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1,4-dimethoxy-2-naphthoic acid

A C Blackburn1, R E Gerkin

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

Acta Crystallographica. Section C, Crystal Structure Communications
|November 18, 1997
PubMed
Summary
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This study reveals cyclic dimer hydrogen bonding in a C13H12O4 crystal structure. The hydrogen bonding is similar to 2-naphthoic acid, with methoxyl groups having minimal impact.

Area of Science:

  • Crystallography
  • Supramolecular Chemistry
  • Organic Chemistry

Background:

  • Hydrogen bonding plays a crucial role in molecular self-assembly and crystal engineering.
  • Understanding hydrogen bonding patterns in organic molecules informs the design of materials with specific properties.
  • The influence of substituent groups on hydrogen bonding requires detailed structural investigation.

Purpose of the Study:

  • To elucidate the crystal structure and hydrogen bonding characteristics of the title compound, C13H12O4.
  • To investigate the role of methoxyl groups in modulating hydrogen bonding interactions.
  • To compare the observed hydrogen bonding with that of related compounds like 2-naphthoic acid.

Main Methods:

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

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  • The crystal lattice was analyzed to identify hydrogen bonding motifs.
  • Structural comparison with 2-naphthoic acid was performed.

    • Main Results:

    • The title compound, C13H12O4, crystallizes in the centrosymmetric space group P2(1)/c.
    • A cyclic dimer hydrogen bonding motif, centered on an inversion center, was observed.
    • The carboxylic hydrogen atom was found to be disordered over two half-occupancy sites.
    • Methoxyl groups showed minimal influence on the hydrogen bonding, which closely resembles that in 2-naphthoic acid.

    Conclusions:

    • The crystal structure of C13H12O4 features robust cyclic dimer hydrogen bonding.
    • The observed hydrogen bonding pattern is largely independent of the methoxyl substituents.
    • The findings provide insights into structure-property relationships in related organic acids.