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Packing in three cyclooctitol acetates.

Goverdhan Mehta1, Saikat Sen, Kotapalli Pallavi

  • 1Department of Organic Chemistry, Indian Institute of Science, Bangalore 560 012, Karnataka, India. gm@orgchem.iisc.ernet.in

Acta Crystallographica. Section C, Crystal Structure Communications
|December 7, 2007
PubMed
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Three cyclooctitol derivatives were studied, revealing their cyclooctane ring conformation closely resembles the boat-chair form. Molecular packing involves weak hydrogen bonds and van der Waals forces.

Area of Science:

  • Organic Chemistry
  • Stereochemistry
  • Crystallography

Background:

  • Cyclooctitols are eight-membered cyclic polyols with diverse stereoisomers.
  • Acetate and acetonide derivatives are commonly synthesized for structural analysis.
  • Conformational analysis of cyclooctane rings is crucial for understanding their chemical properties.

Purpose of the Study:

  • To synthesize and characterize three cyclooctitol derivatives.
  • To investigate the conformational preferences of the cyclooctane ring in these derivatives.
  • To analyze the intermolecular interactions governing crystal packing.

Main Methods:

  • Synthesis of tetraacetate and regioisomeric acetonide triacetate derivatives.
  • X-ray crystallography for structural determination.

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  • Conformational analysis based on determined structures.

    • Main Results:

    • Three cyclooctitol derivatives were successfully prepared and structurally elucidated.
    • The cyclooctane ring in all three compounds adopts a conformation closely related to the boat-chair form.
    • Crystal structures are stabilized by weak C-H...O hydrogen bonds and van der Waals forces.

    Conclusions:

    • The boat-chair conformation is a preferred conformation for these cyclooctitol derivatives.
    • Intermolecular interactions play a significant role in the solid-state arrangement of these molecules.
    • This study provides insights into the stereochemistry and structural behavior of cyclooctitol derivatives.