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(S)-3-(Ammoniomethyl)-5-methylhexanoate (pregabalin).

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Acta Crystallographica. Section C, Crystal Structure Communications
|May 5, 2007
PubMed
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This study reveals the zwitterionic structure of a novel compound, C(8)H(17)NO(2), which self-assembles via hydrogen bonds into layered structures. These molecular layers are further stabilized by van der Waals forces.

Area of Science:

  • Crystallography
  • Supramolecular Chemistry
  • Organic Chemistry

Background:

  • Understanding molecular self-assembly is crucial for designing advanced materials.
  • Zwitterions, with their distinct charge distribution, offer unique properties for self-organization.

Purpose of the Study:

  • To elucidate the crystal structure and self-assembly mechanism of the title compound, C(8)H(17)NO(2).
  • To investigate the intermolecular interactions driving the formation of layered structures.

Main Methods:

  • Single-crystal X-ray diffraction analysis.
  • Analysis of hydrogen bonding networks (N+-H...O- and C-H...O-).
  • Identification of stabilizing interactions (van der Waals forces).

Main Results:

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  • The title compound exists as a zwitterion with a propeller conformation.
  • Molecules self-assemble into hydrogen-bonded layers parallel to the ab crystallographic plane.
  • These layers stack along the c axis, stabilized by van der Waals interactions.

Conclusions:

  • The study provides detailed insights into the crystal engineering of zwitterionic compounds.
  • The observed self-assembly mechanism highlights the importance of hydrogen bonding and van der Waals forces in supramolecular architecture.
  • This work contributes to the fundamental understanding of molecular organization in the solid state.