Stannabenzene
{{Chembox
|Verifiedfields = changed
|verifiedrevid = 470470486
|ImageFileL1 = Stannabenzene.svg
|ImageSizeL1 = 80px
|ImageFileR1 = Stannabenzene-Spartan-MP2-3D-balls.png
|ImageSizeR1 = 120px
|ImageFile2 = Stannabenzene-Spartan-MP2-3D-SF.png
|ImageSize2 = 120px
|PIN = Stannine
|OtherNames = Stannin
|Section1={{Chembox Identifiers
|ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}
|ChemSpiderID = 20137777
|StdInChI_Ref = {{stdinchicite|correct|chemspider}}
|StdInChI = 1S/C5H5.Sn.H/c1-3-5-4-2;;/h1-5H;;/b3-1?,5-4-;;
|StdInChIKey_Ref = {{stdinchicite|correct|chemspider}}
|StdInChIKey = USOBSXNBGFXQQW-RJPIHQCFSA-N
|CASNo_Ref = {{cascite|changed|??}}
|CASNo = 289-78-1
|PubChem = 119197
|SMILES = [H][Sn]1=CC=CC=C1
}}
|Section2={{Chembox Properties
| C=5 | H=6 | Sn=1
}}
}}
Stannabenzene (C5H6Sn) is the parent representative of a group of organotin compounds that are related to benzene with a carbon atom replaced by a tin atom. Stannabenzene itself has been studied by computational chemistry,{{cite journal | doi = 10.1016/j.theochem.2009.10.038 |author1=Ebrahimi, Arash Afshar |author2=Ghiasi, Reza |author3=Foroutan-Nejad, Cina | title = Topological characteristics of the ring critical points and the aromaticity of groups IIIA to VIA hetero-benzenes | journal = Journal of Molecular Structure: THEOCHEM | year = 2010 | volume = 941 | issue = 1–3 | pages = 47–52}} but has not been isolated.
Stable derivatives of stannabenzene
Stable derivatives of stannabenzene have been isolated. The 2-stannanaphthalene depicted below is stable in an inert atmosphere at temperatures below 140 °C.{{cite journal | last1 = Mizuhata | first1 = Yoshiyuki | last2 = Sasamori | first2 = Takahiro | last3 = Takeda | first3 = Nobuhiro | last4 = Tokitoh | first4 = Norihiro | title = A Stable Neutral Stannaaromatic Compound: Synthesis, Structure and Complexation of a Kinetically Stabilized 2-Stannanaphthalene | journal = Journal of the American Chemical Society | volume = 128 | pages = 1050–1 | year = 2006 | doi = 10.1021/ja057531d | issue = 4 | pmid = 16433501}} The tin to carbon bond in this compound is shielded from potential reactants by two very bulky groups, one tert-butyl group and the even larger 2,4,6-tris[bis(trimethylsilyl)methyl]phenyl or Tbt group. The two Sn-C bonds have bond lengths of 202.9 and 208.1 pm which are shorter than those for Sn-C single bonds (214 pm) and comparable to that of known Sn=C double bonds (201.6 pm). The C-C bonds show little variation with bond lengths between 135.6 and 144.3 pm signaling that this compound is aromatic.
:File:stannabenzene derivative.svg{{clear left}}
Tbt-substituted 9-stannaphenanthrene was reported in 2005.Generation of 9-Stannaphenanthrene and Its Reactivities Yoshiyuki Mizuhata, Nobuhiro Takeda, Takahiro Sasamori and Norihiro Tokitoh Chemistry Letters Volume 34 Number 8 Year 2005 Page 1088 {{doi|10.1246/cl.2005.1088}} At room temperature it forms the [4+2] cycloadduct.
Tbt-substituted stannabenzene was reported in 2010.Generation of Stannabenzenes and Their Properties Yoshiyuki Mizuhata, Naoya Noda, and Norihiro Tokitoh Organometallics, 2010, 29 (21), pp 4781–4784 {{doi| 10.1021/om100382n}} At room-temperature it quantitatively forms the DA dimer.
:File:Stannabenzene Mizuhata 2010.svg (step 2), NBS (step 3), LDA (step 4) ]]{{clear left}}
See also
- 6-membered aromatic rings with one carbon replaced by another group: borabenzene, silabenzene, germabenzene, stannabenzene, pyridine, phosphorine, arsabenzene, bismabenzene, pyrylium, thiopyrylium, selenopyrylium, telluropyrylium