Stannabenzene (C
5H
6Sn) is the parent representative of a group of
organotin compound
Organotin compounds or stannanes are chemical compounds based on tin with hydrocarbon substituents. Organotin chemistry is part of the wider field of organometallic chemistry. The first organotin compound was diethyltin diiodide (), discovered by ...
s 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
In chemistry, the valence (US spelling) or valency (British spelling) of an element is the measure of its combining capacity with o ...
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
Computational chemistry is a branch of chemistry that uses computer simulation to assist in solving chemical problems. It uses methods of theoretical chemistry, incorporated into computer programs, to calculate the structures and properties of m ...
, 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 betw ...
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.
:
See also
* 6-membered aromatic rings with one carbon replaced by another group:
borabenzene
Borabenzene is a hypothetical organoboron compound with the formula C5H5B. Unlike the related but highly stable benzene molecule, borabenzene would be electron-deficient. Related derivatives are the boratabenzene anions, including the parent 5H5 ...
,
silabenzene
A silabenzene is a heteroaromatic compound containing one or more silicon atoms instead of carbon atoms in benzene. A single substitution gives silabenzene proper; additional substitutions give a disilabenzene (3 theoretical isomers), trisilabenz ...
,
germabenzene
Germabenzene (C5H6Ge) is the parent representative of a group of chemical compounds containing in their molecular structure a benzene ring with a carbon atom replaced by a germanium atom. Germabenzene itself has been studied theoretically, and syn ...
, stannabenzene,
pyridine
Pyridine is a basic heterocyclic organic compound with the chemical formula . It is structurally related to benzene, with one methine group replaced by a nitrogen atom. It is a highly flammable, weakly alkaline, water-miscible liquid with a d ...
,
phosphorine
Phosphorine (IUPAC name: phosphinine) 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. It is a colorless liquid that is m ...
,
arsabenzene
Arsabenzene (IUPAC name: arsinine) is an organoarsenic heterocyclic compound with the chemical formula C5H5As. It belongs to a group of compounds called heteroarenes that have the general formula C5H5E (E= N, P, As, Sb, Bi).
This air sensitive li ...
,
bismabenzene
Bismabenzene () is the parent representative of a group of organobismuth compounds that are related to benzene with a carbon atom replaced by a bismuth atom. Bismabenzene itself has been synthesised but not isolated because it is too reactive, te ...
,
pyrylium
Pyrylium is a cation (positive ion) with formula , consisting of a six-membered ring of five carbon atoms, each with one hydrogen atom, and one positively charged oxygen atom. The bonds in the ring are conjugated as in benzene, giving it an aroma ...
,
thiopyrylium
Thiopyrylium is a cation with the chemical formula C5H5S+. It is analogous to the pyrylium cation with the oxygen atom replaced by a sulfur atom.
Thiopyrylium salts are less reactive than the analogous pyrylium salts due to the higher polarizabi ...
,
selenopyrylium
Selenopyrylium is an aromatic heterocyclic compound consisting of a six-membered ring with five carbon atoms and a positively charged selenium atom.
Naming and numbering
Formerly it was named selenapyrylium. However, this is misleading as "selena ...
,
telluropyrylium
Telluropyrylium is an aromatic heterocyclic compound consisting of a six member ring with five carbon atoms, and a positively charged tellurium atom. Derivatives of telluropyrylium are important in research of infrared dyes.
Naming and numbering ...
References
{{reflist
Tin heterocycles
Six-membered rings
Hypothetical chemical compounds
Tin(IV) compounds