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

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Supramolecular Synthons and Pattern Recognition 95 83. Hulliger J, Rogin P, Quintel A, Rechsteiner P, König O, Wübbenhorst M (1997) Adv Mater 9:662 84. Corey EJ, Barnes-Seeman D, Lee TW (1997) Tetrahedron Lett 38:1699 85. Pan F, Wong MS, Gramlich V, Brosshard C, Günter P (1996) Chem Comm 1557 86. Hoss R, König O, Kramer-Hoss V, Berger U, Rogin P, Hulliger J (1996) Angew Chem Int Ed Engl 35:2204 87. Navon O, Bernstein J, Khodorkovsky V (1997) Angew Chem Int Ed Engl 36:601 88. Carlucci L, Ciani G, Gudenberg DWv, Proserpio DM, Sironi A (1997) Chem Commun 631 89. Michaelides A, Skoulika S, Kiritsis V, Raptopoulou C, Terzis A (1997) J Chem Res (S) 204 90. Kräutler B, Müller T, Maynollo J, Gruber K, Kratky C, Ochsenbein P, Schwarzenbach D, Bürgi H-B (1996) Angew Chem Int Ed Engl 35:1204 91. Rowland RS (1995) Am Cryst Assoc Abstr 23:63 92. Thalladi VR, Nangia A, Desiraju GR (1997) unpublished results 93. Steiner T, Starikov EB, Amado AM, Teixeira-Dias JJC (1995) J Chem Soc Perkin Trans 2 1321 94. Madhavi NNL, Nangia A, Desiraju GR (1997) unpublished results 95. Brock CP, Duncan LL (1994) Chem Mater 6:1307
Hydrogen-Bonded Ribbons, Tapes and Sheets as Motifs for Crystal Engineering Rosa E. Meléndez · Andrew D. Hamilton Department of Chemistry, Yale University, New Haven CT 06520–8107, USA. E-mail: ahamilton@ursula.yale.chem.edu The design of new architectures for the purpose of crystal engineering has generated great interest in recent years. In particular, organic compounds have been the focus of many studies due to the presence of functional groups that can form strong and stable intermolecular interactions. Therefore, recognizing geometry and functionality at the molecular level has relevant implications in the design of supramolecular patterns. These patterns in turn can be translated to physical or chemical properties in a solid. This article is a presentation of compounds that have been designed for the purpose of molecular recognition and crystal engineering. In particular our focus will be directed towards organic structures based on the tape, ribbon, and sheet motifs. Several approaches in the design of functional solids will be presented, emphasizing the use of certain complementary intermolecular interactions for this purpose. It is not our attempt to define all concepts used for crystal engineering, but to present recent advances in this field. Keywords: Crystal engineering, Molecular recognition, Hydrogen bonding, Tapes, Sheets. 1 Introduction . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 97 2 Crystal Engineering and Molecular Recognition . . . . . . . . . . . 98 2.1 Strategies for Crystal Engineering . . . . . . . . . . . . . . . . . . . . 99 2.2 Patterns in Crystal Engineering: Tapes, Ribbons, and Sheets . . . . . 100 3 Hydrogen Bonding . . . . . . . . . . . . . . . . . . . . . . . . . . . . 102 3.1 Carboxylic Acids . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 105 3.2 Amides . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 112 3.3 Other Strong Hydrogen Bonds . . . . . . . . . . . . . . . . . . . . . . 120 3.4 Weak Interactions . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 122 4 Conclusion . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 127 5 References . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 127 1 Introduction Traditional synthetic chemistry is based upon the controlled formation and cleavage of covalent bonds. However, complicated nanoscale systems would be extremely difficult to synthesize using traditional covalent methods. As a result, 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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4 J.P. Glusker Perturbations to the
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6 J.P. Glusker 2.1 Sources of Cryst
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8 J.P. Glusker other induced, will
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10 J.P. Glusker The forces here hav
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12 J.P. Glusker lographic structure
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14 J.P. Glusker a c Fig. 6 a - c. D
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16 J.P. Glusker hydrogen bond H◊
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18 J.P. Glusker Fig. 9. Citric acid
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20 J.P. Glusker peptide plane and a
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22 J.P. Glusker 4.5 F◊◊◊H Int
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24 J.P. Glusker rine-containing com
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26 J.P. Glusker Fig. 17. The packin
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28 J.P. Glusker bind to a metal ion
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30 J.P. Glusker As for carboxylate
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32 J.P. Glusker Fig. 24. The magnes
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34 J.P. Glusker structures of magne
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36 J.P. Glusker b a Fig. 28 a, b. A
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38 J.P. Glusker Fig. 30. Complexati
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40 J.P. Glusker 7.1 Descriptions of
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42 J.P. Glusker Fig. 34. Glycine cr
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148 Y. Aoyama are intriguing guests
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150 Y. Aoyama The tuning or enginee
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152 Y. Aoyama Fig. 16. Binding isot
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154 Y. Aoyama The desorption of the
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156 Y. Aoyama Fig. 17. Suggested me
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158 Y. Aoyama 5 Concluding Remarks
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160 Y. Aoyama 4. Hölderich W, Hess
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Crystalline Polymorphism of Organic
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Author Index Volumes 151-198 Author
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Author Index Volumes 151 - 198 2 1
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Author Index Volumes 151 - 198 213
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Author Index Volumes 151 - 198 2 ]
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Springer and the environment At Spr
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