Stannabenzene (C₅H₆Sn) is the parent representative of a group of organotin compounds that are related to

benzene Benzene is an organic chemical compound with the molecular formula C6H6. The benzene molecule is composed of six carbon atoms joined in a planar ring with one hydrogen atom attached to each. Because it contains only carbon and hydrogen atoms ...

with a

carbon Carbon () is a chemical element with the symbol C and atomic number 6. It is nonmetallic and tetravalent—its atom making four electrons available to form covalent chemical bonds. It belongs to group 14 of the periodic table. Carbon mak ...

atom replaced by a

tin Tin is a chemical element with the symbol Sn (from la, stannum) and atomic number 50. Tin is a silvery-coloured metal. Tin is soft enough to be cut with little force and a bar of tin can be bent by hand with little effort. When bent, t ...

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 In organic chemistry, butyl is a four-carbon alkyl radical or substituent group with general chemical formula , derived from either of the two isomers (''n''-butane and isobutane) of butane. The isomer ''n''-butane can connect in two ways, givi ...

group and the even larger 2,4,6-tris

is(trimethylsilyl)methyl In linguistics, a copula (plural: copulas or copulae; abbreviated ) is a word or phrase that links the subject of a sentence to a subject complement, such as the word ''is'' in the sentence "The sky is blue" or the phrase ''was not being'' i ...

henyl or Tbt group. The two Sn-C bonds have

bond length In molecular geometry, bond length or bond distance is defined as the average distance between nuclei of two bonded atoms in a molecule. It is a transferable property of a bond between atoms of fixed types, relatively independent of the rest of ...

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 In chemistry, a double bond is a covalent bond between two atoms involving four bonding electrons as opposed to two in a single bond. Double bonds occur most commonly between two carbon atoms, for example in alkenes. Many double bonds exist betwee ...

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 In chemistry, aromaticity is a chemical property of cyclic ( ring-shaped), ''typically'' planar (flat) molecular structures with pi bonds in resonance (those containing delocalized electrons) that gives increased stability compared to satur ...

. :

Tbt-substituted 9-stannaphenanthrene was reported in 2005. At room temperature it forms the +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 At room-temperature it quantitatively forms the DA dimer. : Stannabenzene Mizuhata 2010

References

{{reflist Tin heterocycles Six-membered rings Hypothetical chemical compounds Tin(IV) compounds

Stable derivatives of stannabenzene

See also

References