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Related Experiment Videos

Structure of (+/-)-aminoglutethimide.

P Van Roey1, K A Bullion, Y Osawa

  • 1Medical Foundation of Buffalo Inc., NY 14203.

Acta Crystallographica. Section C, Crystal Structure Communications
|April 15, 1991
PubMed
Summary

This study details the L-shaped crystal structure of (+/-)-3-(4-Aminophenyl)-3-ethyl-2,6-piperidinedione. The arrangement of its functional groups differs between the active and less-active enantiomers, similar to phenobarbital.

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Area of Science:

  • Crystallography
  • Organic Chemistry
  • Molecular Structure

Background:

  • The molecule (+/-)-3-(4-Aminophenyl)-3-ethyl-2,6-piperidinedione is a derivative with potential biological relevance.
  • Understanding its three-dimensional structure is crucial for structure-activity relationship studies.
  • Previous structural data for similar compounds like phenobarbital provide a basis for comparison.

Purpose of the Study:

  • To determine and analyze the crystal structure of (+/-)-3-(4-Aminophenyl)-3-ethyl-2,6-piperidinedione.
  • To elucidate the molecular conformation and intermolecular interactions.
  • To compare the determined structure with that of phenobarbital.

Main Methods:

  • Single-crystal X-ray diffraction was employed to collect diffraction data.

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  • The crystal structure was solved and refined using standard crystallographic techniques.
  • Unit cell parameters and atomic coordinates were determined for the monoclinic crystal system.

    • Main Results:

    • The molecule adopts an L-shaped conformation, with distinct positioning of the p-aminophenyl and piperidinedione groups.
    • The orientation of the piperidinedione group's polar imide moiety differs between the active (+) and less-active (-) enantiomers.
    • Intermolecular interactions observed include hydrogen bonding and potential pi-cloud interactions.

    Conclusions:

    • The crystal structure of (+/-)-3-(4-Aminophenyl)-3-ethyl-2,6-piperidinedione has been elucidated.
    • Structural similarities and differences with phenobarbital were noted.
    • The observed molecular and crystal structure provides insights into the compound's stereochemistry and potential interactions.