Assembly of Molecular Solids via Non-covalent Interactions

Making Crystals by Design: Methods, Techniques and Applications

Volumn , Issue , 2007, Pages 209-240

  Aakeröy, Christer B ^a   Schultheiss, Nate ^a  

^a KANSAS STATE UNIVERSITY   (United States)

Author keywords

Assembly of molecular solids via non covalent interactions; Binary hydrogen bonded Co crystals; Design and synthesis of co crystals; Directed assembly of homomeric molecular solids; Hydrogen bond interactions

Indexed keywords

EID: 84889627417     PISSN: None     EISSN: None     Source Type: Book    
DOI: 10.1002/9783527610112.ch8     Document Type: Chapter

References (210)

1. J.-M. Lehn, Angew. Chem. Int. Ed. Engl. 1990, 29,1304.
2. G. R. Desiraju, Crystal Engineering: The Design of Organic Solids, Elsevier, Amsterdam, 1989.
3. C. V. K. Sharma, J. Chem. Ed. 2001, 78, 617.
4. J. L. Atwood, J. E. D. Davies, D. D. MacNicol, F. Vçgtle, K. S. Suslick (Eds.), Comprehensive Supramolecular Chemistry, Elsevier, Oxford, 1996.
5. J. W. Steed, J. L. Atwood, Supramolecular Chemistry: An Introduction, J.Wiley & Sons, Chichester, 2000.
6. C. B. Aakerçy, Acta Crystallogr., Sect. B 1997, 53, 569.
7. G. R. Desiraju, Nature 2001, 412, 397.
8. E. Coronado, J. R Galan-Mascaros, C. J. Gomez-Garcia, V. Laukhin, Nature 2000, 408, 447.
9. M. Muthuraman, R. Masse, J.-F. Nicoud, G. R. Desiraju, Chem. Mater. 2001, 13, 1473.
10. O. Kçnig, H.-B. Burgi, T. Armbruster, J. Hulliger, T. Weber, J. Am. Chem. Soc. 1997, 119, 10632.
11. O. Kahn, Acc. Chem. Res. 2000, 33, 1
12. J. S. Miller, Inorg. Chem. 2000, 39, 4392.
13. Y. Aoyama, Top. Curr. Chem. 1998, 198, 131.
14. D. M. Bassani, V. Darcos, S. Mahony, J.-P. Desvergne, J. Am.Chem. Soc. 2000, 122, 8795.
15. J.-M. Lehn, Supramolecular Chemistry, VCH, Weinheim, 1995.
16. E. J. Corey, Chem. Soc. Rev. 1988, 17, 111.
17. K. C. Nicolaou, E. J. Sorensen, Classics in Total Synthesis, Wiley-VCH, Weinheim, 1996.
18. B. Moulton, M. J. Zaworotko, Chem. Rev. 2001, 101, 1629.
19. G. R. Desiraju, Acc. Chem. Res. 2002, 35, 565.
20. K. T. Holman, A. M. Pivovar, J. A. Swift, M. D. Ward, Acc. Chem. Res. 2001, 34, 107.
21. Crystal engineering: From molecules and crystals to materials, A NATO Advanced Study Institute and a Euroconference, D. Braga, F. Grepioni, A.G. Orpen (Eds.) Erice, Italy, 1999, 58.
22. C. B. Aakerçy, A. M. Beatty, Aus. J. Chem. 2001, 54, 409.
23. M. W. Hosseini, CrystEngComm. 2004, 6, 318.
24. L. MacGillivray, CrystEngComm. 2004, 6, 77.
25. L. Brammer, Chem. Soc. Rev. 2004, 33, 476.
26. L. J. Prins, D. N. Reinhoudt, P. Timmerman, Angew. Chem. Int. Ed. 2001, 40, 2382.
27. D. C. Sherrington, K. A. Taskinen, Chem. Soc. Rev. 2001, 30, 83.
28. G. M. Whitesides, E. E. Simanek, J. P. Mathias, C. T. Seto, D. N. Chin, M. Mammen, D. M. Gordon, Acc. Chem. Res. 1995, 28, 37.
29. N. J. Turro, Chem. Commun. 2002, 2279.
30. G. R. Desiraju, Angew. Chem. Int. Ed. Engl. 1995, 34, 2311.
31. A. Nangia, G. R. Desiraju, Acta Crystallogr., Sect. A 1998, 54, 934.
32. An extensive discussion on 'weaker' or unconventional hydrogen bonds is provided by T. Steiner, G. R. Desiraju, in The Weak Hydrogen Bond in Structural Chemistry and Biology, Oxford University Press, New York, 1999.
33. M. M. Conn, J. Rebek, Jr. Chem. Rev. 1997, 97, 1647.
34. D. S. Lawrence, T. Jiang, M. Levett, Chem. Rev. 1995, 95, 2229.
35. P. Stang, B. Olenyuk, Acc. Chem. Res. 1997, 30, 502.
36. M. Fujita, Chem. Soc. Rev. 1998, 27, 417.
37. B. Linton, A. D. Hamilton, Chem. Rev. 1997, 97, 1669.
38. C. T. Seto, G. M. Whitesides, J. Am. Chem. Soc. 1991, 113, 712.
39. C. B. Aakerçy, K. R. Seddon, Chem. Soc. Rev. 1993, 22, 397.
40. S. Subramanian, M. J. Zaworotko, Coord. Chem. Rev. 1994, 137, 357.
41. J.-M. Lehn, M. Mascal, A. DeCian, J. Fischer, J. Chem. Soc., Perkin Trans. 2, 1992, 461.
42. X. Zhao, Y.-L. Chang, F. W. Fowler, J. W. Lauher, J. Am. Chem. Soc. 1990, 112, 6627.
43. M.W. Hosseini, CrystEngComm. 2004, 6, 318.
44. L. R. MacGillivray, CrystEngComm. 2004, 6, 77.
45. L. Brammer, Chem. Soc. Rev. 2004, 33, 476.
46. D. L. Caulder, K. N. Raymond, Acc. Chem. Res. 1999, 32, 975.
47. D. N. Reinhoudt, M. Crego-Calama, Science 2002, 295, 2403.
48. J.-M. Lehn, Science 2002, 295, 2400.
49. A. Marsh, M. Silvestri, J.-M. Lehn, Chem. Commun. 1996, 1527.
50. F. H. Beijer, H. Kooijman, A. L. Spek, R. P. Sijbesma, E. W. Mejer, Angew. Chem. Int. Ed. Engl. 1998, 37, 75.
51. W. Jaunky, M. W. Hosseini, J. M. Planeix, A. De Cian, N. Kyritsakas, J. Fischer, Chem. Commun. 1999, 2313.
52. J. Toussaint, Acta Crystallogr. 1951, 4, 71.
53. R. S. Miller, I. C. Paul, D. Y. Curtin, J. Am. Chem. Soc. 1974, 96, 6334.
54. M. Colapietro, A. Domenicano, Acta Crystallogr., Sect. B. 1982, 38, 1953.
55. H. Takazawa, S. Ohba, Y. Saito, Acta Crystallogr., Sect. B. 1989, 45, 432.
56. K. Folting, W. M. Lipscomb, B. Jerslev, Acta Crystallogr. 1964, 17, 1263.
57. E. Arte, J. P. Declercq, G. German, M. van Meerssche, Bull. Soc. Chim. Belg. 1980, 89, 155.
58. Å. Kvick, S. S. Booles, Acta Crystallogr., Sect. B. 1972, 28, 3405.
59. Å. Kvick, M. Backeus, Acta Crystallogr., Sect. B. 1974, 30, 474.
60. A. Kvick, R. Thomas, T. F. Koetzle, Acta Crystallogr., Sect. B. 1976, 32, 224.
61. B. R. Penfold, J. C. B White, Acta. Crystallogr. 1959, 12, 130.
62. C. B. Aakerçy, J. Desper, E. Elisabeth, B. A. Helfrich, B. Levin, J. F. Urbina, Z. Kristallogr. 2005, 220, 325.
63. M. Bailey, C. J Brown, Acta. Crystallogr. 1967, 22, 387.
64. E. A. Burton, L. Brammer, F. C. Pigge, C. Aakerçy, D. Leinen, New. J. Chem. 2003, 27, 1084-1094.
65. K. G. Jensen, Acta. Chem. Scand. 1970, 24, 3293.
66. Y. Ducharme, J. D. Wuest, J. Org. Chem. 1988, 53, 5787.
67. D. J. Duchamp, R. E. Marsh, Acta. Crystallogr., Sect. B. 1969, 25, 5.
68. Y-H. Chang, M-A. West, F. W. Fowler, J. W. Lauher, J. Am. Chem. Soc. 1993, 115, 5991
69. S. Coe, J. J. Kane, T. L Nguyen, L. M. Toledo, E. Wininger, F. W. Fowler, J. W. Lauher, J. Am. Chem. Soc. 1997, 119, 86.
70. T. L. Nguyen, A. Scott, B. Dinkelmeyer, F. W. Fowler, J. W. Lauher, New J. Chem. 1998, 2, 129.
71. L. Leiserowitz, Acta Crystallogr., Sect. B 1976, 32, 775.
72. O. Ermer, J. Am. Chem. Soc. 1998, 110, 3747.
73. O. Saied, T. Maris, J. D. Wuest, J. Am. Chem. Soc. 2003, 125, 14956.
74. X. Wang, M. Simard, J. D. Wuest, J. Am. Chem. Soc. 1994, 116, 12119
75. M. Simard, D. Su, J. D. Wuest, J. Am. Chem. Soc. 1991, 113, 4696.
76. P. Metrangolo, H. Neukirch, T. Pilati, G. Resnati, Acc. Chem. Res. 2005, 38, 386
77. P. Metrangolo, G. Resnati, Chem.-Eur. J. 2001, 12, 2511.
78. G. R. Desiraju, R. L. Harlow, J. Am. Chem. Soc. 1989, 111, 6757.
79. A. D. Bond, J. Griffiths, J. M. Rawson, J. Hulliger, Chem Commun. 2001, 2488.
80. B. Ahrens, P. G. Jones, Acta Crystallogr., Sect. C. Cryst. Struct. Commun. 1999, 55, 1308.
81. A. C. B Lucassen, M. Vartanian, G. Leitus, M. van der Boom, Cryst. Growth Des. 2005, 5, 1671.
82. R. B. Walsh, C. W. Padgett, P. Metrangolo, G. Resnati, T. W. Hanks, W. T. Pennington, Cryst. Growth Des. 2001, 1, 165.
83. A. Hinchliffe, R.W. Munn, R. G. Pritchard, C. J. Spicer, J. Mol. Struct. 1985, 130, 93.
84. A. Maiga, Y. Haget, M. A. Cuevas-Diarte, J. Appl. Crystallogr. 1984, 17, 210.
85. E. Estop, A. Alvarez-larena, A. Belaaraj, X. Solans, M. Labrador, Acta Crystallogr., Sect. C, 1997, 53, 1932.
86. V. R. Thalladi, H-C. Weiss, D. Blaser, R. Boese, A. Nangia, G. R. Desiraju, J. Am. Chem. Soc. 1998, 120, 8702.
87. J. D. Dunitz, ChemBioChem. 2004, 5, 614.
88. M. Bremer, P. S. Gregory, P. V. R. Schleyer, J. Org. Chem. 1989, 54, 3796.
89. V. R. Pedireddi, D. S. Reddy, B. S. Goud, D. C. Craig, A. D. Rae, G. R. Desiraju, J. Chem. Soc. Perkin Trans. 2 1994, 2353.
90. G. R. Desiraju, Angew. Chem. Int. Ed. Engl. 1995, 34, 2311.
91. J. D. Dunitz, in Perspectives in Supramolecular Chemistry: The Crystal as a Supramolecular Entity, G. R. Desiraju (Ed.), Wiley, Amsterdam, 1995.
92. M. C. Etter, D. A. Adsmond, J. Chem. Soc., Chem. Commun. 1990, 589.
93. M. C. Etter, P. W. Baures, J. Am. Chem. Soc.1988, 110, 639.
94. M. C. Etter, Acc. Chem. Res. 1990, 23, 120.
95. M. C. Etter, J. Phys. Chem. 1991, 95, 4601.
96. G. R. Desiraju, CrystEngComm, 2003, 5, 466.
97. J. D. Dunitz, CrystEngComm, 2003, 5, 506.
98. This requirement may be deemed overly restrictive but it does offer an important distinction between solvates and cocrystals. However, in same cases, notably in the work by Boese and coworkers, it is clear that in their elegant work using low-temperature crystallizations they intentionally prepare co-crystals with a very clear and deliberate strategy (see e.g. M. T. Kirchner, R. Boese, A. Gehrke, D. Blaeser, CrystEngComm. 2004, 6, 360.)
99. For information about classic chargetransfer compounds, see J. Rose, Molecular Complexes, Pergamon Press, Oxford, 1967.
100. S. Shan, E. Batchelor, W. Jones, Tetrahedron Lett. 2002, 43, 8721
101. P. Vishweshwar, R. Thaimattam, M. Jaskolski, G. R. Desiraju, Chem. Commun. 2002, 1830.
102. P. Vishweshwar, A. Nangia, V. M. Lynch, CrystEngComm. 2003, 5.
103. Ö. Almarsson, M. J. Zaworotko, Chem. Commun. 2004, 1889.
104. G. R. Desiraju, J. A. R. P. Sarma, J. Chem. Soc., Chem. Commun. 1983, 45
105. F. Pan, W. S. Wong, V. Gramlich, C. Bosshard, P. Gunter, J. Chem. Soc.,Chem. Commun. 1996, 2
106. V. R. Pedireddi, W. Jones, A. P. Chorlton, R. Docherty, J. Chem. Soc., Chem. Commun. 1996, 997
107. S. H. Dale, M. R. J. Elsegood, M. Hemmings, A. L. Wilkinson, CrystEngComm, 2004, 6, 207
108. V. R. Pedireddi, J. PrakashaReddy, K. K. Arora, Tetrahedron Lett. 2003, 44, 4857.
109. C. B. Aakerçy, J. Desper, B. A. Helfrich, CrystEngComm 2004, 6, 19.
110. C. B. Aakerçy, A. M. Beatty, M. Nieuwenhuyzen, M. Zou, Tetrahedron 2000, 56, 6693.
111. J.-M. Lehn, M. Mascal, A. DeCian, J. Fischer, J. Chem. Soc., Chem. Commun. 1990, 479.
112. R. D. Bailey Walsh, M. W. Bradner, S. Fleischman, L. A. Morales, B. Moulton, N. Rodriguez-Hornedo, M. J. Zaworotko, Chem. Commun. 2003, 186.
113. L. R. MacGillivray, J. L. Reid, J. A. Ripmeester, J. Am. Chem. Soc., 2000, 122, 7817.
114. J. A. Zerkowski, J. C. MacDonald, G. M. Whitesides, Chem. Mater. 1997, 9, 1933.
115. J. J. Kane, R.-F. Liao, J. W. Lauher, F. W. Fowler, J. Am. Chem. Soc. 1995, 117, 12003.
116. P. Vishweshwar, A. Nangia, V. M. Lynch, J. Org. Chem. 2002, 67, 556.
117. C. Huang, L. Leiserowitz, G. M. Schmidt, J. Chem. Soc., Perkin Trans. 2 1973, 503.
118. F. A. Allen, P. R. Raithby, G. P. Shields, R. Taylor, J. Chem. Soc., Chem. Commun. 1998, 1043.
119. O. Ermer, J. Neudçrfl, Helv. Chim. Acta. 2001, 84, 1268
120. L. Leiserowitz, M. Tuval, Acta Crystallogr., Sect. B 1978, 34, 1230.
121. M. C. Etter, G. M. Frankenbach, Chem. Mater. 1989, 1, 10.
122. This observation was first made by J. Donohue J. Phys. Chem. 1952, 56, 502.
123. P. Metrangolo, T. Pilati, G. Resnati, A. Stevenazzi, Chem. Commun. 2004, 1492.
124. A. De Santis, A. Forni, R. Liantonio, P. Metrangolo, T. Pilati, G. Resnati, Chem. Eur. J. 2003, 9, 3974.
125. D. S. Reddy, D. C. Craig, G. R. Desiraju, Chem. Commun. 1994, 1457.
126. T. Dahl, O. Hassel, Acta Chem. Scand. 1970, 24, 377.
127. J. A. R. P. Sarma, G. R. Desiraju, J. Chem. Soc., Perkin Trans. 2 1985, 1905.
128. T. Sugiyama, J. Meng, T. Matsuura, J. Mol. Struct. 2002, 611, 53.
129. D. E. Lynch, G. Smith, D. Freney, K. A. Byriel, C. H. L. Kennard, Aust. J. Chem. 1994, 47, 1097.
130. L. R. Nassimbeni, H. Su, E. Weber, K. Skobridis, Cryst. Growth Des. 2004, 4, 85.
131. D. E. Lynch, T. Latif, G. Smith, K. A. Byriel, C. H. L. Kennard, S. Parsons, Aust. J. Chem. 1998, 51, 403.
132. J. Zhu, J.-M. Zheng, Chin. J. Struct. Chem. 2004, 23, 417.
133. C. B. Aakerçy, A. M. Beatty, B. A. Helfrich, J. Am. Chem. Soc. 2002, 124, 14425.
134. C. B. Aakerçy, A. M. Beatty, M. Zou, Cryst. Eng. 1998, 1, 225.
135. R. F. M. Lange, F. H. Beijer, R. P. Sijbesma, R. W.W. Hooft, H. Kooijman, A. L. Spek, J. Kroon, E. W. Meijer, Angew. Chem., Int. Ed, 1997, 36, 969.
136. J. A. Zerkowski, C. T. Seto, G.M. Whitesides, J. Am. Chem. Soc. 1992, 114, 5473.
137. M. Y. Antipin, A. I. Akhmedov, Y. T. Struchkov, E. I. Matrosov, M. I. Kabachnik, Zh. Strukt. Khim. 1983, 24, 86
138. D. E. Lynch, G. Smith, K. A. Byriel, C. H. L. Kennard, Acta Crystallogr., Sect. C: Cryst. Struct. Commun. 1993, 49, 718.
139. M. C. Etter, T. W. Panunto, J. Am. Chem. Soc. 1988, 110, 5896.
140. C. Glidewell, G. Ferguson, R. M. Gregson, A. J. Lough, Acta Crystallogr., Sect. C: Cryst. Struct. Commun. 1999, 55, 2133.
141. A. Ranganathan, V. R. Pedireddi, C. N. R. Rao, J. Am. Chem. Soc. 1999, 121, 1752.
142. A. De Santis, A. Forni, R. Liantonio, P. Metrangolo, T. Pilati, G. Resnati, Chem.-Eur. J. 2003, 9, 3974.
143. R. B.Walsh, C. W.Padgett, P.Metrangolo, G. Resnati, T.W. Hanks, W. T. Pennington, Cryst. Growth Des. 2001, 1, 165.
144. F. Garcia-Tellado, S. J. Geib, S. Goswami, A. D. Hamilton, J. Am. Chem. Soc., 1991, 113, 9265.
145. M. Tremayne, C. Glidewell, Chem. Commun. 2000, 2425.
146. O. Ermer, A. Eling, J. Chem. Soc., Perkin Trans. 2 1994, 925.
147. C. B. Aakerçy, J. Desper, B. Leonard, J. F. Urbina, Cryst. Growth Des. 2005, 3, 865.
148. C. B. Aakerçy, A. M. Beatty, B. A. Helfrich, M. Nieuwenhuyzen, Cryst. Growth Des. 2003, 3, 159.
149. T.-J. M. Luo, G. T. R Palmore, Cryst. Growth Des. 2002, 2, 337.
150. V. R. Pedireddi, S. Chatterjee, A. Ranganathan, C. N. R. Rao, J. Am. Chem. Soc. 1997, 119, 10867.
151. T. L. Nguyen, F. W. Fowler, J.W. Lauher, J. Am. Chem. Soc. 2001, 123, 11057.
152. J. Xiao, M. Yang, J. W. Lauher, F.W. Fowler, Angew. Chem., Int. Ed. 2000, 39, 2132.
153. F. H. Beijer, R. P. Sijbesma, J. A. J. M. Vekemans, E. W. Meijer, H. Kooijman, A. L. Spek, J. Org. Chem. 1996, 61, 6371.
154. B.-Q. Ma, P. Coppens, Chem. Commun. 2003, 2290.
155. P. Vishweshwar, A. Nangia, V. M. Lynch, Cryst. Growth Des. 2003, 3, 783.
156. S. G. Fleischman, S. S. Kuduva, J. A. McMahon, B. Moulton, R. D. B. Walsh, N. Rodriguez-Hornedo, M. J. Zaworotko, Cryst. Growth Des. 2003, 3, 909.
157. M. C. Etter, J. C. MacDonald, J. Bernstein, Acta Crystallogr., Sect. B. 1990, 46, 256.
158. J. Bernstein, R. E. Davis, L. Shimoni, N.-L.Chang, Angew. Chem., Int. Ed., Engl., 1995, 34, 1555.
159. C. P Brock, J. D. Dunitz, Acta Crystallogr., Sect. A 1991, 47, 854.
160. P. Kronenbusch, W. B. Gleson, D. Britton, Cryst. Struct. Commun. 1976, 5, 17.
161. D. Britton, J. Konnert, S. Lam, Cryst. Struct. Commun. 1977, 6, 45.
162. H. Quast, Y. Gorlach, E.-M. Peters, K. Peters, H. G. von Schnering, L. M. Jackman, G. Ibar, A. J. Freyer, Chem. Ber. 1986, 119, 1801.
163. Charge-transfer complexes are not included in this discussion
164. Several co-crystals have been constructed from heterocycles like bipyridin or pyrazine and activated iodo-containing compounds; see refs. [51] and [102].
165. F.A. Allen, Acta Crystallogr., Sect. B 2002, 58, 380.
166. F. Pan, W. S. Wong, V. Gramlich, C. Bosshard, P. Gunter, Chem. Commun. 1996, 2
167. J. A. Zerkowski, J. C. MacDonald, G.M. Whitesides, Chem. Mater. 1997, 9, 9.
168. R.-F. Liao, J. W. Lauher, F. W. Fowler, Tetrahedron, 1996, 52, 3153.
169. N. Shan, A. D. Bond, W. Jones, Cryst. Eng. 2002, 5, 9.
170. V. R. Pedireddi,W. Jones, A. P. Chorlton, R. Docherty, Chem. Commun. 1996, 997.
171. P. Vishweshwar, A. Nangia, V. M. Lynch, J. Org. Chem. 2002, 67, 556.
172. CSD codes: OCAYUM, OCASAT, and POFPAB
173. CSD codes: GURVOE, GURVUK, LUDFUL, UNECAR, ZUPKUQ, and ZUPLAX
174. CSD codes: BEQWAV, FIHYEA, FIJCIK, FIJCUW, HUPPOX, MUFNIK, NOPXIZ, OJENIA, PULWUO, RAPHAR, SUXVOW, UDUZIC, UDOZOI, UHELUO, XUNGIW, and XUNGOC
175. CSD code: POFPEF
176. CSD codes: CUFSET, LUSWEB, PANYIM, PANZEJ, PAPDIT, PAPFOB, UNEBOE, WUKREZ, and WUKROJ
177. CSDcodes: AJAKEB, AJAKIF, ASAXOH, ASAXUN, BUDWEC, BUDZUV, BUFBIP, BUFQAU, LUNMEM, LUNMIC, LUNMOW, and VAKTOR
178. C. V. K. Sharma, K. Panneerselvam, T. Pilati, G. R. Desiraju, J. Chem. Soc., Perkin Trans. 2 1993, 2209.
179. V. R. Pedireddi, J. PrakashReddy, Tetrahedron Lett. 2002, 43, 4927.
180. J. Bernstein, Polymorphism in Molecular Crystals, Oxford University Press, New York, 2002.
181. C. B. Aakerçy, M. Nieuwenhuyzen, S. L. Price, J. Am. Chem. Soc. 1998, 120, 8986.
182. Forms I and III of 4-chlorobenzamide: T. Taniguch, K. Nakata, Y. Takaki, K. Sakurai, Acta Crystallogr. Sect. B 1978, 34, 2574.
183. Form II: T. Hayashi, K. Nakata, Y. Takaki, K. Sakurai, Bull. Chem. Soc. Jpn. 1980, 53, 801.
184. P. D. Cradwick, Nature, 1975, 258, 774.
185. A. Katrusiak, Acta Crystallogr., Sect. C: Cryst. Struct. Commun. 1993, 49, 36.
186. A. Katrusiak, Acta Crystallogr., Sect. B: Struct. Sci. 2001, 57, 697.
187. C. B. Aakerçy, A. M. Beatty, D. S. Leinen, CrystEngComm. 2002, 4, 310.
188. J. Valdés-Martínez, M. Del Rio-Ramirez, S. Hern ndez-Ortega, C. B. Aakerçy, B. A. Helfrich, Cryst. Growth Des. 2001, 2, 485
189. C. B. Aakerçy, A. M. Beatty, M. Tremayne, D. M. Rowe, C. C. Seaton, Cryst. Growth Des. 2001, 2, 377.
190. C. B. Aakerçy, A. M. Beatty, D. S. Leinen, Cryst. Growth Des. 2000, 1, 47.
191. C. B. Aakerçy, A. M. Beatty , M. Nieuwenhuyzen, M. Zou, J. Mater. Chem. 1998, 8, 1385.
192. A. D. Burrows, Struct. Bond., 2004, 111, 55.
193. C. B.Aakerçy,A.M.Beatty, B.A.Helfrich, Angew. Chem., Int. Ed. 2001, 40, 3240.
194. If the acid is too strong, the proton will be transferred to the nitrogen atom resulting in an ionic compound and not a co-crystal. Some examples of crystal engineering of ionic systems include e.g., J. A. Swift, A. M. Pivovar, A. M. Reynolds, M. D. Ward, J. Am. Chem. Soc., 1998, 120, 5887.
195. F. Xue, T. C. W. Mak, J. Phys. Org. Chem. 2000, 13, 405.
196. P. Cudic, J.-P. Vigneron, J.-M. Lehn, M. Cesario, T. Prangé, Eur. J. Org. Chem. 1999, 2479
197. C. V. K. Sharma, A. Clearfield, J. Am. Chem. Soc. 2000, 122, 4394.
198. S. Ferlay, R. Holakovsky, M. W. Hosseini, J.-M. Planeix, N. Kyritsakas, Chem. Commun.2003, 1224.
199. C. B. Aakerçy, P. B. Hitchcock, K. R. Seddon, J. Chem. Soc., Chem. Commun. 1992, 553.
200. C. B. Aakerçy, D. P. Hughes M. Nieuwenhuyzen, J. Am. Chem. Soc. 1996, 118, 10134.
201. A. M. Beatty, K. E. Granger, A. E. Simpson, Chem.-Eur. J. 2002, 8, 3254.
202. A. M. Beatty, C. L. Schneider, A. E. Simpson, J. L. Zaher, CrystEngComm. 2002, 4, 282.
203. D. Braga, L. Maini, M. Polito, F. Grepioni, Struct. Bond. 2004, 111, 1.
204. L. Leiserowitz, F. Nader, Acta Crystallogr., Sect. B: Struct. Sci. 1977, 33, 2719.
205. All pKa/pKb values from G. Kartum, W. Vogel, K. Andrussov, Dissociation Constants of Organic Acids in Aqueous Solution, Butterworth & Co., London, 1961.
206. C. B. Aakerçy, J. Desper, J. F. Urbina, Chem. Commun. 2005, 2820.
207. An estimate for the differences in basicity between the pyridyl and the benzimidazol-1-yl moieties were obtained by calculating pKa values for the conjugated acids of the two hydrogenbond acceptors in each SR. 3-(benzimidazol-1-yl)methylpyridine: pKa = 4.71 ± 0.10 and 5.72 ±0.30 for pyridyl and benzimidazol-1-yl moieties, respectively. 3-(2-methylbenzimidazol-1-yl)methylpyridine: pKa = 4.72 ±0.10 and 5.85 ± 0.18 for pyridyl and benzimidazol-1-yl moieties, respectively. Calculations were performed using Advanced Chemistry Development (ACD/Labs) Software Solaris V4.76 (© 1994-2005 ACD/Labs).
208. M. H. Abraham, Chem. Soc. Rev. 1993, 22, 73.
209. S. Shan, S. Loh, D. Herschlag, Science, 1996, 272, 97.
210. 3,5-dinitrobenzoic acid (pKa=2.8); 4-nitrobenzoic acid (pKa= 3.44); 3-N,N-(dimethylamino) benzoic acid (pKa= 4.30).