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Directional Aspects of Intermolecular Interactions

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Design of Organic Solids

Part of the book series: Topics in Current Chemistry ((TOPCURRCHEM,volume 198))

Abstract

Directional intermolecular interactions can be found by statistical analyses of the surroundings of functional groups in all crystal structures containing them. The most notable such interaction is the hydrogen bond, which, if strong as between OH or NH groups and oxygen or nitrogen acceptors, is approximately linear. This provides an important means of aligning molecules together. Analogous but weaker interactions described here are C-H...O, F...H and H... π, and also those between C-S-C groups and electrophiles or nucleophiles. Some directionality can also be identified in aromatic-aromatic interactions. Metal ion coordination can, in certain instances, also have a directional component, particularly if the coordination geometry is inflexible, as for the octahedral binding of divalent magnesium. The geometries of interactions of metal ions with various functional groups in proteins are described, and in many cases they are more rigid than the analogous interaction involving a hydrogen bond. The emerging use of crystal surfaces as probes of molecular recognition is then discussed. Finally some examples of molecular recognition in biological macromolecules are given; these stress the importance of pattern recognition in hydrogen bonding, together with the significance of weaker interactions.

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  1. The Institute for Cancer Research, The Fox Chase Cancer Center, 7701 Burholme Avenue, Philadelphia, PA, 19111, USA

    Jenny P. Glusker

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  1. Jenny P. Glusker
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  1. Institut für Organische Chemie, Technische Universität Bergakademie Freiberg, Leipziger Straße 29, 09596, Freiberg/Sachsen, Germany

    Edwin Weber

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Glusker, J.P. (1998). Directional Aspects of Intermolecular Interactions. In: Weber, E., et al. Design of Organic Solids. Topics in Current Chemistry, vol 198. Springer, Berlin, Heidelberg. https://doi.org/10.1007/3-540-69178-2_1

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