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Related Experiment Videos

Hydrogen bonding in sulfonamides.

D A Adsmond1, D J Grant

  • 1Department of Pharmaceutics, College of Pharmacy, University of Minnesota, Weaver-Densford Hall, 308 Harvard Street S.E., Minneapolis, Minnesota 55455-0343, USA. adsmondd@ferris.edu

Journal of Pharmaceutical Sciences
|December 18, 2001
PubMed
Summary
This summary is machine-generated.

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This study deciphers hydrogen-bond patterns in sulfonamide crystals using graph set notation. It reveals specific hydrogen-bonding preferences that could predict pharmaceutical solid-state structures.

Area of Science:

  • Crystal Engineering
  • Supramolecular Chemistry
  • Organic Solid-State Chemistry

Background:

  • Understanding hydrogen bonding in organic crystals is crucial for predicting solid-state properties.
  • Sulfonamides are a versatile class of compounds with significant pharmaceutical applications.
  • Graph set notation provides a standardized method for describing hydrogen-bond networks.

Purpose of the Study:

  • To analyze and describe the hydrogen-bond connectivity in 39 sulfonamide crystal structures.
  • To identify specific hydrogen-bonding preferences of donor and acceptor atoms within sulfonamide molecules.
  • To explore the potential of hydrogen-bonding patterns for predicting pharmaceutical solid-state structures.

Main Methods:

  • Utilized graph set notation to systematically analyze hydrogen-bond connectivity.

Related Experiment Videos

  • Examined 39 distinct crystal structures of sulfonamide compounds.
  • Compared hydrogen-bonding patterns across related and unrelated sulfonamide derivatives and polymorphs.

    • Main Results:

    • Identified distinct hydrogen-bonding preferences for amido and amino protons in sulfonamides.
    • Observed a dominant chain pattern with an eight-atom repeat unit formed by amino protons and sulfonyl oxygens.
    • Found varied hydrogen-bonding similarities and differences among structurally related sulfonamides and their polymorphs.

    Conclusions:

    • Hydrogen-bond connectivity in sulfonamides exhibits specific, predictable patterns.
    • Analysis of hydrogen-bonding motifs can offer predictive insights into the crystal structures of pharmaceutical solids.
    • Detailed structural studies of related compounds are valuable for understanding and predicting solid-state behavior.