Reactions between or within molecular crystals

Angewandte Chemie - International Edition

Volumn 43, Issue 31, 2004, Pages 4002-4011

  Braga, Dario ^a   Grepioni, Fabrizia ^b  

^a UNIVERSITY OF BOLOGNA   (Italy)

^b UNIVERSITY OF SASSARI   (Italy)

Author keywords

Crystal engineering; Mechanochemistry; Solid state reactivity; Solventless reactions; Supramolecular chemistry

Indexed keywords

CHEMICAL BONDS; COMPLEXATION; GRINDING (MACHINING); MILLING (MACHINING); REACTION KINETICS; SUPRAMOLECULAR CHEMISTRY;

CYCLOADDITIONS; SUPRAMOLECULAR BONDING;

MOLECULAR CRYSTALS;

CYCLODEXTRIN;

BINDING AFFINITY; COVALENT BOND; CRYSTAL STRUCTURE; CYCLOADDITION; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; REACTION ANALYSIS; SHORT SURVEY; SOLID; SUPRAMOLECULAR CHEMISTRY; THERMOGRAVIMETRY; X RAY POWDER DIFFRACTION;

EID: 4544270702     PISSN: 14337851     EISSN: None     Source Type: Journal    
DOI: 10.1002/anie.200301721     Document Type: Short Survey

References (158)

1. a) D. Bradley, Chem. Br. 2002, 12, September, 42;
2. b) K. Tanaka, E Toda, Chem. Rev. 2000, 100, 1025;
3. c) K. Tanaka, Solvent-free Organic Synthesis, Wiley-VCH, Weinheim, 2003.
4. a) G. W. V. Cave, C. L. Raston, J. L. Scott, Chem. Commun. 2001, 2159;
5. b) G. Rothenberg, A. P. Downie, C. L. Raston, J. L. Scott, J. Am. Chem. Soc. 2001, 123, 8701.
6. P. T. Anastas, J. C. Warner, Green Chemistry: Theory and Practice, Oxford University Press, New York, 1998.
7. G. Kaupp, CrystEngComm 2003, 5, 117.
8. a) V. V. Boldyrev, K. Tkacova, J. Mater. Synth. Process. 2000, 8, 121;
9. b) J. F. Fernandez-Bertran, Pure Appl. Chem. 1999, 71, 581.
10. a) T. Luty, C. J. Eckhardt, J. Am. Chem. Soc. 1995, 117, 2441;
11. b) Y. Ohashi, Acc. Chem. Res. 1988, 21, 268;
12. c) N. J. Coville, D. C. Levendis, Eur. J. Inorg. Chem. 2002, 3067.
13. See for example: a) S. Ariel, S. Askari, J. R. Scheffer, J. Trotter, J. Org. Chem. 1989, 54, 4324;
14. b) P. R. Pokkuluri, J. R. Scheffer, J. Trotter, M. Yap, J. Org. Chem. 1992, 57, 1486;
15. E. Cheung, T. Kanf, J. R. Scheffer, J. Trotter, Chem. Commun. 2000, 2309.
16. a) G. Pellizzari, Gazz. Chim. Ital. 1884, 14, 362;
17. b) I. C. Paul, D. Y. Curtin, Science 1975, 187, 19.
18. A. K. Cheetham, P. Day, Solid State Chemistry Techniques, Clarendon, Oxford, 1987.
19. a) K. D. M. Harris, M. Tremayne, Chem. Mater. 1996, 8, 2554;
20. b) K. D. M. Harris, M. Tremayne, B. M. Kariuki, Angew. Chem. 2001, 113, 1674; Angew. Chem. Int. Ed. 2001, 40, 1626.
21. b) K. D. M. Harris, M. Tremayne, B. M. Kariuki, Angew. Chem. 2001, 113, 1674; Angew. Chem. Int. Ed. 2001, 40, 1626.
22. a) D. Braga, F. Grepioni, Chem. Soc. Rev. 2000, 29, 229;
23. b) D. Braga, F. Grepioni in Crystal Design, Structure and Function. Perspectives in Supramolecular Chemistry, Vol. 7 (Ed. G. R. Desiraju), Whiley, Chichester, UK, 2003.
24. a) G. Kaupp, J. Schmeyers, Chem. Eng. Sci. 2002, 57, 763;
25. b) G. Kaupp, M. R. Naimi-Jamal, H. Ren, H. Zoz, Chem. Tech. 2002, 31, 206.
26. V. Kohlschütter, Z. Anorg. Allg. Chem. 1918, 105, 121.
27. a) G. M. J. Schmidt, Pure Appl. Chem. 1971, 43, 647;
28. b) M. D. Cohen, Angew. Chem. 1975, 87, 439; Angew. Chem. Int. Ed. Engl. 1975, 14, 386;
29. b) M. D. Cohen, Angew. Chem. 1975, 87, 439; Angew. Chem. Int. Ed. Engl. 1975, 14, 386;
30. c) M. D. Cohen, G. M. J. Schmidt, J. Chem. Soc. 1964, 1996;
31. d) G. A. Elgavi, B. S. Green, G. M. J. Schmidt, J. Am. Chem. Soc. 1973, 95, 2058.
32. M. A. Garcia-Garibay, Acc. Chem. Res. 2003, 36, 491.
33. F. Toda, Top. Curr. Chem. 1987, 140, 43.
34. a) G. Kaupp, D. Matthies, Chem. Ber. 1986, 119, 2387;
35. b) G. Kaupp, J. Schmeyers, J. Boy, Chemosphere 2001, 43, 55;
36. c) G. Kaupp, J. Schmeyers, J. Boy, Tetrahedron 2000, 56, 6899;
37. d) G. Kaupp in Comprehensive Supramolecular Chemistry, Vol. 8 (Ed. J. E. D. Davies), Elsevier, Oxford, 1996, pp. 381-423.
38. L. R. MacGillivray, CrystEngComm 2002, 4, 37.
39. G. W. Coates, A. R. Dunn, L. M. Henling, J. W. Ziller, E. B. Lobkovsky, R. H. Grubbs, J. Am. Chem. Soc. 1998, 120, 3641.
40. a) T. Odani, A. Matsumoto, CrystEngComm 2002, 4, 467;
41. b) A. Matsumoto, K. Sada, K. Tashiro, M. Miyata, T. Tsubouchi, T. Tanaka, T. Odani, S. Nagahama, T. Tanaka, K. Inoue, S. Saraghi, S. Nakamoto, Angew. Chem. 2002, 114, 2612; Angew. Chem. Int. Ed. 2002, 41, 2502.
42. b) A. Matsumoto, K. Sada, K. Tashiro, M. Miyata, T. Tsubouchi, T. Tanaka, T. Odani, S. Nagahama, T. Tanaka, K. Inoue, S. Saraghi, S. Nakamoto, Angew. Chem. 2002, 114, 2612; Angew. Chem. Int. Ed. 2002, 41, 2502.
43. K. S. Feldman, R. F. Campbell, J. Org. Chem. 1995, 60, 1924.
44. a) Y. Ito, B. Borecka, J. Trotter, J. R. Scheffer, Tetrahedron Lett. 1995, 36, 6083;
45. b) Y. Ito, B. Borecka, G. Olovsson, J. Trotter, J. R. Scheffer, Tetrahedron Lett. 1995, 36, 6087.
46. a) L. R. MacGillivray, J. L. Reid, J. A. Ripmeester, J. Am. Chem. Soc. 2000, 122, 7817;
47. b) G. S. Papaefstathiou, A. J. Kipp, L. R. MacGillivray, Chem. Commun. 2001, 2462;
48. c) D. B. Varshney, G. S. Papaefstathiou, L. R. MacGillivray, Chem. Commun. 2002, 1964;
49. d) T. Friščić, L. R. MacGillivray, Chem. Commun. 2003, 1306;
50. e) X. Gao, T. Friščić, L. MacGillivray, Angew. Chem. 2004, 116, 234; Angew. Chem. Int. Ed. 2004, 43, 232.
51. e) X. Gao, T. Friščić, L. MacGillivray, Angew. Chem. 2004, 116, 234; Angew. Chem. Int. Ed. 2004, 43, 232.
52. a) K. Novak, V. Enkelmann, G. Wegner, K. B. Wagener, Angew. Chem. 1993, 105, 1678; Angew. Chem. Int. Ed. Engl. 1993, 32, 1614;
53. a) K. Novak, V. Enkelmann, G. Wegner, K. B. Wagener, Angew. Chem. 1993, 105, 1678; Angew. Chem. Int. Ed. Engl. 1993, 32, 1614;
54. b) V. Enkelmann, G. Wegner, K. Novak, K. B. Wagener, J. Am. Chem. Soc. 1993, 115, 10 390.
55. a) M. Irie, S. Kobatake, M. Horichi, Science 2001, 291, 1769;
56. b) M. Morimoto, S. Kobatake, M. Irie, Chem. Eur. J. 2003, 9, 621;
57. c) S. Yamamoto, K. Matsuda, M. Irie, Angew. Chem. 2003, 115, 1674; Angew. Chem. Int. Ed. 2003, 42, 1636.
58. c) S. Yamamoto, K. Matsuda, M. Irie, Angew. Chem. 2003, 115, 1674; Angew. Chem. Int. Ed. 2003, 42, 1636.
59. a) G. Kaupp, Angew. Chem. 1992, 104, 606; Angew. Chem. Int. Ed. Engl. 1992, 31, 592;
60. a) G. Kaupp, Angew. Chem. 1992, 104, 606; Angew. Chem. Int. Ed. Engl. 1992, 31, 592;
61. b) G. Kaupp, Angew. Chem. 1992, 104, 609; Angew. Chem. Int. Ed. Engl. 1992, 31, 595.
62. b) G. Kaupp, Angew. Chem. 1992, 104, 609; Angew. Chem. Int. Ed. Engl. 1992, 31, 595.
63. K. Tanaka, F. Toda, E. Mochizuki, N. Yasui, Y. Kai, I. Miyahara, K. Hirotsu, Angew. Chem. 1999, 111, 3733; Angew. Chem. Int. Ed. 1999, 38, 3523.
64. K. Tanaka, F. Toda, E. Mochizuki, N. Yasui, Y. Kai, I. Miyahara, K. Hirotsu, Angew. Chem. 1999, 111, 3733; Angew. Chem. Int. Ed. 1999, 38, 3523.
65. I. Turowska-Tyrk, Chem. Eur. J. 2001, 7, 3401.
66. L. M. Greig, B. M. Kariuki, S. Habershon, N. Spencer, R. L. Johnston, K. D. M. Harris, D. Philp, New J. Chem. 2002, 26, 701.
67. a) J. Xiao, M. Yang, J. W. Lauher, F. W. Fowler, Angew. Chem. 2000, 112, 2216; Angew. Chem. Int. Ed. 2000, 39, 2132;
68. a) J. Xiao, M. Yang, J. W. Lauher, F. W. Fowler, Angew. Chem. 2000, 112, 2216; Angew. Chem. Int. Ed. 2000, 39, 2132;
69. b) F. W. Fowler, J. W. Lauher, J. Phys. Org. Chem. 2000, 13, 850;
70. c) X. Ouyang, F. W. Fowler, J. W. Lauher, J. Am. Chem. Soc. 2003, 125, 12 400.
71. J. G. Nery, G. Bolbach, I. Weissbuch, M. Lahav, Angew. Chem. 2003, 115, 2207; Angew. Chem. Int. Ed. 2003, 42, 2157.
72. J. G. Nery, G. Bolbach, I. Weissbuch, M. Lahav, Angew. Chem. 2003, 115, 2207; Angew. Chem. Int. Ed. 2003, 42, 2157.
73. a) J. R. Scheffer, Can. J. Chem. 2001, 79, 349;
74. b) B. O. Patrick, J. R. Scheffer, C. Scott, Angew. Chem. 2003, 115, 3905; Angew. Chem. Int. Ed. 2003, 42, 3775.
75. b) B. O. Patrick, J. R. Scheffer, C. Scott, Angew. Chem. 2003, 115, 3905; Angew. Chem. Int. Ed. 2003, 42, 3775.
76. a) R. P. Rastogi, P. S. Bassi, S. L. Chadha, J. Phys. Chem. 1963, 67, 2569;
77. b) R. P. Rastogi, N. B. Singh, J. Phys. Chem. 1966, 70, 3315;
78. c) R. P. Rastogi, N. B. Singh, J. Phys. Chem. 1968, 72, 4446.
79. M. C. Etter, J. Phys Chem. 1991, 95, 4601.
80. M. C. Etter, S. M. Reutzel, C. G. Choo, J. Am. Chem. Soc. 1993, 115, 4411.
81. W. H. Ojala, M. C. Etter, J. Am. Chem. Soc. 1992, 114, 10 228.
82. J. Bernstein, Polymorphism in Molecular Crystals, Oxford University Press, Oxford, 2002; see also J. Bernstein, R. J. Davey, J.-O. Henck, Angew. Chem. 1999, 111, 3646; Angew. Chem. Int. Ed. 1999, 38, 3440.
83. J. Bernstein, Polymorphism in Molecular Crystals, Oxford University Press, Oxford, 2002; see also J. Bernstein, R. J. Davey, J.-O. Henck, Angew. Chem. 1999, 111, 3646; Angew. Chem. Int. Ed. 1999, 38, 3440.
84. J. Bernstein, Polymorphism in Molecular Crystals, Oxford University Press, Oxford, 2002; see also J. Bernstein, R. J. Davey, J.-O. Henck, Angew. Chem. 1999, 111, 3646; Angew. Chem. Int. Ed. 1999, 38, 3440.
85. a) D. Y. Curtin, I. C. Paul, Acc. Chem. Res. 1973, 7, 217;
86. b) C. C. Chiang, C. T. Lin, A. H. J. Wang, D. Y. Curtin, I. C. Paul, J. Am. Chem. Soc. 1977, 99, 6303;
87. c) A. O. Patil, D. Y. Curtin, I. C. Paul, J. Am. Chem. Soc. 1984, 106, 348.
88. G. Crini, M. Morcellet, N. Morin, Actual. Chim. 2001, 11, 18.
89. a) M. R. Caira, D. R. Dodds, L. R. Nassimbeni, J. Therm. Anal. Calorim. 2002, 68, 647;
90. b) L. R. Nassimbeni, Acc. Chem. Res. 2003, 36, 631;
91. c) S. Apel, M. Lennartz, L. R. Nassimbeni, E. Weber, Chem. Eur. J. 2002, 8, 67 849.
92. a) L. R. Nassimbeni, CrystEngComm 2002, 5, 200;
93. b) S. J. Cantrill, G. J. Youn, J. F. Stoddart, D. J. Williams, J. Org. Chem. 2001, 66, 6857.
94. a) K. Uekama, F. Hirayama, T. Irie, Chem. Rev. 1998, 98, 2045;
95. b) S. A. Nepogodiev, J. F. Stoddart, Chem. Rev. 1998, 98, 1959;
96. c) A. Harada, Acc. Chem. Res. 2001, 34, 456;
97. d) S. Polarz, M. Antonietti, Chem. Commun. 2002, 2593.
98. I. Tsukushi, O. Yamamuro, H. Suga, Thermochim. Acta 1992, 200, 71.
99. J. Shailaja, S. Karthikeyan, V. Ramamurthy, Tetrahedron Lett. 2002, 43, 9335.
100. T. J. Brett, J. M. Alexander, J. L. Clark, C. R. Ross II, G. S. Harbison, J. J. Stezowski, Chem. Commun. 1999, 1275.
101. S. Watano, T. Okamoto, M. Tsuhari, I. Koizumi, Y. Osako, Chem. Pharm. Bull. 2002, 50, 341.
102. S. Watano, J. Furukawa, K. Miyanami, Y. Osako, Adv. Powder Technol. 2001, 12, 427.
103. N. Morin, A. Chilouet, J. Millet, J. C. Rouland, J. Therm. Anal. Calorim. 2000, 62, 187.
104. G. Bruni, A. Marini, V. Berbenni, R. Riccardi, R. M. Villa, J. Inclusion Phenom. Macrocyclic Chem. 1999, 35, 517.
105. a) F. Taneri, T. Guneri, Z. Aigner, M. Kata, J. Inclusion Phenom. Macrocyclic Chem. 2002, 44, 257;
106. b) R. Saikosin, T. Limpaseni, P. Pongsawadsi, J. Inclusion Phenom. Macrocyclic Chem. 2002, 44, 191.
107. Organic Solid-State Reactions (Ed.: F. Toda), Kluwer, Amsterdam, 2002.
108. a) F. Toda, H. Miyamoto, Chem. Lett. 1995, 861;
109. b) A. J. Schultz, G. D. Stucky, R. H. Blessing, P. Coppens, J. Am. Chem. Soc. 1976, 98, 3194, this paper reports the last X-ray determination of the structure of the tetrathiafulvalene with tetracyanoquinodimethane.
110. M. Yagi, S. Hirano, S. Toyota, F. Toda, P. Giastas, I. M. Mavridis, Heterocycles 2003, 59, 735.
111. F. Toda, H. Takumi, Enantiomer 1996, 1, 29.
112. a) R. Kuroda, Y. Imai, N. Tajima, Chem. Commun. 2002, 2848;
113. b) R. Kuroda, Y. Imai, T. Sato, Chirality 2001, 13, 588;
114. c) Y. Imai, N. Tajima, T. Sato, R. Kuroda, Chirality 2002, 14, 604.
115. M. R. Caira, L. R. Nassimbeni, A. F. Wildervanck, J. Chem. Soc. Perkin Trans. 2 1995, 2213.
116. a) D. Braga, L. Maini, M. Polito, L. Mirolo, F. Grepioni, Chem. Commun. 2002, 24, 2960;
117. b) D. Braga, L. Maini, M. Polito, L. Mirolo, F. Grepioni, Chem. Eur. J. 2003, 9, 4362.
118. a) F. Takusagawa, T. F. Koetzle, Acta Crystallogr. Sect. B 1979, 35, 2888;
119. b) G. J. Palenik, Inorg. Chem. 1969, 8, 2744.
120. D. Braga, G. Cojazzi, L. Maini, M. Polito, F. Grepioni, Chem. Commun. 1999, 1949.
121. a) T. L. Threlfall, Analyst 1995, 120, 2435;
122. b) N. Kubota, N. Doki, M. Yokota, D. Jagadesh, J. Chem. Eng. Jpn. 2002, 35, 1063.
123. P. Seiler, J. D. Dunitz, Acta Crystallogr. Sect. B 1982, 38, 1741.
124. R. J. Davey, N. Blagden, G. D. Potts, R. Docherty, J. Am. Chem. Soc. 1997, 119, 1767.
125. D. Braga, G. Cojazzi, D. Paolucci, F. Grepioni, CrystEngComm 2001, 1.
126. H. Koshima, M. Miyauchi, Cryst. Growth Des. 2001, 1, 355.
127. J. Dunitz, J. Bernstein, Acc. Chem. Res. 1995, 28, 193.
128. D. Braga, L. Maini, G. de Sanctis, K. Rubini, F. Grepioni, M. R. Chierotti, R. Gobetto, Chem. Eur. J. 2003, 9, 5538.
129. V. P. Balema, J. W. Wiench, M. Pruski, V. K. Pecharsky, Chem. Commun. 2002, 1606.
130. V. P. Balema, J. W. Wiench, M. Pruski, V. K. Pecharsky, Chem. Commun. 2002, 724.
131. V. P. Balema, J. W. Wiench, M. Pruski, V. K. Pecharsky, J. Am. Chem. Soc. 2002, 124, 6244.
132. a) P. J. Nichols, C. L. Raston, J. W. Steed, Chem. Commun. 2001, 1062;
133. b) W. J. Belcher, C. A. Longstaff, M. R. Neckenig, J. W. Steed, Chem. Commun. 2002, 1602.
134. A. Orita, L. S. Jiang, T. Nakano, N. C. Ma, J. Otera, Chem. Commun. 2002, 1362.
135. D. Braga, L. Maini, M. Polito, F. Grepioni, Chem. Commun. 2002, 2302.
136. N. Shan, F. Toda, W. Jones, Chem. Commun. 2002, 2372.
137. a) H. Günzler, H.-U. Gremlich, IR Spectroscopy, Wiley-VCH, Weinheim, 2002, chap. 4;
138. b) M. Falk, Vib. Spectrosc. 1990, 1, 69.
139. a) J. Fernandez-Bertran, E. Reguera, Solid State Ionics 1997, 93, 139;
140. b) A. Valor, J. Fernandez-Bertran, J. Radilla, J. Fluorine Chem. 2001, 107, 137;
141. c) J. Fernandez-Bertran, E. Reguera, Solid State Ionics 1997, 93, 139;
142. d) J. Fernandez-Bertran, E. Reguera, A. Paneque, H. Yee-Madeira, A. Gordillo-Sol, J. Fluorine Chem. 2002, 113, 93;
143. e) J. Fernandez-Bertran, J. Blanco Pascual, M. Hernandez, R. Rodriguez, React. Solids 1988, 5, 95;
144. f) J. Fernandez-Bertran, Solid State Ionics 1998, 112, 351.
145. J. Schmeyers, F. Toda, J. Boy, G. Kaupp, J. Chem. Soc. Perkin Trans. 2 1998, 989.
146. a) G.-W. Wang, K. Komatsu, Y. Murata, M. Shiro, Nature 1997, 387, 583;
147. b) K. Komatsu, G.-W. Wang, Y. Murata, T. Tanaka, K. Fujiwara, K. Yamamoto, M. Saunders, J. Org. Chem. 1998, 63, 9358.
148. a) Y. Murata, N. Kato, K. Fujiwara, K. Komatsu, J. Org. Chem. 1999, 64, 3483;
149. b) Y. Murata, N. Kato, K. Komatsu, J. Org. Chem. 2001, 66, 7235.
150. a) K. Komatsu, K. Fujiwara, Y. Murata, T. Braun, J. Chem. Soc. Perkin Trans. 1 1999, 2963;
151. b) K. Komatsu, K. Fujiwara, T. Tanaka, Y. Murata, Carbon 2000, 38, 1529;
152. c) K. Komatsu, K. Fujiwara, Y. Murata, Chem. Commun. 2000, 1583.
153. a) K. Komatsu, K. Fujiwara, Y. Murata, Chem. Lett. 2000, 1016;
154. b) Y. Murata, M. Suzuki, K. Komatsu, Chem. Commun. 2001, 2338
155. c) M. Kunitake, S. Uemura, O. Ito, K. Fujiwara, Y. Murata, K. Komatsu, Angew. Chem. 2002, 41, 1011; Angew. Chem. Int. Ed. 2002, 41, 969;
156. c) M. Kunitake, S. Uemura, O. Ito, K. Fujiwara, Y. Murata, K. Komatsu, Angew. Chem. 2002, 41, 1011; Angew. Chem. Int. Ed. 2002, 41, 969;
157. d) K. Fujiwara, K. Komatsu, Org. Lett. 2002, 4, 1039.
158. see for example D. Braga, G. R. Desiraju, J. Miller, A. G. Orpen, S. Price, CrystEngComm 2002, 4, 500.