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.
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Names | |||
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Preferred IUPAC name
Stannine | |||
Other names
Stannin
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Identifiers | |||
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3D model (JSmol)
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PubChem CID
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CompTox Dashboard (EPA)
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Properties | |||
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).
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Infobox references
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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.
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.