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Serendipity and four polymorphic structures of benzidine, C12H12N2.

Michal Rafilovich1, Joel Bernstein

  • 1Department of Chemistry, Ben-Gurion University of the Negev, P.O. Box 653, Be'er Sheva 84105, Israel.

Journal of the American Chemical Society
|September 14, 2006
PubMed
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Researchers discovered four new crystal forms (polymorphs) of benzidine, a compound used in chemical synthesis. These polymorphs exhibit unusual molecular arrangements and were previously unreported, expanding knowledge of benzidine

Area of Science:

  • Crystal Engineering
  • Materials Science
  • Solid-State Chemistry

Background:

  • Benzidine is a bifunctional molecule with potential as a hydrogen-bond donor.
  • Co-crystal formation is a key strategy in materials design.
  • No crystal structure for benzidine had been reported in the Cambridge Structural Database as of November 2005.

Purpose of the Study:

  • To search for co-crystals of benzidine.
  • To characterize the solid-state forms of benzidine.
  • To investigate the structural diversity of benzidine polymorphs.

Main Methods:

  • Single-crystal X-ray diffraction to determine molecular structures.
  • Polymorph screening under high-temperature (HT) conditions.
  • Spectroscopic analysis (e.g., IR, Raman).

Related Experiment Videos

  • Thermodynamic characterization.

    • Main Results:

    • Four novel polymorphs of benzidine were identified and structurally characterized.
    • These polymorphs exhibit unusual numbers of molecules in the asymmetric unit (Z' = 1.5, 3, and 4.5).
    • Two forms (I and IV) with Z' = 4.5 are visually indistinguishable.
    • Molecular planarity varies depending on the crystallographic site (inversion center).

    Conclusions:

    • The study reveals significant, previously unreported structural complexity in benzidine.
    • The identified polymorphs challenge existing structural databases.
    • Understanding these polymorphs is crucial for controlling benzidine's solid-state properties and reactivity.