Stannabenzene

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title: "Stannabenzene" type: doc version: 1 created: 2026-02-28 author: "Wikipedia contributors" status: active scope: public tags: ["tin-heterocycles", "six-membered-rings", "hypothetical-chemical-compounds", "tin(iv)-compounds"] topic_path: "science/chemistry" source: "https://en.wikipedia.org/wiki/Stannabenzene" license: "CC BY-SA 4.0" wikipedia_page_id: 0 wikipedia_revision_id: 0

|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 = |ChemSpiderID = 20137777 |StdInChI_Ref = |StdInChI = 1S/C5H5.Sn.H/c1-3-5-4-2;;/h1-5H;;/b3-1?,5-4-;; |StdInChIKey_Ref = |StdInChIKey = USOBSXNBGFXQQW-RJPIHQCFSA-N |CASNo_Ref = |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, 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. 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|400px|thumb|left|A stable 2-stannanaphthalene derivative]]

Tbt-substituted 9-stannaphenanthrene was reported in 2005. At room temperature it forms the [4+2] cycloadduct.

Tbt-substituted stannabenzene was reported in 2010. At room-temperature it quantitatively forms the DA dimer.

:[[File:Stannabenzene Mizuhata 2010.svg|600px|thumb|left|Tbt-substituted stannabenzene synthesis. Reagents [[lithium aluminium hydride]] (step 2), [[N-Bromosuccinimide|NBS]] (step 3), [[Lithium diisopropylamide|LDA]] (step 4) ]]

References

References

  1. (2010). "Topological characteristics of the ring critical points and the aromaticity of groups IIIA to VIA hetero-benzenes". Journal of Molecular Structure: THEOCHEM.
  2. (2006). "A Stable Neutral Stannaaromatic Compound: Synthesis, Structure and Complexation of a Kinetically Stabilized 2-Stannanaphthalene". Journal of the American Chemical Society.
  3. ''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
  4. ''Generation of Stannabenzenes and Their Properties'' Yoshiyuki Mizuhata, Naoya Noda, and Norihiro Tokitoh Organometallics, 2010, 29 (21), pp 4781–4784 {{doi. 10.1021/om100382n

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tin-heterocyclessix-membered-ringshypothetical-chemical-compoundstin(iv)-compounds