Stannabenzene is the parent representative of a group of organotin compounds that are related to benzene

Benzene

Benzene is an organic chemical compound. It is composed of 6 carbon atoms in a ring, with 1 hydrogen atom attached to each carbon atom, with the molecular formula C6H6....

 with a carbon

Carbon

Carbon is the chemical element with symbol C and atomic number 6. As a member of group 14 on the periodic table, it is nonmetallic and tetravalent—making four electrons available to form covalent chemical bonds...

 atom replaced by a tin

Tin

Tin is a chemical element with the symbol Sn and atomic number 50. It is a main group metal in group 14 of the periodic table. Tin shows chemical similarity to both neighboring group 14 elements, germanium and lead and has two possible oxidation states, +2 and the slightly more stable +4...

 atom. Stannabenzene itself has been studied by computational chemistry

Computational chemistry

Computational chemistry is a branch of chemistry that uses principles of computer science to assist in solving chemical problems. It uses the results of theoretical chemistry, incorporated into efficient computer programs, to calculate the structures and properties of molecules and solids...

, but has not been isolated.

Stable derivatives of stannabenzene

Stable derivatives of stannabenzene are 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 length

Bond length

- Explanation :Bond length is related to bond order, when more electrons participate in bond formation the bond will get shorter. Bond length is also inversely related to bond strength and the bond dissociation energy, as a stronger bond will be shorter...

s 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 bond

Double bond

A double bond in chemistry is a chemical bond between two chemical elements involving four bonding electrons instead of the usual two. The most common double bond, that between two carbon atoms, can be found in alkenes. Many types of double bonds between two different elements exist, for example in...

s (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 . At room temperature it forms the [4+2] cycloadduct

Cycloaddition

A cycloaddition is a pericyclic chemical reaction, in which "two or more unsaturated molecules combine with the formation of a cyclic adduct in which there is a net reduction of the bond multiplicity." The resulting reaction is a cyclization reaction.Cycloadditions are usually described by the...

.

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

Diels-Alder reaction

The Diels–Alder reaction is an organic chemical reaction between a conjugated diene and a substituted alkene, commonly termed the dienophile, to form a substituted cyclohexene system. The reaction can proceed even if some of the atoms in the newly formed ring are not carbon...

.

See also

• Other 6-membered aromatic rings with one carbon replaced by another group: borabenzene
  Borabenzene
  A borabenzene is a heteroaromatic compound that has a boron atom instead of the carbon atom of a benzene molecule. A free borabenzene, which has no donor ligand on the boron atom, has not yet been isolated despite its simple structure and the chemical robustness of boron-carbon bonds...
  
  , benzene
  Benzene
  Benzene is an organic chemical compound. It is composed of 6 carbon atoms in a ring, with 1 hydrogen atom attached to each carbon atom, with the molecular formula C6H6....
  
  , silabenzene
  Silabenzene
  A silabenzene is a heteroaromatic compound containing one or more silicon atoms instead of carbon atom in benzene. A single substitution gives silabenzene proper; additional substitutions give a disilabenzene , trisilabenzene , etc.Silabenzenes have been the targets of many theoretical and...
  
  , germabenzene, pyridine
  Pyridine
  Pyridine is a basic heterocyclic organic compound with the chemical formula C5H5N. It is structurally related to benzene, with one C-H group replaced by a nitrogen atom...
  
  , phosphorine
  Phosphorine
  Phosphorine is a heavier element analog of pyridine, containing a phosphorus atom instead of an aza- moiety. It is also called phosphabenzene and belongs to the phosphaalkene class. Phosphorine is a planar aromatic compound with 88% of the aromaticity of that of benzene...
  
  , pyrylium salt
  Pyrylium salt
  A pyrylium salt is a salt containing a pyrylium cation or a derivative of it. The pyrylium cation is a conjugated 6-membered carbon ring system with one carbon atom replaced by a positively charged oxygen atom. It is, like benzene, an aromatic compound...