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Materials Synthesis and Characterization pp 19–60Cite as

Diastereomeric Discrimination: Structural Aspects

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Abstract

Study of crystal and molecular structures offers detailed pictures of intermolecular interactions in the solid state. These serve as exemplars for the understanding of intermolecular interactions in the disordered phases of the liquid state and solution. Properties and reactivity of chemical species and systems are axiomatically related to their structure. One of the most important and active areas of structural study concerns molecular complexation. The concept of structural complementarity underlies a wide range of chemical and biological topics embracing antigen-antibody interactions, enzyme-substrate and enzyme-inhibitor interactions, and host-guest relationships, many with potential and application among the separation sciences. One of the oldest of the physical separation methods with a history of practical exploitation is the use of diastereomeric complexes for (partial) resolution of enantiomeric mixtures (Pasteur, 1853). The traditional method takes advantage of the differential solubility of the complexes in an appropriately chosen solvent. Since the less-soluble phase separates from solution usually as a crystalline solid leaving the more-soluble phase in solution, the less-soluble phase is a molecular assembly with macroscopic properties palpably different from its diastereomeric relative. And so it is not surprising that together with the lower solubilities, one finds higher heats of solution, heats of fusion and fusion points for the less-soluble phases (Jacques, Collet & Wilen, 1981).

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Authors and Affiliations

  1. Department of Chemistry, Mississippi College, Clinton, MS, 39058, USA

    Edward J. Valente, Gerard Ruggiero & Christopher W. Miller

  2. Department of Chemistry, Jackson State University, Jackson, MS, 39217, USA

    Jeffrey D. Zubkowski

  3. Department of Physical and Structural Chemistry, SmithKline Beecham Pharmaceuticals, King of Prussia, PA, 19401, USA

    Drake Eggleston

Authors
  1. Edward J. Valente
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  2. Gerard Ruggiero
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  3. Christopher W. Miller
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  4. Jeffrey D. Zubkowski
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  5. Drake Eggleston
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Editor information

Editors and Affiliations

  1. Lawrence Berkeley National Laboratory, Berkeley, California, USA

    Dale L. Perry

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© 1997 Springer Science+Business Media New York

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Valente, E.J., Ruggiero, G., Miller, C.W., Zubkowski, J.D., Eggleston, D. (1997). Diastereomeric Discrimination: Structural Aspects. In: Perry, D.L. (eds) Materials Synthesis and Characterization. Springer, Boston, MA. https://doi.org/10.1007/978-1-4899-0145-3_2

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  • DOI: https://doi.org/10.1007/978-1-4899-0145-3_2

  • Publisher Name: Springer, Boston, MA

  • Print ISBN: 978-1-4899-0147-7

  • Online ISBN: 978-1-4899-0145-3

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