A comparison of the crystal packing in benzene with the geometry seen in crystalline cyclophane-benzene complexes: guidelines for rational receptor design

Self-recognition in crystalline benzene is compared with the recognition of benzene in inclusion complexes of three cyclophane receptors. It is shown that the structural organization of aromatic rings, which determines the packing in the molecular crystal and the binding geometry in the preorganized cavity of the cyclophane host molecules, follows the same principles. It is concluded that the examination of the spatial requirements of the aromatic-aromatic interaction motifs found in crystals should allow one to design host bonding skeletons with high binding selectivity and affinity for a specific aromatic guest.

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