Stibinin
{{Chembox
|ImageFileL1 = Stibabenzene.svg
|ImageSizeL1 = 100px
|ImageFileR1=Stibinin Ball and Stick.png
|ImageSizeR1=150px
|ImageCaptionR1=The white balls represent hydrogens, the light gray balls represent carbons, and the dark gray ball represents antimony
|PIN=Stibinine
|OtherNames=Antimonin; Stibabenzene
|Section1={{Chembox Identifiers
|CASNo = 289-75-8
|ChemSpiderID = 119914
|PubChem = 136137
|StdInChI=1S/C5H5.Sb/c1-3-5-4-2;/h1-5H;
|StdInChIKey = JRKNFVZITCJKDC-UHFFFAOYSA-N
|SMILES = C1=CC=[Sb]C=C1
}}
|Section2={{Chembox Properties
|C=5|H=5|Sb=1
}}
}}
Stibinin, also known as stibabenzene, is an organic chemical compound. Stibinin has the chemical formula {{chem2|C5H5Sb|auto=1}}. 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.
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.{{Cite journal|last1=Ashe|first1=Arthur J.|last2=Fang|first2=Xiangdong|last3=Fang|first3=Xinggao|last4=Kampf|first4=Jeff W.|date=December 2001|title=Synthesis of 1,2-Dihydro-1,2-azaborines and Their Conversion to Tricarbonyl Chromium and Molybdenum Complexes|journal=Organometallics|language=en|volume=20|issue=25|pages=5413–5418|doi=10.1021/om0106635|issn=0276-7333}}
:{{chem2|C5H4 + Bu2SnH2 -> C13H24Sn}}
:File:Stibinin Reaction Schematic 1.png{{clear-left}}
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.{{Cite journal|last=Ashe|first=Arthur J.|date=December 1971|title=Stibabenzene|journal=Journal of the American Chemical Society|language=EN|volume=93|issue=24|pages=6690–6691|doi=10.1021/ja00753a069|issn=0002-7863}}
:{{chem2|C13H24Sn + SbCl3 -> C5H6SbCl}}
:File:Stibinin Reaction Schematic 2.png{{clear-left}}
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.
:{{chem2|C5H6SbCl + DBN -> C5H6Sb}}
:File:Stibinin Reaction Schematic 3.png{{clear-left}}
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.{{Cite journal|last=Ashe|first=Arthur J.|date=February 2016|title=The Route to Phosphabenzene and Beyond|journal=European Journal of Inorganic Chemistry|language=en|volume=2016|issue=5|pages=572–574|doi=10.1002/ejic.201600007|issn=1434-1948|url=https://deepblue.lib.umich.edu/bitstream/2027.42/117476/1/572_ftp.pdf|hdl=2027.42/117476|s2cid=101713336 |hdl-access=free}}
See also
- 6-membered aromatic rings with one carbon replaced by another group: borabenzene, silabenzene, germabenzene, stannabenzene, pyridine, phosphorine, arsabenzene, stibabenzene, bismabenzene, pyrylium, thiopyrylium, selenopyrylium, telluropyrylium
File:Bond lengths of group 15 heterobenzenes and benzene.svg, phosphorine, arsabenzene, stibabenzene, and bismabenzene{{Clarification needed|Bond lengths are in picometers, angstroms, nanometers, microinches, femtofoots, potatoes, frogs, my gramma?!|date=August 2022}}]]
References
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