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Thiodicarb

H L Ammon1, R J Seymour, W M Huffman

  • 1Department of Chemistry and Biochemistry, University of Maryland, College Park 20742, USA.

Acta Crystallographica. Section C, Crystal Structure Communications
|August 15, 1995
PubMed
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This study examines the structure of a biscarbamate insecticide, Dimethyl N,N'-[thiobis(methyliminocarbonyloxy)] bis-(ethanimidothiolate). Molecular geometry optimization suggests crystal packing influences its observed non-planar structure.

Area of Science:

  • Chemical crystallography
  • Molecular modeling
  • Insecticide chemistry

Background:

  • Sulfenylated biscarbamate insecticides represent a class of chemical agents.
  • Understanding the molecular structure of insecticides is crucial for their development and application.
  • Dimethyl N,N'-[thiobis(methyliminocarbonyloxy)] bis-(ethanimidothiolate) is a specific example within this class.

Purpose of the Study:

  • To elucidate the three-dimensional molecular structure of Dimethyl N,N'-[thiobis(methyliminocarbonyloxy)] bis-(ethanimidothiolate).
  • To investigate the conformational preferences of the molecule in both crystalline and isolated states.
  • To compare structural parameters with related carbamate insecticides.

Main Methods:

  • X-ray crystallography was used to determine the solid-state structure.

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  • Semi-empirical quantum chemical calculations were employed for geometry optimization of the isolated molecule.
  • Analysis of bond lengths, bond angles, and molecular symmetry.

    • Main Results:

    • The crystal structure reveals an approximate twofold axis of symmetry through the central sulfur atom.
    • One of the two molecular arms exhibits non-planarity in the crystal lattice.
    • Geometry optimization indicates a preference for a planar conformation of both arms in isolation.
    • Observed bond lengths and angles are comparable to those in methomyl.

    Conclusions:

    • Crystal packing forces likely induce the non-planarity observed in one arm of the molecule.
    • The structural findings provide insights into the conformational behavior of sulfenylated biscarbamate insecticides.
    • Structural similarities to methomyl may suggest related modes of action or synthetic strategies.