198 Topics in Current Chemistry Editorial Board: A. de Meijere KN ...

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Functional Organic Zeolite Analogues 161 50. Kobayashi K, Endo K, Aoyama Y, Masuda H (1993) Tetrahedron Lett 34:7929 51. Aoyama Y, Endo K, Kobayashi K, Masuda H (1995) Supramol Chem 4:229 52. Endo K, Sawaki T, Koyanagi M, Kobayashi K, Masuda H, Aoyama Y (1995) J Am Chem Soc 117:8341 53. Endo K, Ezuhara T, Koyanagi M, Masuda H, Aoyama Y (1997) J Am Chem Soc 119:499 54. Brunet PB, Simard M, Wuest JD (1997) J Am Chem Soc 119:2723 55. Kobayashi K, Koyanagi M, Endo K, Masuda H, Aoyama Y (1998) Chem Eur J 4:417 56. Bhyrappa P, Wilson SR, Suslick KS (1997) J Am Chem Soc 119:8492 57. Hartgerink JD, Granja JR, Milligan RA, Ghadiri MR (1996) J Am Chem Soc 118:43 58. Yaghi OM, Davis CE, Li G, Li H (1997) J Am Chem Soc 119:2861 59. Wu LP, Yamamoto M, Kuroda-Sowa T, Maekawa M, Fukui J, Munakata M (1995) Inorg Chim Acta 239:165 60. Munakata M, Wu LP, Yamamoto M, Kuroda-Sowa T, Maekawa M (1996) J Am Chem Soc 118:3117 61. Ung AT, Gizachew D, Bishop R, Scudder ML, Dance IG, Craig DC (1995) J Am Chem Soc 117:8745 62. Russel VA, Etter MC, Ward MD (1994) J Am Chem Soc 116:1941 63. Davis ME, Robo RF (1992) Chem Mater 4:756 64. Yaghi OM, Li H, Groy TL (1996) J Am Chem Soc 118:9096 65. Endo K, Koike T, Sawaki T, Hayashida O, Masuda H, Aoyama Y (1997) J Am Chem Soc 119:4117 66. Aoyama Y, Endo K, Anzai T, Yamaguchi Y, Sawaki T, Kobayashi K, Kanehisa N, Hashimoto H, Kai Y, Masuda H (1996) J Am Chem Soc 118:5562 67. Toda F, Tanaka K, Miyahara I, Atsutsu S, Hirotsu K (1994) J Chem Soc Chem Commun 1994:1795 68. Korkas PP, Weber E, Czugler M, Náray-Szabó G (1995) J Chem Soc Chem Commun 1995:2229 69. Marjo CE, Bishop R, Craig DC, O’Brien A, Scudder ML (1994) J Chem Soc Chem Commun 1994:2513 70. Toda F, Tanaka K, Mak TCW (1985) Bull Chem Soc Jp, 58:2221 71. Gardner GB, Kiang Y-H, Lee S, Asgaonkar A, Venkataraman D (1996) J Am Chem Soc 118:6946 72. Kondo M, Yoshitomi T, Seki K, Matsuzaka H, Kitagawa S (1977) Angew Chem Int Ed Engl 36:1725 73. Yaghi OM, Li H (1996) J Am Chem Soc 118:295 74. Yaghi OM, Li H (1995) J Am Chem Soc 117:10,401 75. Dewa T, Aoyama Y (unpublished results) 76. Scott JL (1995) J Chem Soc Perkin Trans 2 495 77. Hawkins SC, Bishop R, Dance IG, Lipari T, Craig DC, Scudder ML (1993) J Chem Soc Perkin Trans 2 1729 78. Aoyama Y, Imai Y, Endo K, Kobayashi K (1995) Tetrahedron 51:343 79. Sawaki T, Endo K, Kobayashi K, Hayashida O,Aoyama Y (1998) Bull Chem Soc Jpn 70:3075 80. Sawaki T, Dewa T, Aoyama Y (submitted for publication)
Crystalline Polymorphism of Organic Compounds Mino R. Caira Department of Chemistry, University of Cape Town, Rondebosch 7700, South Africa. E-mail: xraymino@psipsy.uct.ac.za Crystal polymorphism is encountered in all areas of research involving solid substances. Its occurrence introduces complications during manufacturing processes and adds another dimension to the complexity of designing materials with specific properties. Research on polymorphism is fraught with unique difficulties due to the subtlety of polymorphic transformations and the inadvertent formation of pseudopolymorphs. In this report, a summary of thermodynamic, kinetic and structural considerations of polymorphism is presented. A wide variety of techniques appropriate to the study of organic crystalline polymorphism and pseudopolymorphism is then surveyed, ranging from simple crystal density measurement to observation of polymorphic transformations using variable-temperature synchrotron X-ray diffraction methods. Application of newer methodology described in this report is yielding fresh insights into the nature of the crystallization process, holding promise for a deeper understanding of the phenomenon of polymorphism and its practical control. Keywords: Crystal polymorphism, Pseudopolymorphism, Crystallization. 1 Introduction . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 164 2 Crystal Polymorphism – Theoretical Principles and Practical Implications . . . . . . . . . . . . . . . . . . . . . . . . 165 2.1 Background – The Role of Polymorphism in the Production ofMaterials . . . . . . . . . . . . . . . . . . . . . . 165 2.2 Crystallization and Polymorphic Transformations – Thermodynamic and Kinetic Considerations . . . . . . . . . . . . . 166 2.3 Polymorphism – Structural Considerations . . . . . . . . . . . . . . 171 3 Methodology for the Study of Crystal Polymorphism . . . . . . . . . 177 3.1 Review of Preparative Methods . . . . . . . . . . . . . . . . . . . . . 177 3.2 Review of Investigative Methods . . . . . . . . . . . . . . . . . . . . . 180 3.3 Polymorphic Systems and Polymorphic Changes – Case Studies . . . 198 4 Towards Control of Polymorphism . . . . . . . . . . . . . . . . . . . 199 4.1 The Need for Polymorphic Control . . . . . . . . . . . . . . . . . . . 199 4.2 Current Strategies and Prognosis for Crystal Engineering . . . . . . 200 5 References . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 204 Topics in Current Chemistry, Vol. 198 © Springer Verlag Berlin Heidelberg 1998
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198 Topics in Current Chemistry Edi
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Design of Organic Solids Volume Edi
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Volume Editors Prof. Dr. Edwin Webe
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VIII preface tion at an amazing lev
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Contents of Volume 196 Carbon Rich
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2 J.P. Glusker 5 Interactions of Pl
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Hydrogen-Bonded Ribbons, Tapes and
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Springer and the environment At Spr
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