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

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Supramolecular Synthons and Pattern Recognition 69 Scheme 5 27 28 29 a b Fig. 2 a, b. O-H◊◊◊N (i), N-H◊◊◊O (ii), C-H◊◊◊O (iii) and N-H◊◊◊p (iv) hydrogen bonds in the crystal structures of: a 2-aminophenol 28; b 3-aminophenol 29 [35]
70 A. Nangia · G.R. Desiraju -NH 2 group similarly donates and accepts a strong hydrogen bond with two different molecules of 28. The second H-atom participates in the N-H◊◊◊p hydrogen bond with a third molecule of 28. The hydrogen bonding array in 3-aminophenol 29 is similar to 28. A tetrahedral environment around O- and N-atoms is maintained in both structures, but unlike in 27 it is not exclusively of the strong type. The reason for the “anomalous” structures of 2- and 3-aminophenols compared with the “normal” structures of 4-aminophenol is understood in terms of the need to attain herringbone or “T”-shaped geometry of the phenyl rings in the two structures. The origin of the weaker N-H◊◊◊p and C-H◊◊◊O hydrogen bonds is then the herringbone geometry of the phenyl rings which makes the heteroatoms inaccessible for the formation of conventional N-H◊◊◊O hydrogen bonds. The preference for two weak instead of one strong hydrogen bond is caused by the optimisation of the herringbone interactions and this is identified as the primary structural effect in these compounds. In summary, simple molecules can have complex crystal structures and the relationship between molecular and crystal structures can accordingly be difficult to delineate. The above examples illustrate that connections between molecular and crystal structures are straightforward or difficult depending on whether there is insulation or interference between the different sets of significant intermolecular interactions. Thus, in 4-aminophenol, the crystal structure retains a high degree of fidelity to other hydroxy-amino systems described by Ermer because the competing herringbone and hydrogen bonding interactions are effectively insulated. In 2- and 3-aminophenols, however, the structure determining interactions interfere with one another and this leads to unexpected crystal structures. Hanessian’s compounds are somewhat less problematic because they do not contain aromatic groups. Unfortunately, it is often difficult to anticipate from a casual inspection of the molecular structure when such insulation will or will not be present. This then is a major problem in crystal engineering; indeed it is the problem, and at its heart lies our inability to predict accurately the supramolecular (crystal) structure of an arbitrary molecule from its molecular structure. 4.2 Goals and Challenges The “supramolecular Everest” of predicting the crystal structure of any given molecule is as challenging and formidable a task today as the total syntheses of vitamin B 12, gingkolide or palytoxin were in earlier times (Table 1). The subject of supramolecular synthesis is in its infancy and probably at the same stage of development as target oriented synthesis was in the 1960s. A set of empirical chemical principles for the solid state assembly of molecules has been formulated but its utility in the construction of complex architectures is yet to be completely demonstrated. This is one of the major goals of current crystal engineering strategies.
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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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Hydrogen-Bonded Ribbons, Tapes and
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132 Y. Aoyama 4 Catalysis . . . . .
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134 Y. Aoyama 2.2 Symmetry-Controll
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136 Y. Aoyama A trigonal centre is
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138 Y. Aoyama 18 19 Fig. 5. 2D net
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140 Y. Aoyama 24 ded (O-H◊◊◊O
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142 Y. Aoyama 2.4 Interaction-Suppo
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144 Y. Aoyama In the presence of a
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146 Y. Aoyama clusion compounds (se
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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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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 ]
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Springer and the environment At Spr
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198 Topics in Current Chemistry Editorial Board: A. de Meijere KN ...

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