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8-Aminocaprylic acid

A J Dobson1, R E Gerkin

  • 1Department of Chemistry, Ohio State University, Columbus 43210, USA.

Acta Crystallographica. Section C, Crystal Structure Communications
|September 18, 1998
PubMed
Summary
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This study details the crystal structure of 8-aminooctanoic acid, revealing a zwitterionic form with an ordered hydrogen bonding network. The findings highlight complex intermolecular interactions and chain formation in this amino acid derivative.

Area of Science:

  • Crystallography
  • Chemical Physics
  • Molecular Biology

Background:

  • 8-aminooctanoic acid is a valuable molecule with potential applications in various scientific fields.
  • Understanding its solid-state structure is crucial for predicting its chemical behavior and designing new materials.
  • Previous structural data may be limited, necessitating detailed crystallographic analysis.

Purpose of the Study:

  • To determine the precise crystal structure of 8-aminooctanoic acid.
  • To elucidate the intermolecular interactions, particularly hydrogen bonding, in its zwitterionic form.
  • To characterize the network formed by these hydrogen bonds and identify predominant structural motifs.

Main Methods:

  • Single-crystal X-ray diffraction was employed to obtain the crystallographic data.

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  • The crystal structure was solved and refined using standard crystallographic software.
  • Analysis of hydrogen bond geometry (distances and angles) was performed.

    • Main Results:

    • 8-aminooctanoic acid crystallizes in the centrosymmetric space group P2(1)/n as a zwitterion.
    • Three hydrogen atoms involved in hydrogen bonding are found to be ordered.
    • Five intermolecular N-H...O hydrogen bonds were identified, with distances ranging from 2.752 to 3.258 Å and angles from 131 to 165 degrees.
    • Each molecule participates in ten hydrogen bonds, linking it to six neighbors.
    • A complex hydrogen bond network, predominantly featuring chains, was observed.

    Conclusions:

    • The crystal structure of 8-aminooctanoic acid is characterized by a well-defined zwitterionic form and an extensive hydrogen bonding network.
    • The ordered nature of the hydrogen atoms and the specific geometry of the hydrogen bonds dictate the formation of complex chain structures.
    • These findings provide fundamental insights into the molecular assembly of 8-aminooctanoic acid, relevant for materials science and biochemistry.