Stannabenzene

Stannabenzene
Names
	IUPAC name Stannine
	Other names Stannin
Identifiers
CAS Number	289-78-1 ;
3D model (JSmol)	Interactive image;
ChemSpider	20137777 ;
PubChem CID	119197;
CompTox Dashboard (EPA)	DTXSID70894913 ;
	InChI InChI=1S/C5H5.Sn.H/c1-3-5-4-2;;/h1-5H;;/b3-1?,5-4-;; Key: USOBSXNBGFXQQW-RJPIHQCFSA-N ;
	SMILES [H][Sn]1=CC=CC=C1;
Properties
Chemical formula	C5H6Sn
Molar mass	184.813 g·mol−1
	Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).

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,^[1] 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.^[2] 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.

A stable 2-stannanaphthalene derivative

Tbt-substituted 9-stannaphenanthrene was reported in 2005.^[3] At room temperature it forms the [4+2] cycloadduct.

Tbt-substituted stannabenzene was reported in 2010.^[4] At room-temperature it quantitatively forms the DA dimer.

Tbt-substituted stannabenzene synthesis. Reagents lithium aluminum hydride (step 2), NBS (step 3), LDA (step 4)

References

^ Ebrahimi, Arash Afshar; Ghiasi, Reza; Foroutan-Nejad, Cina (2010). "Topological characteristics of the ring critical points and the aromaticity of groups IIIA to VIA hetero-benzenes". Journal of Molecular Structure: THEOCHEM. 941 (1–3): 47–52. doi:10.1016/j.theochem.2009.10.038.
^ Mizuhata, Yoshiyuki; Sasamori, Takahiro; Takeda, Nobuhiro; Tokitoh, Norihiro (2006). "A Stable Neutral Stannaaromatic Compound: Synthesis, Structure and Complexation of a Kinetically Stabilized 2-Stannanaphthalene". Journal of the American Chemical Society. 128 (4): 1050–1. doi:10.1021/ja057531d. PMID 16433501.
^ 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
^ Generation of Stannabenzenes and Their Properties Yoshiyuki Mizuhata, Naoya Noda, and Norihiro Tokitoh Organometallics, 2010, 29 (21), pp 4781–4784 doi: 10.1021/om100382n

[1] Ebrahimi, Arash Afshar; Ghiasi, Reza; Foroutan-Nejad, Cina (2010). "Topological characteristics of the ring critical points and the aromaticity of groups IIIA to VIA hetero-benzenes". Journal of Molecular Structure: THEOCHEM. 941 (1–3): 47–52. doi:10.1016/j.theochem.2009.10.038.

[2] Mizuhata, Yoshiyuki; Sasamori, Takahiro; Takeda, Nobuhiro; Tokitoh, Norihiro (2006). "A Stable Neutral Stannaaromatic Compound: Synthesis, Structure and Complexation of a Kinetically Stabilized 2-Stannanaphthalene". Journal of the American Chemical Society. 128 (4): 1050–1. doi:10.1021/ja057531d. PMID 16433501.

[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

[1]

[2]

[3]

[4]

Stannabenzene

Stable derivatives of stannabenzene

See also

References