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Synthon hierarchies in crystal forms composed of theophylline and hydroxybenzoic acids: Cocrystal screening via solution-mediated phase transformation

Crystal Growth and Design, ISSN: 1528-7505, Vol: 14, Issue: 10, Page: 5318-5328
2014
  • 42
    Citations
  • 0
    Usage
  • 50
    Captures
  • 0
    Mentions
  • 0
    Social Media
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Metrics Details

  • Citations
    42
    • Citation Indexes
      42
  • Captures
    50

Article Description

Theophylline, a pharmaceutical model compound, was screened for cocrystal formation using nine (di)hydroxybenzoic acids as cocrystal formers, namely, 2-, 3-, 4-hydroxybenzoic- and 2,3-, 2,4-, 2,5-, 2,6-, 3,4-, and 3,5-dihydroxybenzoic acids. The experiments were conducted using an efficient, reliable, and fast screening method based on thermodynamically driven solution-mediated phase transformation and revealed the formation of eight cocrystals and one salt. The theophylline-based solids were identified using powder and structurally characterized via single-crystal X-ray diffraction. The obtained solids are sustained by theopylline-carboxylic acid heterosynthons, in addition to both theophylline and carboxylic acid homosynthons. The results are a part of a systematic study of xanthine-alkaloid cocrystals that aims to establish synthon hierarchies in cocrystals comprised of molecules with multiple hydrogen-bonding functional groups. Structural features and synthon hierachies are discussed and compared to those in a series of published caffeine cocrystals.

Bibliographic Details

Dejan-Krešimir Bučar; Rodger F. Henry; Geoff G. Z. Zhang; Leonard R. MacGillivray

American Chemical Society (ACS)

Chemistry; Materials Science; Physics and Astronomy

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