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Dimethyl selenoxide.

Alexander S Filatov1, Eric Block, Marina A Petrukhina

  • 1Department of Chemistry, University at Albany, SUNY, Albany, NY 12222, USA.

Acta Crystallographica. Section C, Crystal Structure Communications
|October 8, 2005
PubMed
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Dimethyl selenoxide (DMSeO), a molecule structurally similar to DMSO, exhibits a trigonal-pyramidal form. In its solid state, DMSeO molecules form dimers and a ladder-like network through hydrogen bonds, with each oxygen atom accepting three hydrogen bonds.

Area of Science:

  • Organoselenium chemistry
  • Supramolecular chemistry
  • Crystallography

Background:

  • Dimethyl sulfoxide (DMSO) is a well-known organosulfur compound with a trigonal-pyramidal structure.
  • Organoselenium compounds are less studied but possess unique chemical properties.
  • Understanding the structural and bonding characteristics of selenium analogs is crucial for expanding chemical knowledge.

Purpose of the Study:

  • To investigate the structural properties of dimethyl selenoxide (DMSeO), the selenium analog of DMSO.
  • To elucidate the intermolecular interactions and solid-state assembly of DMSeO.
  • To compare the Se-O bond characteristics with the S-O bond in DMSO.

Main Methods:

  • Single-crystal X-ray diffraction was employed to determine the molecular and crystal structure of DMSeO.

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  • Analysis of bond distances (Se-O) and angles provided insights into molecular geometry.
  • Identification and analysis of intermolecular interactions (hydrogen bonds) were performed.

    • Main Results:

    • DMSeO adopts a trigonal-pyramidal structure, similar to DMSO.
    • The Se-O bond length in DMSeO (1.6756 Å) is longer than the S-O bond in DMSO (1.531 Å), indicating a highly polar bond.
    • In the solid state, DMSeO molecules form centrosymmetric dimers via C-H...O hydrogen bonds, which further aggregate into a ladder-like supramolecular network.
    • Each oxygen atom in DMSeO acts as an acceptor for three hydrogen bonds.

    Conclusions:

    • Dimethyl selenoxide exhibits unique solid-state packing driven by intermolecular hydrogen bonding.
    • The structural and bonding data provide valuable insights into the chemistry of organoselenium compounds.
    • DMSeO's supramolecular assembly highlights the role of weaker interactions in organizing molecular structures.