Solvent-induced polymorphism of three-dimensional hydrogen-bonded networks of hexakis(4-carbamoylphenyl)benzene

Journal of the American Chemical Society

Volumn 125, Issue 10, 2003, Pages 3035-3045

  Kobayashi, Kenji ^a   Sato, Azumi ^b   Sakamoto, Shigeru ^c   Yamaguchi, Kentaro ^c  

^a SHIZUOKA UNIVERSITY   (Japan)

^b UNIVERSITY OF TSUKUBA   (Japan)

^c CHIBA UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

CRYSTAL STRUCTURE; CRYSTALLIZATION; DIMERS; HYDROGEN BONDS; HYDROTHERMAL SYNTHESIS; MIXTURES; MOLECULAR DYNAMICS; SOLVENTS;

POLYMORPHISM;

BENZENE;

AMIDE; BENZENE DERIVATIVE; DIMER; DIMETHYL SULFOXIDE; HEXAKIS(4 CARBAMOYLPHENYL)BENZENE; SOLVENT; UNCLASSIFIED DRUG;

ARTICLE; CRYSTAL STRUCTURE; CRYSTALLIZATION; HYDROGEN BOND; ISOMERISM; POROSITY; STRUCTURE ANALYSIS;

EID: 0037433550     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja0293103     Document Type: Article

References (103)

1. (a) Lehn, J.-M. Supramolecular Chemistry: Concepts and Perspectives; VCH: Weinheim, Germany, 1995.
2. (b) Leininger, S.; Olenyuk, B.; Stang, P. J. Chem. Rev. 2000, 100, 853-908.
3. (c) Prins, L. J.; Reinhoudt, D. N.; Timmerman, P. Angew. Chem., Int. Ed. 2001, 40, 2382-2426.
4. (a) Desiraju, G. R. Crystal Engineering: The Design of Organic Solids; Elsevier: Amsterdam, 1989.
5. (b) Etter, M. C. Acc. Chem. Res. 1990, 23, 120-126.
6. (c) Desiraju, G. R. Angew. Chem., Int. Ed. Engl. 1995, 34, 2311-2327.
7. (d) Comprehensive Supramolecular Chemistry, Solid-State Supramolecular Chemistry: Crystal Engineering; MacNicol, D. D., Toda, F., Bishop, R., Eds.; Pergamon: New York, 1996; Vol. 6.
8. (e) Zaworotko, M. J. Chem., Commun. 2001, 1-9.
9. (f) Steiner, T. Angew. Chem., Int. Ed. 2002, 41, 48-76.
10. (a) Endo, K.; Sawaki, T.; Koyanagi, M.; Kobayashi, K.; Masuda, H.; Aoyama, Y. J. Am. Chem. Soc. 1995, 117, 8341-8352.
11. (b) Holman, K. T.; Pivovar, A. M.; Swift, J. A.; Ward, M. D. Acc. Chem. Res. 2000, 34, 107-118.
12. (a) Eddaoudi, M.; Moler, D. B.; Li, H.; Chen, B.; Reineke, T. M.; O'Keeffe, M.; Yaghi, O. M. Acc. Chem. Res. 2001, 34, 319-330.
13. (b) Noro, S.; Kitagawa, S.; Kondo, M.; Seki, K. Angew. Chem., Int. Ed. 2000, 39, 2082-2084.
14. (a) Fujita, M.; Kwon, Y. J.; Washizu, S.; Ogura, K. J. Am. Chem. Soc. 1994, 116, 1151-1152.
15. (b) Endo, K.; Koike, T.; Sawaki, T.; Hayashida, O.; Masuda, H.; Aoyama, Y. J. Am. Chem. Soc. 1997, 119, 4117-4122.
16. (c) Sawaki, T.; Endo, K.; Kobayashi, K.; Hayashida, O.; Aoyama, Y. Bull. Chem. Soc. Jpn. 1997, 70, 3075-3079.
17. (d) Seo, J. S.; Whang, D.; Lee, H.; Jun, S. I.; Oh, J.; Jeon, Y. J.; Kim, K. Nature 2000, 404, 982-986.
18. (a) Organic Molecular Solids: Properties and Applications; Jones, W., Ed.: CRC Press: Boca Raton, FL, 1997.
19. (b) Thalladi, V. R.; Brasselet, S.; Weiss, H.-C.; Bläser, D.; Katz, A. K.; Carrell, H. L.; Boese, R.; Zyss, J.; Nangia, A.; Desiraju, G. R. J. Am. Chem. Soc. 1998, 120, 2563-2577.
20. (c) Coronado, E.; Galán-Mascarós, J. R.; Gómez-García, C. J.; Laukhin, V. Nature 2000, 408, 447-449.
21. (a) Sharma, C. V. K.; Zaworotko, M. J. Chem. Commun. 1996, 2655-2656.
22. (b) Batten, S. R.; Robson, R. Angew. Chem., Int. Ed. Engl. 1998, 37, 1460-1494.
23. Dewa, T.; Endo, K.; Aoyama, Y. J. Am. Chem. Soc. 1998, 120, 8933-8940.
24. Kolotuchin, S. V.; Fenlon, E. E.; Wilson, S. R.; Loweth, C. J.; Zimmerman, S. C. Angew. Chem., Int. Ed. Engl. 1995, 34, 2654-2657.
25. (a) Ghadiri, M. R.; Granja, J. R.; Milligan, R. A.; McRee, D. E.; Khazanovich, N. Nature 1993, 366, 324-327.
26. (b) Venkataraman, D.; Lee, S.; Zhang, J.; Moore, J. S. Nature 1994, 371, 591-593.
27. (c) MacGillivray, L. R.; Atwood, J. L. J. Am. Chem. Soc. 1997, 119, 6931-6932.
28. (d) Kobayashi, K.; Shirasaka, T.; Horn, E.; Furukawa, N. Tetrahedron Lett. 1999, 40, 8883-8886.
29. (e) Bong, D. T.; Clark, T. D.; Granja, J. R.; Ghadiri, M. R. Angew. Chem., Int. Ed. 2001, 40, 988-1011.
30. (a) Russell, V. A.; Evans, C. C.; Li, W.; Ward, M. D. Science 1997, 276, 575-579.
31. (b) Holman, K. T.; Martin, S. M.; Parker, D. P.; Ward, M. D. J. Am. Chem. Soc. 2001, 123. 4421-4431.
32. (a) Kobayashi, K.; Endo, K.; Aoyama, Y.; Masuda, H. Tetrahedron Lett. 1993, 34, 7929-7932.
33. (b) Kobayashi, K.; Koyanagi, M.; Endo, K.; Masuda, H.; Aoyama, Y. Chem. Eur. J. 1998, 4, 417-424.
34. Sada, K.; Sugahara, M.; Kato, K.; Miyata, M. J. Am. Chem. Soc. 2001, 123, 4386-4392 and references therein.
35. (a) Kobayashi, K.; Shirasaka, T.; Sato, A.; Horn, E.; Furukawa, N. Angew. Chem., Int. Ed. 1999, 38, 3483-3486.
36. (b) Kobayashi, K.; Shirasaka, T.; Horn, E.; Furukawa, N. Tetrahedron Lett. 2000, 41, 89-93.
37. For hexaarylbenzene derivatives, see: Watson, M. D.; Fechtenkötter, A.; Müllen, K. Chem. Rev. 2001, 101, 1267-1300.
38. For the hexakis-host clathrates which are based on benzene rings hexasubstituted by flexible but bulky sidearms such as arylthio groups, see: MacNicol, D. D.; Downing, G. A. In Comprehensive Supramolecular Chemistry, Solid-State Supramolecular Chemistry: Crystal Engineering; MacNicol, D. D., Toda, F., Bishop, R., Eds.; Pergamon: New York, 1996; Vol. 6, pp 421-464.
39. For 3-D hydrogen-bonded networks with self-interpenetration based on tetrahedral (diamondoid)-type and octahedral-type hosts, see: (a) Ermer, O. J. Am. Chem. Soc. 1988, 110, 3747-3754. (b) Ermer, O.; Lindenberg, L. Helv. Chim. Acta 1991, 74, 825-877. (c) Simard, M.; Su, D.; Wuest, J. D. J. Am. Chem. Soc. 1991, 113, 4696-4698. (d) Brunet, P.; Simard, M.; Wuest, J. D. J. Am. Chem. Soc. 1997, 119, 2737-2738. (e) Reddy, D. S.; Dewa, T.; Endo, K.; Aoyama, Y. Angew. Chem., Int. Ed. 2000, 39, 4266-4268. (f) Thaimattam, R.; Xue, F.; Sarma, J. A. R. P.; Mak, T. C. W.; Desiraju, G. R. J. Am. Chem. Soc. 2001, 123, 4432-4445. (g) Vaid, T. P.; Sydora, O. L.; Douthwaite, R. E.; Wolczanski, P. T.; Lobkovsky, E. B. Chem. Commun. 2001, 1300-1301.
40. For 3-D hydrogen-bonded networks with self-interpenetration based on tetrahedral (diamondoid)-type and octahedral-type hosts, see: (a) Ermer, O. J. Am. Chem. Soc. 1988, 110, 3747-3754. (b) Ermer, O.; Lindenberg, L. Helv. Chim. Acta 1991, 74, 825-877. (c) Simard, M.; Su, D.; Wuest, J. D. J. Am. Chem. Soc. 1991, 113, 4696-4698. (d) Brunet, P.; Simard, M.; Wuest, J. D. J. Am. Chem. Soc. 1997, 119, 2737-2738. (e) Reddy, D. S.; Dewa, T.; Endo, K.; Aoyama, Y. Angew. Chem., Int. Ed. 2000, 39, 4266-4268. (f) Thaimattam, R.; Xue, F.; Sarma, J. A. R. P.; Mak, T. C. W.; Desiraju, G. R. J. Am. Chem. Soc. 2001, 123, 4432-4445. (g) Vaid, T. P.; Sydora, O. L.; Douthwaite, R. E.; Wolczanski, P. T.; Lobkovsky, E. B. Chem. Commun. 2001, 1300-1301.
41. For 3-D hydrogen-bonded networks with self-interpenetration based on tetrahedral (diamondoid)-type and octahedral-type hosts, see: (a) Ermer, O. J. Am. Chem. Soc. 1988, 110, 3747-3754. (b) Ermer, O.; Lindenberg, L. Helv. Chim. Acta 1991, 74, 825-877. (c) Simard, M.; Su, D.; Wuest, J. D. J. Am. Chem. Soc. 1991, 113, 4696-4698. (d) Brunet, P.; Simard, M.; Wuest, J. D. J. Am. Chem. Soc. 1997, 119, 2737-2738. (e) Reddy, D. S.; Dewa, T.; Endo, K.; Aoyama, Y. Angew. Chem., Int. Ed. 2000, 39, 4266-4268. (f) Thaimattam, R.; Xue, F.; Sarma, J. A. R. P.; Mak, T. C. W.; Desiraju, G. R. J. Am. Chem. Soc. 2001, 123, 4432-4445. (g) Vaid, T. P.; Sydora, O. L.; Douthwaite, R. E.; Wolczanski, P. T.; Lobkovsky, E. B. Chem. Commun. 2001, 1300-1301.
42. For 3-D hydrogen-bonded networks with self-interpenetration based on tetrahedral (diamondoid)-type and octahedral-type hosts, see: (a) Ermer, O. J. Am. Chem. Soc. 1988, 110, 3747-3754. (b) Ermer, O.; Lindenberg, L. Helv. Chim. Acta 1991, 74, 825-877. (c) Simard, M.; Su, D.; Wuest, J. D. J. Am. Chem. Soc. 1991, 113, 4696-4698. (d) Brunet, P.; Simard, M.; Wuest, J. D. J. Am. Chem. Soc. 1997, 119, 2737-2738. (e) Reddy, D. S.; Dewa, T.; Endo, K.; Aoyama, Y. Angew. Chem., Int. Ed. 2000, 39, 4266-4268. (f) Thaimattam, R.; Xue, F.; Sarma, J. A. R. P.; Mak, T. C. W.; Desiraju, G. R. J. Am. Chem. Soc. 2001, 123, 4432-4445. (g) Vaid, T. P.; Sydora, O. L.; Douthwaite, R. E.; Wolczanski, P. T.; Lobkovsky, E. B. Chem. Commun. 2001, 1300-1301.
43. For 3-D hydrogen-bonded networks with self-interpenetration based on tetrahedral (diamondoid)-type and octahedral-type hosts, see: (a) Ermer, O. J. Am. Chem. Soc. 1988, 110, 3747-3754. (b) Ermer, O.; Lindenberg, L. Helv. Chim. Acta 1991, 74, 825-877. (c) Simard, M.; Su, D.; Wuest, J. D. J. Am. Chem. Soc. 1991, 113, 4696-4698. (d) Brunet, P.; Simard, M.; Wuest, J. D. J. Am. Chem. Soc. 1997, 119, 2737-2738. (e) Reddy, D. S.; Dewa, T.; Endo, K.; Aoyama, Y. Angew. Chem., Int. Ed. 2000, 39, 4266-4268. (f) Thaimattam, R.; Xue, F.; Sarma, J. A. R. P.; Mak, T. C. W.; Desiraju, G. R. J. Am. Chem. Soc. 2001, 123, 4432-4445. (g) Vaid, T. P.; Sydora, O. L.; Douthwaite, R. E.; Wolczanski, P. T.; Lobkovsky, E. B. Chem. Commun. 2001, 1300-1301.
44. For 3-D hydrogen-bonded networks with self-interpenetration based on tetrahedral (diamondoid)-type and octahedral-type hosts, see: (a) Ermer, O. J. Am. Chem. Soc. 1988, 110, 3747-3754. (b) Ermer, O.; Lindenberg, L. Helv. Chim. Acta 1991, 74, 825-877. (c) Simard, M.; Su, D.; Wuest, J. D. J. Am. Chem. Soc. 1991, 113, 4696-4698. (d) Brunet, P.; Simard, M.; Wuest, J. D. J. Am. Chem. Soc. 1997, 119, 2737-2738. (e) Reddy, D. S.; Dewa, T.; Endo, K.; Aoyama, Y. Angew. Chem., Int. Ed. 2000, 39, 4266-4268. (f) Thaimattam, R.; Xue, F.; Sarma, J. A. R. P.; Mak, T. C. W.; Desiraju, G. R. J. Am. Chem. Soc. 2001, 123, 4432-4445. (g) Vaid, T. P.; Sydora, O. L.; Douthwaite, R. E.; Wolczanski, P. T.; Lobkovsky, E. B. Chem. Commun. 2001, 1300-1301.
45. For 3-D hydrogen-bonded networks with self-interpenetration based on tetrahedral (diamondoid)-type and octahedral-type hosts, see: (a) Ermer, O. J. Am. Chem. Soc. 1988, 110, 3747-3754. (b) Ermer, O.; Lindenberg, L. Helv. Chim. Acta 1991, 74, 825-877. (c) Simard, M.; Su, D.; Wuest, J. D. J. Am. Chem. Soc. 1991, 113, 4696-4698. (d) Brunet, P.; Simard, M.; Wuest, J. D. J. Am. Chem. Soc. 1997, 119, 2737-2738. (e) Reddy, D. S.; Dewa, T.; Endo, K.; Aoyama, Y. Angew. Chem., Int. Ed. 2000, 39, 4266-4268. (f) Thaimattam, R.; Xue, F.; Sarma, J. A. R. P.; Mak, T. C. W.; Desiraju, G. R. J. Am. Chem. Soc. 2001, 123, 4432-4445. (g) Vaid, T. P.; Sydora, O. L.; Douthwaite, R. E.; Wolczanski, P. T.; Lobkovsky, E. B. Chem. Commun. 2001, 1300-1301.
46. For hydrogen-bonding motifs of the primary amide group, see: (a) Leiserowitz, L.; Schmidt, G. M. J. J. Chem. Soc. A 1969, 2372-2382. (b) Blake, C., C. F.; Small, R. W. H. Acta Crystallogr. 1972, B28, 2201-2206. (c) Cobbledick, R. E.; Small, R. W. H. Acta Crystallogr. 1972, B28, 2893-2896. (d) Berkovitch-Yellin, Z.; Leiserowitz, L. J. Am. Chem. Soc. 1980, 102, 7677-7690. (e) Leiserowitz, L.; Hagler, A. T. Proc. R. Soc. London 1983, A388, 133-175. (f) Aakeröy, C. B.; Beatty, A. M. Chem. Commun. 1998, 1067-1068. (g) Edgar, R.; Schultz, T. M.; Rasmussen, F. B.; Feidenhans' I.R. ; Leiserowitz, L. J. Am. Chem. Soc. 1999, 121, 632-637. (h) Kobko, N.; Paraskevas, L.; del Rio, E.; Dannenberg, J. J. J. Am. Chem. Soc. 2001, 123, 4348-4349.
47. For hydrogen-bonding motifs of the primary amide group, see: (a) Leiserowitz, L.; Schmidt, G. M. J. J. Chem. Soc. A 1969, 2372-2382. (b) Blake, C. C. F.; Small, R. W. H. Acta Crystallogr. 1972, B28, 2201-2206. (c) Cobbledick, R. E.; Small, R. W. H. Acta Crystallogr. 1972, B28, 2893-2896. (d) Berkovitch-Yellin, Z.; Leiserowitz, L. J. Am. Chem. Soc. 1980, 102, 7677-7690. (e) Leiserowitz, L.; Hagler, A. T. Proc. R. Soc. London 1983, A388, 133-175. (f) Aakeröy, C. B.; Beatty, A. M. Chem. Commun. 1998, 1067-1068. (g) Edgar, R.; Schultz, T. M.; Rasmussen, F. B.; Feidenhans' I.R. ; Leiserowitz, L. J. Am. Chem. Soc. 1999, 121, 632-637. (h) Kobko, N.; Paraskevas, L.; del Rio, E.; Dannenberg, J. J. J. Am. Chem. Soc. 2001, 123, 4348-4349.
48. For hydrogen-bonding motifs of the primary amide group, see: (a) Leiserowitz, L.; Schmidt, G. M. J. J. Chem. Soc. A 1969, 2372-2382. (b) Blake, C., C. F.; Small, R. W. H. Acta Crystallogr. 1972, B28, 2201-2206. (c) Cobbledick, R. E.; Small, R. W. H. Acta Crystallogr. 1972, B28, 2893-2896. (d) Berkovitch-Yellin, Z.; Leiserowitz, L. J. Am. Chem. Soc. 1980, 102, 7677-7690. (e) Leiserowitz, L.; Hagler, A. T. Proc. R. Soc. London 1983, A388, 133-175. (f) Aakeröy, C. B.; Beatty, A. M. Chem. Commun. 1998, 1067-1068. (g) Edgar, R.; Schultz, T. M.; Rasmussen, F. B.; Feidenhans' I.R. ; Leiserowitz, L. J. Am. Chem. Soc. 1999, 121, 632-637. (h) Kobko, N.; Paraskevas, L.; del Rio, E.; Dannenberg, J. J. J. Am. Chem. Soc. 2001, 123, 4348-4349.
49. For hydrogen-bonding motifs of the primary amide group, see: (a) Leiserowitz, L.; Schmidt, G. M. J. J. Chem. Soc. A 1969, 2372-2382. (b) Blake, C., C. F.; Small, R. W. H. Acta Crystallogr. 1972, B28, 2201-2206. (c) Cobbledick, R. E.; Small, R. W. H. Acta Crystallogr. 1972, B28, 2893-2896. (d) Berkovitch-Yellin, Z.; Leiserowitz, L. J. Am. Chem. Soc. 1980, 102, 7677-7690. (e) Leiserowitz, L.; Hagler, A. T. Proc. R. Soc. London 1983, A388, 133-175. (f) Aakeröy, C. B.; Beatty, A. M. Chem. Commun. 1998, 1067-1068. (g) Edgar, R.; Schultz, T. M.; Rasmussen, F. B.; Feidenhans' I.R. ; Leiserowitz, L. J. Am. Chem. Soc. 1999, 121, 632-637. (h) Kobko, N.; Paraskevas, L.; del Rio, E.; Dannenberg, J. J. J. Am. Chem. Soc. 2001, 123, 4348-4349.
50. For hydrogen-bonding motifs of the primary amide group, see: (a) Leiserowitz, L.; Schmidt, G. M. J. J. Chem. Soc. A 1969, 2372-2382. (b) Blake, C., C. F.; Small, R. W. H. Acta Crystallogr. 1972, B28, 2201-2206. (c) Cobbledick, R. E.; Small, R. W. H. Acta Crystallogr. 1972, B28, 2893-2896. (d) Berkovitch-Yellin, Z.; Leiserowitz, L. J. Am. Chem. Soc. 1980, 102, 7677-7690. (e) Leiserowitz, L.; Hagler, A. T. Proc. R. Soc. London 1983, A388, 133-175. (f) Aakeröy, C. B.; Beatty, A. M. Chem. Commun. 1998, 1067-1068. (g) Edgar, R.; Schultz, T. M.; Rasmussen, F. B.; Feidenhans' I.R. ; Leiserowitz, L. J. Am. Chem. Soc. 1999, 121, 632-637. (h) Kobko, N.; Paraskevas, L.; del Rio, E.; Dannenberg, J. J. J. Am. Chem. Soc. 2001, 123, 4348-4349.
51. For hydrogen-bonding motifs of the primary amide group, see: (a) Leiserowitz, L.; Schmidt, G. M. J. J. Chem. Soc. A 1969, 2372-2382. (b) Blake, C., C. F.; Small, R. W. H. Acta Crystallogr. 1972, B28, 2201-2206. (c) Cobbledick, R. E.; Small, R. W. H. Acta Crystallogr. 1972, B28, 2893-2896. (d) Berkovitch-Yellin, Z.; Leiserowitz, L. J. Am. Chem. Soc. 1980, 102, 7677-7690. (e) Leiserowitz, L.; Hagler, A. T. Proc. R. Soc. London 1983, A388, 133-175. (f) Aakeröy, C. B.; Beatty, A. M. Chem. Commun. 1998, 1067-1068. (g) Edgar, R.; Schultz, T. M.; Rasmussen, F. B.; Feidenhans' I.R. ; Leiserowitz, L. J. Am. Chem. Soc. 1999, 121, 632-637. (h) Kobko, N.; Paraskevas, L.; del Rio, E.; Dannenberg, J. J. J. Am. Chem. Soc. 2001, 123, 4348-4349.
52. For hydrogen-bonding motifs of the primary amide group, see: (a) Leiserowitz, L.; Schmidt, G. M. J. J. Chem. Soc. A 1969, 2372-2382. (b) Blake, C., C. F.; Small, R. W. H. Acta Crystallogr. 1972, B28, 2201-2206. (c) Cobbledick, R. E.; Small, R. W. H. Acta Crystallogr. 1972, B28, 2893-2896. (d) Berkovitch-Yellin, Z.; Leiserowitz, L. J. Am. Chem. Soc. 1980, 102, 7677-7690. (e) Leiserowitz, L.; Hagler, A. T. Proc. R. Soc. London 1983, A388, 133-175. (f) Aakeröy, C. B.; Beatty, A. M. Chem. Commun. 1998, 1067-1068. (g) Edgar, R.; Schultz, T. M.; Rasmussen, F. B.; Feidenhans' I.R. ; Leiserowitz, L. J. Am. Chem. Soc. 1999, 121, 632-637. (h) Kobko, N.; Paraskevas, L.; del Rio, E.; Dannenberg, J. J. J. Am. Chem. Soc. 2001, 123, 4348-4349.
53. For hydrogen-bonding motifs of the primary amide group, see: (a) Leiserowitz, L.; Schmidt, G. M. J. J. Chem. Soc. A 1969, 2372-2382. (b) Blake, C., C. F.; Small, R. W. H. Acta Crystallogr. 1972, B28, 2201-2206. (c) Cobbledick, R. E.; Small, R. W. H. Acta Crystallogr. 1972, B28, 2893-2896. (d) Berkovitch-Yellin, Z.; Leiserowitz, L. J. Am. Chem. Soc. 1980, 102, 7677-7690. (e) Leiserowitz, L.; Hagler, A. T. Proc. R. Soc. London 1983, A388, 133-175. (f) Aakeröy, C. B.; Beatty, A. M. Chem. Commun. 1998, 1067-1068. (g) Edgar, R.; Schultz, T. M.; Rasmussen, F. B.; Feidenhans' I.R. ; Leiserowitz, L. J. Am. Chem. Soc. 1999, 121, 632-637. (h) Kobko, N.; Paraskevas, L.; del Rio, E.; Dannenberg, J. J. J. Am. Chem. Soc. 2001, 123, 4348-4349.
54. For hydrogen-bonding motifs of the secondary amide group, see: (a) Leiserowitz, L.; Tuval, M. Acta Crystallogr. 1978, B34, 1230-1247. (b) Weinstein, S.; Leiserowitz, L.; Gil-Av, E. J. Am. Chem. Soc. 1980, 102, 2768-2772. (c) Garcia-Tellado, F.; Geib, S. J.; Goswami, S.; Hamilton, A. D. J. Am. Chem. Soc. 1991, 113, 9265-9269. (d) Reference 10a. (e) Fan, E.; Yang, J.; Geib, S. J.; Stoner, T. C.; Hopkins, M. D.; Hamilton, A. D. J. Chem. Soc., Chem. Commun. 1995, 1251-1252. (f) Lewis, F. D.; Yang, J.-S.; Stern, C. L. J. Am. Chem. Soc. 1996, 118, 12029-12037. (g) Lightfoot, M. P.; Mair, F. S.; Pritchard, R. G.; Warren, J. E. Chem. Commun. 1999, 1945-1946. (h) Nguyen, T. L.; Fowler, F. W.; Lauher, J. W. J. Am. Chem. Soc. 2001, 123, 11057-11064.
55. For hydrogen-bonding motifs of the secondary amide group, see: (a) Leiserowitz, L.; Tuval, M. Acta Crystallogr. 1978, B34, 1230-1247. (b) Weinstein, S.; Leiserowitz, L.; Gil-Av, E. J. Am. Chem. Soc. 1980, 102, 2768-2772. (c) Garcia-Tellado, F.; Geib, S. J.; Goswami, S.; Hamilton, A. D. J. Am. Chem. Soc. 1991, 113, 9265-9269. (d) Reference 10a. (e) Fan, E.; Yang, J.; Geib, S. J.; Stoner, T. C.; Hopkins, M. D.; Hamilton, A. D. J. Chem. Soc., Chem. Commun. 1995, 1251-1252. (f) Lewis, F. D.; Yang, J.-S.; Stern, C. L. J. Am. Chem. Soc. 1996, 118, 12029-12037. (g) Lightfoot, M. P.; Mair, F. S.; Pritchard, R. G.; Warren, J. E. Chem. Commun. 1999, 1945-1946. (h) Nguyen, T. L.; Fowler, F. W.; Lauher, J. W. J. Am. Chem. Soc. 2001, 123, 11057-11064.
56. For hydrogen-bonding motifs of the secondary amide group, see: (a) Leiserowitz, L.; Tuval, M. Acta Crystallogr. 1978, B34, 1230-1247. (b) Weinstein, S.; Leiserowitz, L.; Gil-Av, E. J. Am. Chem. Soc. 1980, 102, 2768-2772. (c) Garcia-Tellado, F.; Geib, S. J.; Goswami, S.; Hamilton, A. D. J. Am. Chem. Soc. 1991, 113, 9265-9269. (d) Reference 10a. (e) Fan, E.; Yang, J.; Geib, S. J.; Stoner, T. C.; Hopkins, M. D.; Hamilton, A. D. J. Chem. Soc., Chem. Commun. 1995, 1251-1252. (f) Lewis, F. D.; Yang, J.-S.; Stern, C. L. J. Am. Chem. Soc. 1996, 118, 12029-12037. (g) Lightfoot, M. P.; Mair, F. S.; Pritchard, R. G.; Warren, J. E. Chem. Commun. 1999, 1945-1946. (h) Nguyen, T. L.; Fowler, F. W.; Lauher, J. W. J. Am. Chem. Soc. 2001, 123, 11057-11064.
57. For hydrogen-bonding motifs of the secondary amide group, see: (a) Leiserowitz, L.; Tuval, M. Acta Crystallogr. 1978, B34, 1230-1247. (b) Weinstein, S.; Leiserowitz, L.; Gil-Av, E. J. Am. Chem. Soc. 1980, 102, 2768-2772. (c) Garcia-Tellado, F.; Geib, S. J.; Goswami, S.; Hamilton, A. D. J. Am. Chem. Soc. 1991, 113, 9265-9269. (d) Reference 10a. (e) Fan, E.; Yang, J.; Geib, S. J.; Stoner, T. C.; Hopkins, M. D.; Hamilton, A. D. J. Chem. Soc., Chem. Commun. 1995, 1251-1252. (f) Lewis, F. D.; Yang, J.-S.; Stern, C. L. J. Am. Chem. Soc. 1996, 118, 12029-12037. (g) Lightfoot, M. P.; Mair, F. S.; Pritchard, R. G.; Warren, J. E. Chem. Commun. 1999, 1945-1946. (h) Nguyen, T. L.; Fowler, F. W.; Lauher, J. W. J. Am. Chem. Soc. 2001, 123, 11057-11064.
58. For hydrogen-bonding motifs of the secondary amide group, see: (a) Leiserowitz, L.; Tuval, M. Acta Crystallogr. 1978, B34, 1230-1247. (b) Weinstein, S.; Leiserowitz, L.; Gil-Av, E. J. Am. Chem. Soc. 1980, 102, 2768-2772. (c) Garcia-Tellado, F.; Geib, S. J.; Goswami, S.; Hamilton, A. D. J. Am. Chem. Soc. 1991, 113, 9265-9269. (d) Reference 10a. (e) Fan, E.; Yang, J.; Geib, S. J.; Stoner, T. C.; Hopkins, M. D.; Hamilton, A. D. J. Chem. Soc., Chem. Commun. 1995, 1251-1252. (f) Lewis, F. D.; Yang, J.-S.; Stern, C. L. J. Am. Chem. Soc. 1996, 118, 12029-12037. (g) Lightfoot, M. P.; Mair, F. S.; Pritchard, R. G.; Warren, J. E. Chem. Commun. 1999, 1945-1946. (h) Nguyen, T. L.; Fowler, F. W.; Lauher, J. W. J. Am. Chem. Soc. 2001, 123, 11057-11064.
59. For hydrogen-bonding motifs of the secondary amide group, see: (a) Leiserowitz, L.; Tuval, M. Acta Crystallogr. 1978, B34, 1230-1247. (b) Weinstein, S.; Leiserowitz, L.; Gil-Av, E. J. Am. Chem. Soc. 1980, 102, 2768-2772. (c) Garcia-Tellado, F.; Geib, S. J.; Goswami, S.; Hamilton, A. D. J. Am. Chem. Soc. 1991, 113, 9265-9269. (d) Reference 10a. (e) Fan, E.; Yang, J.; Geib, S. J.; Stoner, T. C.; Hopkins, M. D.; Hamilton, A. D. J. Chem. Soc., Chem. Commun. 1995, 1251-1252. (f) Lewis, F. D.; Yang, J.-S.; Stern, C. L. J. Am. Chem. Soc. 1996, 118, 12029-12037. (g) Lightfoot, M. P.; Mair, F. S.; Pritchard, R. G.; Warren, J. E. Chem. Commun. 1999, 1945-1946. (h) Nguyen, T. L.; Fowler, F. W.; Lauher, J. W. J. Am. Chem. Soc. 2001, 123, 11057-11064.
60. For hydrogen-bonding motifs of the secondary amide group, see: (a) Leiserowitz, L.; Tuval, M. Acta Crystallogr. 1978, B34, 1230-1247. (b) Weinstein, S.; Leiserowitz, L.; Gil-Av, E. J. Am. Chem. Soc. 1980, 102, 2768-2772. (c) Garcia-Tellado, F.; Geib, S. J.; Goswami, S.; Hamilton, A. D. J. Am. Chem. Soc. 1991, 113, 9265-9269. (d) Reference 10a. (e) Fan, E.; Yang, J.; Geib, S. J.; Stoner, T. C.; Hopkins, M. D.; Hamilton, A. D. J. Chem. Soc., Chem. Commun. 1995, 1251-1252. (f) Lewis, F. D.; Yang, J.-S.; Stern, C. L. J. Am. Chem. Soc. 1996, 118, 12029-12037. (g) Lightfoot, M. P.; Mair, F. S.; Pritchard, R. G.; Warren, J. E. Chem. Commun. 1999, 1945-1946. (h) Nguyen, T. L.; Fowler, F. W.; Lauher, J. W. J. Am. Chem. Soc. 2001, 123, 11057-11064.
61. For hydrogen-bonding motifs of the secondary amide group, see: (a) Leiserowitz, L.; Tuval, M. Acta Crystallogr. 1978, B34, 1230-1247. (b) Weinstein, S.; Leiserowitz, L.; Gil-Av, E. J. Am. Chem. Soc. 1980, 102, 2768-2772. (c) Garcia-Tellado, F.; Geib, S. J.; Goswami, S.; Hamilton, A. D. J. Am. Chem. Soc. 1991, 113, 9265-9269. (d) Reference 10a. (e) Fan, E.; Yang, J.; Geib, S. J.; Stoner, T. C.; Hopkins, M. D.; Hamilton, A. D. J. Chem. Soc., Chem. Commun. 1995, 1251-1252. (f) Lewis, F. D.; Yang, J.-S.; Stern, C. L. J. Am. Chem. Soc. 1996, 118, 12029-12037. (g) Lightfoot, M. P.; Mair, F. S.; Pritchard, R. G.; Warren, J. E. Chem. Commun. 1999, 1945-1946. (h) Nguyen, T. L.; Fowler, F. W.; Lauher, J. W. J. Am. Chem. Soc. 2001, 123, 11057-11064.
62. For hydrogen-bonding motifs of the carboxylic acid group, see: (a) Leiserowitz, L. Acta Crystallogr. 1976, B32, 775-802. (b) Berkovitch-Yellin, Z.; Leiserowitz, L. J. Am. Chem. Soc. 1982, 104, 4052-4064. (c) Reference 9. (d) Kuduva, S. S.; Craig, D. C.; Nangia, A.; Desiraju, G. R. J. Am. Chem. Soc. 1999, 121, 1936-1944. (e) Moorthy, J. N.; Natarajan, R.; Mal, P.; Venugopalan, P. J. Am. Chem. Soc. 2002, 124, 6530-6531.
63. For hydrogen-bonding motifs of the carboxylic acid group, see: (a) Leiserowitz, L. Acta Crystallogr. 1976, B32, 775-802. (b) Berkovitch-Yellin, Z.; Leiserowitz, L. J. Am. Chem. Soc. 1982, 104, 4052-4064. (c) Reference 9. (d) Kuduva, S. S.; Craig, D. C.; Nangia, A.; Desiraju, G. R. J. Am. Chem. Soc. 1999, 121, 1936-1944. (e) Moorthy, J. N.; Natarajan, R.; Mal, P.; Venugopalan, P. J. Am. Chem. Soc. 2002, 124, 6530-6531.
64. For hydrogen-bonding motifs of the carboxylic acid group, see: (a) Leiserowitz, L. Acta Crystallogr. 1976, B32, 775-802. (b) Berkovitch-Yellin, Z.; Leiserowitz, L. J. Am. Chem. Soc. 1982, 104, 4052-4064. (c) Reference 9. (d) Kuduva, S. S.; Craig, D. C.; Nangia, A.; Desiraju, G. R. J. Am. Chem. Soc. 1999, 121, 1936-1944. (e) Moorthy, J. N.; Natarajan, R.; Mal, P.; Venugopalan, P. J. Am. Chem. Soc. 2002, 124, 6530-6531.
65. For hydrogen-bonding motifs of the carboxylic acid group, see: (a) Leiserowitz, L. Acta Crystallogr. 1976, B32, 775-802. (b) Berkovitch-Yellin, Z.; Leiserowitz, L. J. Am. Chem. Soc. 1982, 104, 4052-4064. (c) Reference 9. (d) Kuduva, S. S.; Craig, D. C.; Nangia, A.; Desiraju, G. R. J. Am. Chem. Soc. 1999, 121, 1936-1944. (e) Moorthy, J. N.; Natarajan, R.; Mal, P.; Venugopalan, P. J. Am. Chem. Soc. 2002, 124, 6530-6531.
66. For hydrogen-bonding motifs of the carboxylic acid group, see: (a) Leiserowitz, L. Acta Crystallogr. 1976, B32, 775-802. (b) Berkovitch-Yellin, Z.; Leiserowitz, L. J. Am. Chem. Soc. 1982, 104, 4052-4064. (c) Reference 9. (d) Kuduva, S. S.; Craig, D. C.; Nangia, A.; Desiraju, G. R. J. Am. Chem. Soc. 1999, 121, 1936-1944. (e) Moorthy, J. N.; Natarajan, R.; Mal, P.; Venugopalan, P. J. Am. Chem. Soc. 2002, 124, 6530-6531.
67. For supramolecular (architectural) isomerism in hydrogen-bonded networks, see: (a) Miyata, M.; Shibakami, M.; Chirachanchai, S.; Takemoto, K.; Kasai, N.; Miki, K. Nature 1990, 343, 446-447.(b) MacGillivray, L. R.; Reid, J. L.; Ripmeester, J. A. Chem. Commun. 2001, 1034-1035. (c) Reference 11b. (d) Reference 17f. (e) Horner, M. J.; Holman, K. T.; Ward, M. D. Angew. Chem., Int. Ed. 2001, 40, 4045-4048.
68. For supramolecular (architectural) isomerism in hydrogen-bonded networks, see: (a) Miyata, M.; Shibakami, M.; Chirachanchai, S.; Takemoto, K.; Kasai, N.; Miki, K. Nature 1990, 343, 446-447.(b) MacGillivray, L. R.; Reid, J. L.; Ripmeester, J. A. Chem. Commun. 2001, 1034-1035. (c) Reference 11b. (d) Reference 17f. (e) Horner, M. J.; Holman, K. T.; Ward, M. D. Angew. Chem., Int. Ed. 2001, 40, 4045-4048.
69. For supramolecular (architectural) isomerism in hydrogen-bonded networks, see: (a) Miyata, M.; Shibakami, M.; Chirachanchai, S.; Takemoto, K.; Kasai, N.; Miki, K. Nature 1990, 343, 446-447.(b) MacGillivray, L. R.; Reid, J. L.; Ripmeester, J. A. Chem. Commun. 2001, 1034-1035. (c) Reference 11b. (d) Reference 17f. (e) Horner, M. J.; Holman, K. T.; Ward, M. D. Angew. Chem., Int. Ed. 2001, 40, 4045-4048.
70. For supramolecular (architectural) isomerism in hydrogen-bonded networks, see: (a) Miyata, M.; Shibakami, M.; Chirachanchai, S.; Takemoto, K.; Kasai, N.; Miki, K. Nature 1990, 343, 446-447.(b) MacGillivray, L. R.; Reid, J. L.; Ripmeester, J. A. Chem. Commun. 2001, 1034-1035. (c) Reference 11b. (d) Reference 17f. (e) Horner, M. J.; Holman, K. T.; Ward, M. D. Angew. Chem., Int. Ed. 2001, 40, 4045-4048.
71. For supramolecular (architectural) isomerism in hydrogen-bonded networks, see: (a) Miyata, M.; Shibakami, M.; Chirachanchai, S.; Takemoto, K.; Kasai, N.; Miki, K. Nature 1990, 343, 446-447.(b) MacGillivray, L. R.; Reid, J. L.; Ripmeester, J. A. Chem. Commun. 2001, 1034-1035. (c) Reference 11b. (d) Reference 17f. (e) Horner, M. J.; Holman, K. T.; Ward, M. D. Angew. Chem., Int. Ed. 2001, 40, 4045-4048.
72. For supramolecular (architectural) isomerism in metal coordination networks, see: (a) Hennigar, T. L.; MacQuarrie, D. C.; Losier, P.; Rogers, R. D.; Zaworotko, M. J. Angew. Chem., Int. Ed. 1997, 36, 972-973. (b) Kasai, K.; Aoyagi, M.; Fujita, M. J. Am. Chem. Soc. 2000, 122, 2140-2141. (c) Bourne, S. A.; Lu, J.; Moulton, B.; Zaworotko, M. J. Chem. Commun. 2001, 861-862.
73. For supramolecular (architectural) isomerism in metal coordination networks, see: (a) Hennigar, T. L.; MacQuarrie, D. C.; Losier, P.; Rogers, R. D.; Zaworotko, M. J. Angew. Chem., Int. Ed. 1997, 36, 972-973. (b) Kasai, K.; Aoyagi, M.; Fujita, M. J. Am. Chem. Soc. 2000, 122, 2140-2141. (c) Bourne, S. A.; Lu, J.; Moulton, B.; Zaworotko, M. J. Chem. Commun. 2001, 861-862.
74. For supramolecular (architectural) isomerism in metal coordination networks, see: (a) Hennigar, T. L.; MacQuarrie, D. C.; Losier, P.; Rogers, R. D.; Zaworotko, M. J. Angew. Chem., Int. Ed. 1997, 36, 972-973. (b) Kasai, K.; Aoyagi, M.; Fujita, M. J. Am. Chem. Soc. 2000, 122, 2140-2141. (c) Bourne, S. A.; Lu, J.; Moulton, B.; Zaworotko, M. J. Chem. Commun. 2001, 861-862.
75. For correlation between donor and acceptor abilities in stronger and weaker hydrogen bonds, see: (a) Etter, M. C.; Panunto, T. W. J. Am. Chem. Soc. 1988, 110, 5896-5897. (b) Reference 2b. (c) Reference 20d. (d) Aakeröy, C. B.; Beatty, A. M.; Helfrich, B. A. Angew. Chem., Int. Ed. 2001, 40, 3240-3242.
76. For correlation between donor and acceptor abilities in stronger and weaker hydrogen bonds, see: (a) Etter, M. C.; Panunto, T. W. J. Am. Chem. Soc. 1988, 110, 5896-5897. (b) Reference 2b. (c) Reference 20d. (d) Aakeröy, C. B.; Beatty, A. M.; Helfrich, B. A. Angew. Chem., Int. Ed. 2001, 40, 3240-3242.
77. For correlation between donor and acceptor abilities in stronger and weaker hydrogen bonds, see: (a) Etter, M. C.; Panunto, T. W. J. Am. Chem. Soc. 1988, 110, 5896-5897. (b) Reference 2b. (c) Reference 20d. (d) Aakeröy, C. B.; Beatty, A. M.; Helfrich, B. A. Angew. Chem., Int. Ed. 2001, 40, 3240-3242.
78. For correlation between donor and acceptor abilities in stronger and weaker hydrogen bonds, see: (a) Etter, M. C.; Panunto, T. W. J. Am. Chem. Soc. 1988, 110, 5896-5897. (b) Reference 2b. (c) Reference 20d. (d) Aakeröy, C. B.; Beatty, A. M.; Helfrich, B. A. Angew. Chem., Int. Ed. 2001, 40, 3240-3242.
79. Burdett, K. A. Synthesis 1991, 441-442.
80. 2O and obtain single crystals suitable for the X-ray diffraction analysis.
81. For helical network motif of primary amides: (a) Long, R. E.; Maddox, H.; Trueblood, K. N. Acta Crystallogr. 1969, B25, 2083-2094. (b) References 18d,e and references therein.
82. For helical network motif of primary amides: (a) Long, R. E.; Maddox, H.; Trueblood, K. N. Acta Crystallogr. 1969, B25, 2083-2094. (b) References 18d,e and references therein.
83. This work.
84. h value was calculated with Hyperchem Pro 6.0 as the software and QSAR properties as a module.
85. The hydrogen bond of the n-PrO11H with the N5-H anti proton of amide group 5 is very weak (the N5⋯O11 distance is 3.26 Å) because the n-PrO11H hydrogen bonds tightly to the n-PrO9H with an O9⋯O11 distance of 2.68 Å (Figure 8d). The interatomic distance of O1⋯O12 (3.43 Å) is too long to make a hydrogen bond, because the n-PrO12H group hydrogen-bonds to both the n-PrO10H and the n-PrO11H groups with O⋯O distances of 3.04 and 3.18 Å, respectively (Figure 8c,d). Thus, there is a hydrogen-bonding chain of O10⋯O12⋯O11⋯O9 among the included guest molecules in the channel of 1.
86. For the helical network motif of secondary amides using the N-H anti proton, see: (a) Geib, S. J.; Vicent, C.; Fan, E.; Hamilton, A. D. Angew. Chem., Int. Ed. Engl. 1993, 32, 119-121. (b) Reference 19g.
87. For the helical network motif of secondary amides using the N-H anti proton, see: (a) Geib, S. J.; Vicent, C.; Fan, E.; Hamilton, A. D. Angew. Chem., Int. Ed. Engl. 1993, 32, 119-121. (b) Reference 19g.
88. For other helical hydrogen-bonded network motifs of hosts without chiral centers, see: (a) Hollingsworth, M. D.; Harris, K. D. M. In Comprehensive Supramolecular Chemistry, Solid-State Supramolecular Chemistry: Crystal Engineering; MacNicol, D. D., Toda, F., Bishop, R., Eds.: Pergamon: New York, 1996; Vol. 6, pp 177-237. (b) Allen, W. E.; Fowler, C. J.; Lynch, V. M.; Sessler, J. L. Chem. Eur. J. 2001, 7, 721-729.
89. For other helical hydrogen-bonded network motifs of hosts without chiral centers, see: (a) Hollingsworth, M. D.; Harris, K. D. M. In Comprehensive Supramolecular Chemistry, Solid-State Supramolecular Chemistry: Crystal Engineering; MacNicol, D. D., Toda, F., Bishop, R., Eds.: Pergamon: New York, 1996; Vol. 6, pp 177-237. (b) Allen, W. E.; Fowler, C. J.; Lynch, V. M.; Sessler, J. L. Chem. Eur. J. 2001, 7, 721-729.
90. For other helical hydrogen-bonded network motifs of hosts with chiral centers, see: (a) Ung, A. T.; Gizachew, D.; Bishop, R.; Scudder, M. L.; Dance, I. G.; Craig, D. C. J. Am. Chem. Soc. 1995, 117, 8745-8756. (b) Hirschberg, J. H. K. K.; Brunsveld, L.; Ramzi, A.; Vekemans, J. A. J. M.; Sijbesma, R. P.; Meijer, E. W. Nature 2000, 407, 167-170. (c) Moriuchi, T.; Nomoto, A.; Yoshida, K.; Ogawa, A.; Hirao, T. J. Am. Chem. Soc. 2001, 123, 68-75. (d) Radhakrishnan, T. P.; Gangopadhyay, P. Angew. Chem., Int. Ed. 2001, 40, 2451-2455. (e) Custelcean, R.; Ward, M. D. Angew. Chem., Int. Ed. 2002, 41, 1724-1728.
91. For other helical hydrogen-bonded network motifs of hosts with chiral centers, see: (a) Ung, A. T.; Gizachew, D.; Bishop, R.; Scudder, M. L.; Dance, I. G.; Craig, D. C. J. Am. Chem. Soc. 1995, 117, 8745-8756. (b) Hirschberg, J. H. K. K.; Brunsveld, L.; Ramzi, A.; Vekemans, J. A. J. M.; Sijbesma, R. P.; Meijer, E. W. Nature 2000, 407, 167-170. (c) Moriuchi, T.; Nomoto, A.; Yoshida, K.; Ogawa, A.; Hirao, T. J. Am. Chem. Soc. 2001, 123, 68-75. (d) Radhakrishnan, T. P.; Gangopadhyay, P. Angew. Chem., Int. Ed. 2001, 40, 2451-2455. (e) Custelcean, R.; Ward, M. D. Angew. Chem., Int. Ed. 2002, 41, 1724-1728.
92. For other helical hydrogen-bonded network motifs of hosts with chiral centers, see: (a) Ung, A. T.; Gizachew, D.; Bishop, R.; Scudder, M. L.; Dance, I. G.; Craig, D. C. J. Am. Chem. Soc. 1995, 117, 8745-8756. (b) Hirschberg, J. H. K. K.; Brunsveld, L.; Ramzi, A.; Vekemans, J. A. J. M.; Sijbesma, R. P.; Meijer, E. W. Nature 2000, 407, 167-170. (c) Moriuchi, T.; Nomoto, A.; Yoshida, K.; Ogawa, A.; Hirao, T. J. Am. Chem. Soc. 2001, 123, 68-75. (d) Radhakrishnan, T. P.; Gangopadhyay, P. Angew. Chem., Int. Ed. 2001, 40, 2451-2455. (e) Custelcean, R.; Ward, M. D. Angew. Chem., Int. Ed. 2002, 41, 1724-1728.
93. For other helical hydrogen-bonded network motifs of hosts with chiral centers, see: (a) Ung, A. T.; Gizachew, D.; Bishop, R.; Scudder, M. L.; Dance, I. G.; Craig, D. C. J. Am. Chem. Soc. 1995, 117, 8745-8756. (b) Hirschberg, J. H. K. K.; Brunsveld, L.; Ramzi, A.; Vekemans, J. A. J. M.; Sijbesma, R. P.; Meijer, E. W. Nature 2000, 407, 167-170. (c) Moriuchi, T.; Nomoto, A.; Yoshida, K.; Ogawa, A.; Hirao, T. J. Am. Chem. Soc. 2001, 123, 68-75. (d) Radhakrishnan, T. P.; Gangopadhyay, P. Angew. Chem., Int. Ed. 2001, 40, 2451-2455. (e) Custelcean, R.; Ward, M. D. Angew. Chem., Int. Ed. 2002, 41, 1724-1728.
94. For other helical hydrogen-bonded network motifs of hosts with chiral centers, see: (a) Ung, A. T.; Gizachew, D.; Bishop, R.; Scudder, M. L.; Dance, I. G.; Craig, D. C. J. Am. Chem. Soc. 1995, 117, 8745-8756. (b) Hirschberg, J. H. K. K.; Brunsveld, L.; Ramzi, A.; Vekemans, J. A. J. M.; Sijbesma, R. P.; Meijer, E. W. Nature 2000, 407, 167-170. (c) Moriuchi, T.; Nomoto, A.; Yoshida, K.; Ogawa, A.; Hirao, T. J. Am. Chem. Soc. 2001, 123, 68-75. (d) Radhakrishnan, T. P.; Gangopadhyay, P. Angew. Chem., Int. Ed. 2001, 40, 2451-2455. (e) Custelcean, R.; Ward, M. D. Angew. Chem., Int. Ed. 2002, 41, 1724-1728.
95. Abraham, M. H.; Platts, J. A. J. Org. Chem. 2001, 66, 3484-3491 and references therein.
96. 33
97. Kamlet, M. J.; Abboud, J.-L. M.; Abraham, M. H.; Taft, R. W. J. Org. Chem. 1983, 48, 2877-2887.
98. (a) Jorgensen, W. L.; Severance, D. L. J. Am. Chem. Soc. 1990, 112, 4768-4774.
99. (b) Fujita, M.; Fujita, N.; Ogura, K.; Yamaguchi, K. Nature 1999, 400, 52-55.
100. A reviewer suggested that high pressure under hydrothermal conditions would also play an important role in the network formation of type C.
101. Sheldrick, G. M. SHELXS-97; University of Göttingen, Göttingen, Germany, 1997.
102. Altomare, A.; Cascarano, M.; Giacovazzo, C.; Guagliardi, A. SIR92. J. Appl. Crystallogr. 1993, 26, 343.
103. TeXsan for Windows, Crystal Structure Analysis Package; Molecular Structure Corp., The Woodlands, TX, 1997.