Stibinin

Stibinin, also known as stibabenzene,[1] is an organic chemical compound. Stibinin has the chemical formula C5H5Sb. The molecule, stibinin, is a derivative of benzene, with one of the carbon atoms in the 6-membered ring replaced by an antimony (Sb) atom. Stibinin is a molecule that is considered to be an organoantimony compound due to it containing carbon, hydrogen, and antimony atoms.

Stibinin
The white balls represent hydrogens, the light gray balls represent carbons, and the dark gray ball represents antimony
Names
Preferred IUPAC name
Stibinine
Other names
Antimonin; Stibabenzene
Identifiers
3D model (JSmol)
ChemSpider
  • InChI=1S/C5H5.Sb/c1-3-5-4-2;/h1-5H;
    Key: JRKNFVZITCJKDC-UHFFFAOYSA-N
  • C1=CC=[Sb]C=C1
Properties
C5H5Sb
Molar mass 186.855 g·mol−1
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
Infobox references

Laboratory synthesis

The synthesis of stibinin can be accomplished in a three step process. The final product can be isolated, even though the molecule is highly labile. The first step of this synthesis involves the treatment of penta-1,4-diyne with dibutylstannane as shown in the figure below.[2]

C5H4 + Bu2SnH2 → C13H24Sn

The second step of the synthesis involves reacting the product of the first step, 1,1-dibutyl-1,4-dihydrostannine, with antimony trichloride, to yield 1-chloro-1-stibacyclohexa-2,5-diene.[1]

C13H24Sn + SbCl3 → C5H6SbCl

The final step of the synthesis of stibinin involves treating 1-chloro-1-stibacyclohexa-2,5-diene with a base, such as DBN, to yield the final product of stibinin.

C5H6SbCl + DBN → C5H6Sb

Similar compounds

It is noted that other benzene derivatives with one carbon replaced with a group 15 element can be synthesized via a similar synthetic pathway to that which stibinin is synthesized. The reaction of 1,1-dibutyl-1,4-dihydrostannine with arsenic trichloride, phosphorus tribromide, or bismuth trichloride can yield arsabenzene, phosphabenzene, or 1-chloro-1-bismacyclohexa-2,5-diene respectively. Treatment of 1-chloro-1-bismacyclohexa-2,5-diene with a base, such as DBN, can yield the product bismabenzene.[3]

The four different reaction pathways possible from 1,1-dibutyl-1,4-dihydrostannin to form the products arsabenzene, phosphabenzene, bismabenzene, and stibabenzene.

See also
Bond lengths and angles of benzene, pyridine, phosphorine, arsabenzene, stibabenzene, and bismabenzene

References
  1. Ashe, Arthur J. (December 1971). "Stibabenzene". Journal of the American Chemical Society. 93 (24): 6690–6691. doi:10.1021/ja00753a069. ISSN 0002-7863.
  2. Ashe, Arthur J.; Fang, Xiangdong; Fang, Xinggao; Kampf, Jeff W. (December 2001). "Synthesis of 1,2-Dihydro-1,2-azaborines and Their Conversion to Tricarbonyl Chromium and Molybdenum Complexes". Organometallics. 20 (25): 5413–5418. doi:10.1021/om0106635. ISSN 0276-7333.
  3. Ashe, Arthur J. (February 2016). "The Route to Phosphabenzene and Beyond" (PDF). European Journal of Inorganic Chemistry. 2016 (5): 572–574. doi:10.1002/ejic.201600007. hdl:2027.42/117476. ISSN 1434-1948.
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