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

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102 R.E. Meléndez · A.D. Hamilton Fig. 3. Tape structure formed by p-nitroaniline (1) component and the dashed lines represent intermolecular interactions. In terms of crystal engineering, the ribbon motif is less appealing since at this stage it is the more complex to understand and control. Tapes and ribbons have been of interest in crystal engineering due to various applications in material sciences. Stabilization of the translation of molecules through intermolecular forces in a solid can generate polarity, which is a necessary condition for a number of physical properties. For example, small-molecule nitroaniline compounds show preference for a motif that involves one amino proton associating with both oxygens of a nitro group, leading to the formation of a tape structure (Fig. 3). In particular, p-nitroaniline (1) has been studied for its non-linear optical properties [21]. The sheet archetype has received much interest because of its potential to generate structural patterns that contain voids, which may in turn have applications in the area of zeolitic materials. Trimesic acid (2) (Fig. 9) has been extensively studied for this purpose [22]. However, Etter and Frankenbach have been able to form polar sheets when 2,5-dinitrobenzoic acid (3) and 4-aminobenzoic acid (4) are cocrystallized by using the nitro-amine and carboxylic acid recognition motif (Fig. 4) [23]. We will present examples of tapes, ribbons, and sheets based on hydrogen bonding and other intermolecular interaction patterns. The use of both strong hydrogen bonding groups such as carboxylic acids and amides, as well as, weak interactions such as C-H◊◊◊O hydrogen bonds and iodo◊◊◊nitro polarization interactions will be covered. 3 Hydrogen Bonding Hydrogen bonding is without doubt the most studied intermolecular interaction, presumably due to its frequent presence in organic solids and biological molecules. Various attempts have been made to define the hydrogen bond [24, 25] and many detailed investigations of its properties have been carried out [9, 26]. Pioneering scientists such as Etter [27, 28], Leiserowitz and Schmidt [16, 17], Jeffrey and Saenger [29, 30], and Taylor and Kennard [31] have conducted extensive studies of the solid-state structures of organic compounds in a search for patterns, directionality, and strength in the occurrence of hydrogen bonding. The selectivity and directional nature of hydrogen bonding has led to its extensive use in the construction and stabilization of large non-covalently bonded molecular and supramolecular structures. Hydrogen bonds are formed when
Hydrogen-Bonded Ribbons, Tapes and Sheets as Motifs for Crystal Engineering 103 Fig. 4. Polar sheets formed by 3 and 4 3 4 a donor (D) with an available acidic hydrogen atom is brought into intimate contact with an acceptor (A) as shown in Fig. 5 [32]. The strength of different hydrogen bonds can vary from 1 kcal/mol for C-H◊◊◊O [33] interactions to 40 kcal/mol for [F-H-F] – [34, 35]. In terms of geometry, the hydrogen bond has been studied by statistical investigations [31] and by X-ray diffraction analysis [36] (see also the article by J.P. Glusker in this volume). One of the first detailed studies of hydrogen bonding patterns in the solid state was conducted by Etter. Her studies showed that functional groups display a preference for certain recognition patterns, leading to the conclusion that hydrogen bonding is not random, but controlled by the directional strength of the intermolecular interactions [27]. Thereby illustrating that hydrogen bonding can be used as a synthetic tool to affect profoundly the spatial arrangement of molecules and ions in the solid-state. Another important contribution by Etter was the development of graph sets in order to define the morphology of hydrogen bonded arrays. Recently, Bernstein et al. have expanded the approach
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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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44 J.P. Glusker bonding capabilitie
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46 J.P. Glusker 2. Non-intercalativ
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48 J.P. Glusker d Fig. 37 d. The ch
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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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