Organic ammonium carboxylates as supramolecular building blocks: The role of ionic hydrogen bonding

Synlett

Volumn , Issue 15, 2006, Pages 2364-2374

  Sada, Kazuki ^a   Tani, Takahiro ^a   Shinkai, Seiji ^a  

^a KYUSHU UNIVERSITY   (Japan)

Author keywords

Ammonium carboxylates; Crystal engineering; Ionic hydrogen bonds; Organogels; Topochemical polymerization

Indexed keywords

ACETIC ACID DERIVATIVE; AMIDINE; ANION; CARBOXYLIC ACID; CARBOXYLIC ACID DERIVATIVE; CATION; GUANIDINE; ION; LYSINE; METHYLAMMONIUM; OXYGEN; PROTEIN DERIVATIVE; QUATERNARY AMMONIUM DERIVATIVE; SODIUM CHLORIDE; SULFONIC ACID DERIVATIVE; TERT BUTYLAMMONIUM TRIPHENYLACETATE; THIOUREA; UNCLASSIFIED DRUG; UREA;

ATOM; CHEMICAL BOND; CHEMICAL STRUCTURE; CLUSTER ANALYSIS; CRYSTAL STRUCTURE; CRYSTALLIZATION; ELECTRICITY; GAS; GEL; HISTOGRAM; HYDROGEN BOND; REVIEW; SUPRAMOLECULAR CHEMISTRY;

EID: 33749344101     PISSN: 09365214     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-2006-951469     Document Type: Review

References (93)

1. Lehn, J.-M. Supramolecular Chemistry - Concept and Perspectives; VCH: Weinheim, 1995.
2. Comprehensive Supramolecular Chemistry; Atwood, J. L.; Davies, J. E. D.; MacNicol, D. D.; Vögtle, F., Eds.; Pergamon: Oxford, 1996.
3. Barlow, D. J.; Thornton, J. M. J. Mol. Biol. 1983, 168, 867.
4. Perutz, M. F. Science (Washington, D. C.) 1989, 201, 1187.
5. Meot-Ner, M. Chem. Rev. 2005, 105, 213.
6. Schmidtchen, F. P. Chem. Rev. 1997, 97, 1609.
7. Schug, K. A.; Linder, W. Chem. Rev. 2005, 105, 67.
8. (a) Felix, O.; Hosseini, M. W.; Cian, D. A. Solid State Sci. 2001, 3, 789.
9. (b) Hosseini, M. W. Coord. Chem. Rev. 2003, 240, 157.
10. (c) Hosseini, M. W. Acc. Chem. Res. 2005, 38, 313.
11. Fitmaurice, R. J.; Kyne, G. M.; Douheret, D.; Kilburn, J. D. J. Chem. Soc., Perkin Trans. 1 2002, 841.
12. Subramanian, S.; Zaworotko, M. J. Coord. Chem. Rev. 1994, 137, 357.
13. (a) Russell, V. A.; Etter, M. C.; Ward, M. D. Chem. Mater. 1994, 6, 1206.
14. (b) Holman, K. T.; Pivovar, A. M.; Swift, J. A.; Ward, M. D. Acc. Chem. Res. 2001, 34, 107.
15. Prins, J.; Reinhoudt, D. N.; Timmerman, P. L. Angew. Chem. Int. Ed. 2001, 40, 2382.
16. Molecular Recognition: Receptors for Cationic Guests, In Comprehensive Supramolecular Chemistry, Vol. 1; Gokel, G. W., Ed.; Pergamon: Oxford, 1996.
17. Jorgensen, W. L.; Gao, J. J. Phys. Chem. 1986, 90, 2174.
18. A typical example for a 1:1 complex of urea and carboxylate anion in the crystalline state, see: Li, Q.; Mak, T. C. W. J. Inclusion Phenom. Macrocyclic Chem. 1999, 35, 621.
19. For example, see: Gallivan, J. P.; Dougherty, D. A. J. Am. Chem. Soc. 2000, 122, 870.
20. (a) Dougherty, D. A. Science (Washington, D. C.) 1996, 271, 5246.
21. (b) Ma, J. C.; Dougherty, D. A. Chem. Rev. 1997, 97, 1303.
22. Desiraju, G. R. Crystal Engineering: The Design of Organic Solids; Elsevier: Amsterdam, 1989.
23. Solid-State Supramolecular Chemistry: Crystal Engineering, In Comprehensive Supramolecular Chemistry, Vol. 6; MacNicol, D. D.; Toda, F.; Bishop, R., Eds.; Pergamon: Oxford, 1996.
24. (a) Hydrogen Bonding in Biology and Chemistry, Jeffery, G. A.; Saenger, W., Eds.; Springer-Verlag: Berlin, 1993.
25. (b) Introduction to Hydrogen Bonding; Jeffery G. A., Wiley: Chichester, 1997.
26. (a) Aakeröy, C. B.; Seddon, K. R. Chem. Soc. Rev. 1993, 22, 397.
27. (b) Aakeröy, C. B.; Beatty, A. M. Aust. J. Chem. 2001, 54, 409.
28. (c) Aakeröy, C. B.; Hughes, D. P.; McCabe, A. M.; Nieuwenhuyzen, M. Supramol. Chem. 1998, 9, 127.
29. MacDonald, J. C.; Whiteside, G. M. Chem. Rev. 1994, 94, 2383.
30. Burrows, A. D. Struct. Bonding (Berlin) 2004, 108, 55.
31. Ferretti, V.; Bertolasi, V.; Pretto, L. New J. Chem. 2004, 28, 646.
32. Krische, M. J.; Lehn, J.-M. Struct. Bonding (Berlin) 2000, 96, 3.
33. Melendez, R. E.; Hamilton, A. D. Top. Curr. Chem. 1998, 198, 97.
34. Etter, M. C. Acc. Chem. Res. 1990, 23, 120.
35. Allen, F. H.; Kennard, O. Chem. Des. Autom. News 1993, 8, 3137; CSD version 5, 26 Nov. 2004.
36. Udachin, K. A.; Ripmester, J. A. Angew. Chem. Int. Ed. 1999, 38, 1983.
37. Viertorinen, M.; Valkonen, J.; Pitkanen, I.; Mathlouthi, M.; Numi, J. J. Mol. Struct. 1999, 477, 23.
38. Mallinson, P. R.; Smith, G. T.; Wilson, C. C.; Grech, E.; Wozniak, K. J. Am. Chem. Soc. 2003, 125, 4259.
39. (a) Melendez, R. E.; Sharma, C. V. K.; Zaworotko, M. J.; Bauer, C.; Rogers, R. D. Angew. Chem., Int. Ed. Engl. 1996, 35, 2213.
40. (b) Biradha, K.; Zaworotko, M. J. J. Am. Chem. Soc. 1998, 120, 6431.
41. (c) Biradha, K.; Dennis, D.; MacKinnon, V. A. K.; Sharma, C. V.; Zaworotko, M. J. J. Am. Chem. Soc. 1998, 120, 11894.
42. (d) Moulton, B.; Zaworotko, M. J. Chem. Rev. 2001, 101, 1629.
43. (a) Dastidar, P.; Ballabh, A.; Trivedi, D. R. Cryst. Growth Des. 2005, 5, 1545.
44. (b) Ballabh, A.; Trivedi, D. R.; Suresh, E. CrystEngComm 2002, 24, 135.
45. Kinbara, K.; Hashimoto, Y.; Sukegawa, M.; Noriha, H.; Saigo, K. J. Am. Chem. Soc. 1996, 118, 3441.
46. Matsumoto, A.; Odani, T.; Chikada, M.; Sada, K.; Miyata, M. J. Am. Chem. Soc. 1999, 121, 11122.
47. (a) Terech, P.; Weiss, R. G. Chem. Rev. 1997, 97, 3133.
48. (b) Gronwald, O.; Snip, E.; Shinkai, S. Curr. Opin. Colloid Interface Sci. 2002, 7, 148.
49. (c) Estroff, L. A.; Hamilton, A. D. Chem. Rev. 2004, 104, 1201.
50. (a) Oda, R.; Huc, I.; Candau, S. J. Chem. Commun. 1997, 2105.
51. (b) Oda, R.; Huc, I.; Candau, S. J. Angew. Chem. Int. Ed. 1998, 37, 2689.
52. (a) Nakano, K.; Hishikawa, Y.; Sada, K.; Miyata, M.; Hanabusa, K. Chem. Lett. 2000, 1170.
53. (b) Dastidar, P.; Okabe, S.; Nakano, K.; Iida, K.; Miyata, M.; Tohnai, N.; Shibayama, M. Chem. Mater. 2005, 17, 741.
54. (a) Hirst, A. R.; Smith, D. K. Org. Biomol. Chem. 2004, 2965.
55. (b) Partridge, K. S.; Smith, D. K.; Dykes, G. M.; McGrail, P. T. Chem. Commun. 2001, 319.
56. (c) Hirst, A. R.; Smith, D. K.; Feiters, M. C.; Geurts, H. P. M. Chem. Eur. J. 2004, 10, 5901.
57. (d) Hirst, A. R.; Smith, D. K.; Feiters, M. C.; Geurts, H. P. M. Langmuir 2004, 20, 7070.
58. (e) Hirst, A. R.; Smith, D. K. Langmuir 2004, 20, 10851.
59. (f) Huang, B.; Hirst, A. R.; Smith, D. K.; Castelletto, V.; Hamley, I. W. J. Am. Chem. Soc. 2005, 127, 7130.
60. (a) Ballabh, A.; Trivedi, D. R.; Dastidar, P. Chem. Mater. 2003, 15, 2136.
61. (b) Trivedi, D. R.; Ballabh, A.; Dastidar, P. Chem. Mater. 2003, 15, 3971.
62. (c) Trivedi, D. R.; Ballabh, A.; Dastidar, P.; Ganguly, B. Chem. Eur. J. 2004, 10, 5311.
63. (a) Ayabe, M.; Kishida, T.; Fujita, N.; Sada, K.; Shinkai, S. Org. Biomol. Chem. 2003, 1, 2744.
64. (b) Tani, T.; Sada, K.; Ayabe, M.; Iwashita, Y.; Kishida, T.; Shirakawa, M.; Fujita, N.; Shinkai, S. Collect. Czech. Chem. Commun. 2004, 69, 1292.
65. (a) Kolthoff, I. M. Anal. Chem. 1974, 46, 1992.
66. (b) Brunckenstein, S.; Untereker, D. F. J. Am. Chem. Soc. 1969, 91, 5741.
67. (c) Brunckenstein, S.; Saito, A. J. Am. Chem. Soc. 1965, 87, 698.
68. (d) Zingg, S. P.; Arnett, E. M.; McPhail, A. T.; Bothner-By, A. A.; Gilkerson, W. R. J. Am. Chem. Soc. 1988, 110, 1565.
69. (e) DeTar, D. F.; Novak, R. W. J. Am. Chem. Soc. 1970, 92, 1361.
70. (a) Barrow, G. M.; Yerger, E. A. J. Am. Chem. Soc. 1954, 76, 5211.
71. (b) Barrow, G. M.; Yerger, E. A. J. Am. Chem. Soc. 1955, 77, 6206.
72. (c) Barrow, G. M. J. Am. Chem. Soc. 1958, 80, 86.
73. Sada, K.; Watanabe, T.; Miyamoto, J.; Fukuka, T.; Tohnai, N.; Miyata, M.; Kitayama, T.; Meahara, K.; Ute, K. Chem. Lett. 2004, 33, 160.
74. Yamaguchi, K. J. Mass Spectrom. 2003, 38, 473.
75. (a) Horovitz, A.; Serrano, L.; Avron, B.; Bycroft, M.; Fersht, A. R. J. Mol. Biol. 1990, 216, 1031.
76. (b) Fersht, A. R. J. Mol. Biol. 1972, 64, 497.
77. (a) McDonald, I. K.; Thornton, J. M. J. Mol. Biol. 1994, 238, 777.
78. (b) Rashin, A. A.; Honig, B. J. Mol. Biol. 1984, 173, 515.
79. (a) Fersht, A. R.; Shi, J.-P.; Knill-Jones, J.; Lowe, D. M.; Wilkinson, A. J.; Blow, D. M.; Brick, P.; Carter, P.; Waye, M. M. Y.; Winter, G. Nature (London) 1985, 314, 235.
80. (b) Tissort, A. C.; Vuilleumier, S.; Fersht, A. R. Biochemistry 1996, 35, 6786.
81. (c) Serrano, L.; Horovitz, A.; Avron, B.; Bycroft, M.; Fersht, A. R. Biochemistry 1990, 29, 9343.
82. (d) Marquesee, S.; Baldwin, R. L. Proc. Natl. Acad. Sci. U.S.A. 1987, 84, 8898.
83. (e) Anderson, D. E.; Becktel, W. J.; Dahlquist, F. W. Biochemistry 1990, 29, 2403.
84. (a) Yip, K. S.; Stilman, T. J.; Britton, K. L.; Artymiuk, P. J.; Baker, P. J.; Sedelnikova, S. E.; Engel, P. C.; Pasquo, A.; Chiaraluc, R.; Consalvi, V. Structure 1995, 3, 1147.
85. (b) Hennig, M.; Darimont, B.; Sterner, R.; Kirschner, K.; Jansonius, J. N. Structure 1995, 3, 1295.
86. (c) Pappenberger, G.; Schurig, H.; Jaenicke, R. J. Mol. Biol. 1997, 274, 676.
87. (a) Dao-pin, S.; Sauer, U.; Nicholson, H.; Mattews, B. W. Biochemistry 1991, 30, 7142.
88. (b) Lumb, K. J.; Kim, P. S. Science (Washington, D. C.) 1995, 268, 436.
89. (a) Hendsch, Z. S.; Tidor, B. Protein Sci. 1994, 3, 211.
90. (b) Kumar, S.; Nussinov, R. Protein 2001, 43, 433.
91. (c) Takano, K.; Tsuchimori, K.; Yamagata, Y.; Yutani, K. Biochemistry 2000, 39, 12375.
92. (a) Musafia, B.; Buchner, V.; Arad, D. J. Mol. Biol. 1995, 254, 761.
93. (b) Xiao, L.; Honig, B. J. Mol. Biol. 1999, 289, 1435.