal    
DOI: 10.1246/cl.1997.441     Document Type: Article

References (20)

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3. Reviews, for examples; J.-M. Lehn and A. Rigault, Angew. Chem., Int. Ed. Engl., 27, 1095 (1988); M. C. Etter, Acc. Chem. Res., 23, 120 (1990); G. M. Whitesides, J. P. Mathias and C. T. Seto, Science, 254, 1312 (1991); J. C. MacDonald and G. M. Whitesides, Chem. Rev., 94, 2383, (1994); J. Bernstein, R. E. Davis, L. Shimoni and N.-L. Chang, Angew. Chem., Int. Ed. Engl., 34, 1555 (1995); G. R. Desiraju, Angew. Chem., Int. Ed. Engl., 34, 2331 (1995); C. M. Paleos and D. Tsiourvas, Angew. Chem., Int. Ed. Engl., 34, 1696 (1995); D. Philip and J. F. Stoddart, Angew. Chem., Int. Ed. Engl., 35, 1155 (1996).
4. Reviews, for examples; J.-M. Lehn and A. Rigault, Angew. Chem., Int. Ed. Engl., 27, 1095 (1988); M. C. Etter, Acc. Chem. Res., 23, 120 (1990); G. M. Whitesides, J. P. Mathias and C. T. Seto, Science, 254, 1312 (1991); J. C. MacDonald and G. M. Whitesides, Chem. Rev., 94, 2383, (1994); J. Bernstein, R. E. Davis, L. Shimoni and N.-L. Chang, Angew. Chem., Int. Ed. Engl., 34, 1555 (1995); G. R. Desiraju, Angew. Chem., Int. Ed. Engl., 34, 2331 (1995); C. M. Paleos and D. Tsiourvas, Angew. Chem., Int. Ed. Engl., 34, 1696 (1995); D. Philip and J. F. Stoddart, Angew. Chem., Int. Ed. Engl., 35, 1155 (1996).
5. Reviews, for examples; J.-M. Lehn and A. Rigault, Angew. Chem., Int. Ed. Engl., 27, 1095 (1988); M. C. Etter, Acc. Chem. Res., 23, 120 (1990); G. M. Whitesides, J. P. Mathias and C. T. Seto, Science, 254, 1312 (1991); J. C. MacDonald and G. M. Whitesides, Chem. Rev., 94, 2383, (1994); J. Bernstein, R. E. Davis, L. Shimoni and N.-L. Chang, Angew. Chem., Int. Ed. Engl., 34, 1555 (1995); G. R. Desiraju, Angew. Chem., Int. Ed. Engl., 34, 2331 (1995); C. M. Paleos and D. Tsiourvas, Angew. Chem., Int. Ed. Engl., 34, 1696 (1995); D. Philip and J. F. Stoddart, Angew. Chem., Int. Ed. Engl., 35, 1155 (1996).
6. Reviews, for examples; J.-M. Lehn and A. Rigault, Angew. Chem., Int. Ed. Engl., 27, 1095 (1988); M. C. Etter, Acc. Chem. Res., 23, 120 (1990); G. M. Whitesides, J. P. Mathias and C. T. Seto, Science, 254, 1312 (1991); J. C. MacDonald and G. M. Whitesides, Chem. Rev., 94, 2383, (1994); J. Bernstein, R. E. Davis, L. Shimoni and N.-L. Chang, Angew. Chem., Int. Ed. Engl., 34, 1555 (1995); G. R. Desiraju, Angew. Chem., Int. Ed. Engl., 34, 2331 (1995); C. M. Paleos and D. Tsiourvas, Angew. Chem., Int. Ed. Engl., 34, 1696 (1995); D. Philip and J. F. Stoddart, Angew. Chem., Int. Ed. Engl., 35, 1155 (1996).
7. Reviews, for examples; J.-M. Lehn and A. Rigault, Angew. Chem., Int. Ed. Engl., 27, 1095 (1988); M. C. Etter, Acc. Chem. Res., 23, 120 (1990); G. M. Whitesides, J. P. Mathias and C. T. Seto, Science, 254, 1312 (1991); J. C. MacDonald and G. M. Whitesides, Chem. Rev., 94, 2383, (1994); J. Bernstein, R. E. Davis, L. Shimoni and N.-L. Chang, Angew. Chem., Int. Ed. Engl., 34, 1555 (1995); G. R. Desiraju, Angew. Chem., Int. Ed. Engl., 34, 2331 (1995); C. M. Paleos and D. Tsiourvas, Angew. Chem., Int. Ed. Engl., 34, 1696 (1995); D. Philip and J. F. Stoddart, Angew. Chem., Int. Ed. Engl., 35, 1155 (1996).
8. Reviews, for examples; J.-M. Lehn and A. Rigault, Angew. Chem., Int. Ed. Engl., 27, 1095 (1988); M. C. Etter, Acc. Chem. Res., 23, 120 (1990); G. M. Whitesides, J. P. Mathias and C. T. Seto, Science, 254, 1312 (1991); J. C. MacDonald and G. M. Whitesides, Chem. Rev., 94, 2383, (1994); J. Bernstein, R. E. Davis, L. Shimoni and N.-L. Chang, Angew. Chem., Int. Ed. Engl., 34, 1555 (1995); G. R. Desiraju, Angew. Chem., Int. Ed. Engl., 34, 2331 (1995); C. M. Paleos and D. Tsiourvas, Angew. Chem., Int. Ed. Engl., 34, 1696 (1995); D. Philip and J. F. Stoddart, Angew. Chem., Int. Ed. Engl., 35, 1155 (1996).
9. Complexes of 2-aminopyridines and imides, for examples; C. T. Seto and G. M. Whitesides, J. Am. Chem. Soc., 112, 6409 (1990) and 113, 712 (1991); K. Hanabusa, T. Miki, Y. Taguchi, T. Koyama, and H. Shirai, J. Chem. Soc., Chem. Commun., 1993, 1382; K. Kurihara, K. Ohta, Y. Tanaka, Y. Aoyama and T. Kunitake, J. Am. Chem. Soc., 113, 444 (1991); Y. Ikeura, K. Kurihara and T. Kunitake, J. Am. Chem. Soc., 113, 7342 (1991); J.-M. Lehn, M. Mascal, A. Decian and J. Fisher, J. Chem. Soc., Chem. Commun., 1990, 479; J.-M. Lehn, Makromol. Chem. Macromol. Symp., 69, 1 (1993); T. M. Bohanon, S. Denzinger, R. Fink, W. Paulus, H. Ringdorf and M. Weck, Angew. Chem., Int. Ed. Engl., 34, 58 (1995); S. A. Benner, J. A. Piccirilli, T. Kraunch and S. E. Moroney, Nature, 343, 33 (1990).
10. Complexes of 2-aminopyridines and imides, for examples; C. T. Seto and G. M. Whitesides, J. Am. Chem. Soc., 112, 6409 (1990) and 113, 712 (1991); K. Hanabusa, T. Miki, Y. Taguchi, T. Koyama, and H. Shirai, J. Chem. Soc., Chem. Commun., 1993, 1382; K. Kurihara, K. Ohta, Y. Tanaka, Y. Aoyama and T. Kunitake, J. Am. Chem. Soc., 113, 444 (1991); Y. Ikeura, K. Kurihara and T. Kunitake, J. Am. Chem. Soc., 113, 7342 (1991); J.-M. Lehn, M. Mascal, A. Decian and J. Fisher, J. Chem. Soc., Chem. Commun., 1990, 479; J.-M. Lehn, Makromol. Chem. Macromol. Symp., 69, 1 (1993); T. M. Bohanon, S. Denzinger, R. Fink, W. Paulus, H. Ringdorf and M. Weck, Angew. Chem., Int. Ed. Engl., 34, 58 (1995); S. A. Benner, J. A. Piccirilli, T. Kraunch and S. E. Moroney, Nature, 343, 33 (1990).
11. Complexes of 2-aminopyridines and imides, for examples; C. T. Seto and G. M. Whitesides, J. Am. Chem. Soc., 112, 6409 (1990) and 113, 712 (1991); K. Hanabusa, T. Miki, Y. Taguchi, T. Koyama, and H. Shirai, J. Chem. Soc., Chem. Commun., 1993, 1382; K. Kurihara, K. Ohta, Y. Tanaka, Y. Aoyama and T. Kunitake, J. Am. Chem. Soc., 113, 444 (1991); Y. Ikeura, K. Kurihara and T. Kunitake, J. Am. Chem. Soc., 113, 7342 (1991); J.-M. Lehn, M. Mascal, A. Decian and J. Fisher, J. Chem. Soc., Chem. Commun., 1990, 479; J.-M. Lehn, Makromol. Chem. Macromol. Symp., 69, 1 (1993); T. M. Bohanon, S. Denzinger, R. Fink, W. Paulus, H. Ringdorf and M. Weck, Angew. Chem., Int. Ed. Engl., 34, 58 (1995); S. A. Benner, J. A. Piccirilli, T. Kraunch and S. E. Moroney, Nature, 343, 33 (1990).
12. Complexes of 2-aminopyridines and imides, for examples; C. T. Seto and G. M. Whitesides, J. Am. Chem. Soc., 112, 6409 (1990) and 113, 712 (1991); K. Hanabusa, T. Miki, Y. Taguchi, T. Koyama, and H. Shirai, J. Chem. Soc., Chem. Commun., 1993, 1382; K. Kurihara, K. Ohta, Y. Tanaka, Y. Aoyama and T. Kunitake, J. Am. Chem. Soc., 113, 444 (1991); Y. Ikeura, K. Kurihara and T. Kunitake, J. Am. Chem. Soc., 113, 7342 (1991); J.-M. Lehn, M. Mascal, A. Decian and J. Fisher, J. Chem. Soc., Chem. Commun., 1990, 479; J.-M. Lehn, Makromol. Chem. Macromol. Symp., 69, 1 (1993); T. M. Bohanon, S. Denzinger, R. Fink, W. Paulus, H. Ringdorf and M. Weck, Angew. Chem., Int. Ed. Engl., 34, 58 (1995); S. A. Benner, J. A. Piccirilli, T. Kraunch and S. E. Moroney, Nature, 343, 33 (1990).
13. Complexes of 2-aminopyridines and imides, for examples; C. T. Seto and G. M. Whitesides, J. Am. Chem. Soc., 112, 6409 (1990) and 113, 712 (1991); K. Hanabusa, T. Miki, Y. Taguchi, T. Koyama, and H. Shirai, J. Chem. Soc., Chem. Commun., 1993, 1382; K. Kurihara, K. Ohta, Y. Tanaka, Y. Aoyama and T. Kunitake, J. Am. Chem. Soc., 113, 444 (1991); Y. Ikeura, K. Kurihara and T. Kunitake, J. Am. Chem. Soc., 113, 7342 (1991); J.-M. Lehn, M. Mascal, A. Decian and J. Fisher, J. Chem. Soc., Chem. Commun., 1990, 479; J.-M. Lehn, Makromol. Chem. Macromol. Symp., 69, 1 (1993); T. M. Bohanon, S. Denzinger, R. Fink, W. Paulus, H. Ringdorf and M. Weck, Angew. Chem., Int. Ed. Engl., 34, 58 (1995); S. A. Benner, J. A. Piccirilli, T. Kraunch and S. E. Moroney, Nature, 343, 33 (1990).
14. Complexes of 2-aminopyridines and imides, for examples; C. T. Seto and G. M. Whitesides, J. Am. Chem. Soc., 112, 6409 (1990) and 113, 712 (1991); K. Hanabusa, T. Miki, Y. Taguchi, T. Koyama, and H. Shirai, J. Chem. Soc., Chem. Commun., 1993, 1382; K. Kurihara, K. Ohta, Y. Tanaka, Y. Aoyama and T. Kunitake, J. Am. Chem. Soc., 113, 444 (1991); Y. Ikeura, K. Kurihara and T. Kunitake, J. Am. Chem. Soc., 113, 7342 (1991); J.-M. Lehn, M. Mascal, A. Decian and J. Fisher, J. Chem. Soc., Chem. Commun., 1990, 479; J.-M. Lehn, Makromol. Chem. Macromol. Symp., 69, 1 (1993); T. M. Bohanon, S. Denzinger, R. Fink, W. Paulus, H. Ringdorf and M. Weck, Angew. Chem., Int. Ed. Engl., 34, 58 (1995); S. A. Benner, J. A. Piccirilli, T. Kraunch and S. E. Moroney, Nature, 343, 33 (1990).
15. Complexes of 2-aminopyridines and imides, for examples; C. T. Seto and G. M. Whitesides, J. Am. Chem. Soc., 112, 6409 (1990) and 113, 712 (1991); K. Hanabusa, T. Miki, Y. Taguchi, T. Koyama, and H. Shirai, J. Chem. Soc., Chem. Commun., 1993, 1382; K. Kurihara, K. Ohta, Y. Tanaka, Y. Aoyama and T. Kunitake, J. Am. Chem. Soc., 113, 444 (1991); Y. Ikeura, K. Kurihara and T. Kunitake, J. Am. Chem. Soc., 113, 7342 (1991); J.-M. Lehn, M. Mascal, A. Decian and J. Fisher, J. Chem. Soc., Chem. Commun., 1990, 479; J.-M. Lehn, Makromol. Chem. Macromol. Symp., 69, 1 (1993); T. M. Bohanon, S. Denzinger, R. Fink, W. Paulus, H. Ringdorf and M. Weck, Angew. Chem., Int. Ed. Engl., 34, 58 (1995); S. A. Benner, J. A. Piccirilli, T. Kraunch and S. E. Moroney, Nature, 343, 33 (1990).
16. Complexes of 2-aminopyridines and imides, for examples; C. T. Seto and G. M. Whitesides, J. Am. Chem. Soc., 112, 6409 (1990) and 113, 712 (1991); K. Hanabusa, T. Miki, Y. Taguchi, T. Koyama, and H. Shirai, J. Chem. Soc., Chem. Commun., 1993, 1382; K. Kurihara, K. Ohta, Y. Tanaka, Y. Aoyama and T. Kunitake, J. Am. Chem. Soc., 113, 444 (1991); Y. Ikeura, K. Kurihara and T. Kunitake, J. Am. Chem. Soc., 113, 7342 (1991); J.-M. Lehn, M. Mascal, A. Decian and J. Fisher, J. Chem. Soc., Chem. Commun., 1990, 479; J.-M. Lehn, Makromol. Chem. Macromol. Symp., 69, 1 (1993); T. M. Bohanon, S. Denzinger, R. Fink, W. Paulus, H. Ringdorf and M. Weck, Angew. Chem., Int. Ed. Engl., 34, 58 (1995); S. A. Benner, J. A. Piccirilli, T. Kraunch and S. E. Moroney, Nature, 343, 33 (1990).
17. Complexes of 2-aminopyridines and imides, for examples; C. T. Seto and G. M. Whitesides, J. Am. Chem. Soc., 112, 6409 (1990) and 113, 712 (1991); K. Hanabusa, T. Miki, Y. Taguchi, T. Koyama, and H. Shirai, J. Chem. Soc., Chem. Commun., 1993, 1382; K. Kurihara, K. Ohta, Y. Tanaka, Y. Aoyama and T. Kunitake, J. Am. Chem. Soc., 113, 444 (1991); Y. Ikeura, K. Kurihara and T. Kunitake, J. Am. Chem. Soc., 113, 7342 (1991); J.-M. Lehn, M. Mascal, A. Decian and J. Fisher, J. Chem. Soc., Chem. Commun., 1990, 479; J.-M. Lehn, Makromol. Chem. Macromol. Symp., 69, 1 (1993); T. M. Bohanon, S. Denzinger, R. Fink, W. Paulus, H. Ringdorf and M. Weck, Angew. Chem., Int. Ed. Engl., 34, 58 (1995); S. A. Benner, J. A. Piccirilli, T. Kraunch and S. E. Moroney, Nature, 343, 33 (1990).
18. 6 by varying the ratio of 1 / 2.
19. w = 0.063 by the UNICS-III program.
20. Similar diversity is expected for the cocrystals of 2-aminopyrimidine and carboxylic acids; M, C. Etter and D. A. Adsmond, J. Chem. Soc., Chem. Commun., 1990, 589.