Carbonyl selenide

Carbonyl selenide
Names
Preferred IUPAC name
Selanylidenemethanone
Identifiers
3D model (JSmol)
ChemSpider
  • InChI=1S/COSe/c2-1-3
    Key: RQZJHKMUYSXABM-UHFFFAOYSA-N
  • [Se]=C=O
Properties
COSe
Molar mass 106.981 g·mol−1
Appearance Colorless gas
Odor Unpleasant
Boiling point −22 °C (−8 °F; 251 K)
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).

Carbonyl selenide is a chemical compound with the chemical formula O=C=Se. It is a linear molecule that is primarily of interest for research purposes.

Properties

Carbonyl selenide is a colorless gas with an unpleasant odor.[1] Although the compound is quite stable, its solutions gradually revert to elemental selenium and carbon monoxide.[2]

Synthesis and reactions

Carbonyl selenide can be produced by treating selenium with carbon monoxide in the presence of amines.[3]

It is used in organoselenium chemistry as a means of incorporating selenium into organic compounds, e.g. for the preparation of selenocarbamates (O-selenocarbamates R−O−C(=Se)−NR'R" and Se-selenocarbamates, R−Se−C(=O)−NR'R", where R is organyl and R' and R" are any group, typically H or organyl).[3]

References

  1. ^ Pearson, T. G.; Robinson, P. L. (1932), "Carbonyl selenide. Part I. Preparation and physical properties.", Journal of the Chemical Society (Resumed): 652–660, doi:10.1039/jr9320000652
  2. ^ Sonoda, Noboru (1993). "Selenium assisted carbonylation with carbon monoxide" (PDF). Pure and Applied Chemistry. 65 (4). Great Britain: 699–706. doi:10.1351/pac199365040699. S2CID 96262544.
  3. ^ a b Banert, Klaus (2014). Science of Synthesis Knowledge Updates 2014. Vol. 3. Georg Thieme Verlag. ISBN 9783131763112.