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Phenolphthalein and 3',3"-dinitrophenolphthalein

L J Fitzgerald1, R E Gerkin

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

Acta Crystallographica. Section C, Crystal Structure Communications
|May 30, 1998
PubMed
Summary
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This study details the crystal structures of phenolphthalein and dinitrophenolphthalein, revealing distinct hydrogen bonding patterns. Phenolphthalein exhibits chain-like hydrogen bonds, while dinitrophenolphthalein forms both chains and cyclic dimers.

Area of Science:

  • Crystallography
  • Chemical Physics
  • Molecular Structure

Background:

  • Phenolphthalein is a widely used pH indicator.
  • Understanding the solid-state structure of organic molecules is crucial for predicting their properties.
  • Hydrogen bonding plays a significant role in molecular self-assembly and crystal packing.

Purpose of the Study:

  • To elucidate the crystal structures of phenolphthalein and 3',3"-dinitrophenolphthalein.
  • To analyze and compare the hydrogen bonding networks in both compounds.
  • To investigate the influence of nitro group substitution on crystal packing and hydrogen bonding.

Main Methods:

  • Single-crystal X-ray diffraction was employed to determine the crystal structures.
  • Analysis of intermolecular interactions, including hydrogen bonds (O-H...O and C-H...O), was performed.

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  • Comparison of crystallographic data (space group, unit cell parameters) between the two compounds.

    • Main Results:

    • Phenolphthalein crystallized in the noncentrosymmetric space group Pna2(1) with two inequivalent molecules, forming extensive chains of hydrogen bonds.
    • 3',3"-Dinitrophenolphthalein crystallized in the centrosymmetric space group Pbcn with one molecule per asymmetric unit, exhibiting both chain-like and cyclic hydrogen bonding (dimers).
    • Both structures displayed significant C-H...O interactions, attributed to an excess of oxygen acceptor atoms over donors.

    Conclusions:

    • The crystal structure of phenolphthalein is characterized by non-cyclic hydrogen bonding chains.
    • Dinitrophenolphthalein displays a more complex hydrogen bonding network, including cyclic dimers, due to nitro group substitution.
    • The study highlights the impact of chemical modification on molecular self-assembly in the solid state.