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5-aminoisophthalic acid hemihydrate

A J Dobson1, R E Gerkin

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

Acta Crystallographica. Section C, Crystal Structure Communications
|November 10, 1998
PubMed
Summary

This study details the crystal structure of 5-ammonioisophthalate, revealing a zwitterionic form stabilized by an extensive three-dimensional hydrogen bond network. The analysis highlights the prevalence of hydrogen-bonded chains over rings in this crystalline material.

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Area of Science:

  • Crystallography
  • Materials Science
  • Chemical Physics

Background:

  • Understanding the crystalline structure of organic molecules is crucial for predicting their physical and chemical properties.
  • Zwitterionic compounds exhibit unique intermolecular interactions that influence their solid-state behavior.
  • Hydrogen bonding plays a pivotal role in the self-assembly and network formation of molecular crystals.

Purpose of the Study:

  • To determine the crystal structure of the title acid, C8H7NO4.0.5H2O.
  • To characterize the hydrogen bonding network within the crystal lattice.
  • To analyze the topology of the hydrogen bond network, comparing chains and rings.

Main Methods:

  • Single-crystal X-ray diffraction was employed to elucidate the crystal structure.

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  • The crystal structure was analyzed in the centrosymmetric space group C2/c.
  • Hydrogen bond analysis was performed using geometric criteria (distances and angles).

    • Main Results:

    • The title acid crystallized in a zwitterionic form (5-ammonioisophthalate) with a water molecule.
    • Ordered hydrogen atoms were observed in both the ammonio and carboxyl groups, participating in hydrogen bonding.
    • A 3D hydrogen bond network was identified, featuring three intermolecular N-H...O bonds and two intermolecular O-H...O bonds.
    • Analysis of hydrogen bond graphs revealed a greater abundance of chains compared to rings.

    Conclusions:

    • The crystal structure of 5-ammonioisophthalate is characterized by a robust 3D hydrogen bond network.
    • The zwitterionic nature and ordered hydrogen atoms contribute to the stability of the crystal structure.
    • The prevalence of chains over rings in the hydrogen bond network provides insights into the packing and assembly mechanisms of this compound.