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{{Chembox {{Chembox
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| ImageFileL1 = Stannabenzene.svg |ImageFileL1 = Stannabenzene.svg
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| ImageFileR1 = Stannabenzene-Spartan-MP2-3D-balls.png |ImageFileR1 = Stannabenzene-Spartan-MP2-3D-balls.png
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| IUPACName = Stannine |PIN = Stannine
⚫ |OtherNames = Stannin
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⚫ |StdInChI = 1S/C5H5.Sn.H/c1-3-5-4-2;;/h1-5H;;/b3-1?,5-4-;;
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⚫ | C=5 | H=6 | Sn=1
⚫ | Section2 = {{Chembox Properties
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⚫ | C=5 | H=6 | Sn=1
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'''Stannabenzene''' (C<sub>5</sub>H<sub>6</sub>Sn) is the parent representative of a group of ]s that are related to ] with a ] atom replaced by a ] atom. Stannabenzene itself has been studied by ],<ref>{{cite journal | doi = 10.1016/j.theochem.2009.10.038 | author = Ebrahimi, Arash Afshar; Ghiasi, Reza; Foroutan-Nejad, Cina | title = Topological characteristics of the ring critical points and the aromaticity of groups IIIA to VIA hetero-benzenes | journal = Journal of Molecular Structure: THEOCHEM | year = 2010 | volume = 941 | issue = 1–3 | pages = 47–52}}</ref> but has not been isolated. '''Stannabenzene''' (C<sub>5</sub>H<sub>6</sub>Sn) is the parent representative of a group of ]s that are related to ] with a ] atom replaced by a ] atom. Stannabenzene itself has been studied by ],<ref>{{cite journal | doi = 10.1016/j.theochem.2009.10.038 |author1=Ebrahimi, Arash Afshar |author2=Ghiasi, Reza |author3=Foroutan-Nejad, Cina | title = Topological characteristics of the ring critical points and the aromaticity of groups IIIA to VIA hetero-benzenes | journal = Journal of Molecular Structure: THEOCHEM | year = 2010 | volume = 941 | issue = 1–3 | pages = 47–52}}</ref> but has not been isolated.


==Stable derivatives of stannabenzene== ==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.<ref>{{cite journal | last1 = Mizuhata | first1 = Yoshiyuki | last2 = Sasamori | first2 = Takahiro | last3 = Takeda | first3 = Nobuhiro | last4 = Tokitoh | first4 = Norihiro | title = A Stable Neutral Stannaaromatic Compound:  Synthesis, Structure and Complexation of a Kinetically Stabilized 2-Stannanaphthalene | journal = Journal of the American Chemical Society | volume = 128 | pages = 1050–1 | year = 2006 | doi = 10.1021/ja057531d | issue = 4 | pmid = 16433501}}</ref> The tin to carbon bond in this compound is shielded from potential reactants by two very bulky groups, one ] group and the even larger 2,4,6-trisphenyl or Tbt group. The two Sn-C bonds have ]s of 202.9 and 208.1 ] which are shorter than those for Sn-C single bonds (214 pm) and comparable to that of known Sn=C ]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 ]. Stable derivatives of stannabenzene have been isolated. The 2-stannanaphthalene depicted below is stable in an inert atmosphere at temperatures below 140&nbsp;°C.<ref>{{cite journal | last1 = Mizuhata | first1 = Yoshiyuki | last2 = Sasamori | first2 = Takahiro | last3 = Takeda | first3 = Nobuhiro | last4 = Tokitoh | first4 = Norihiro | title = A Stable Neutral Stannaaromatic Compound: Synthesis, Structure and Complexation of a Kinetically Stabilized 2-Stannanaphthalene | journal = Journal of the American Chemical Society | volume = 128 | pages = 1050–1 | year = 2006 | doi = 10.1021/ja057531d | issue = 4 | pmid = 16433501}}</ref> The tin to carbon bond in this compound is shielded from potential reactants by two very bulky groups, one ] group and the even larger 2,4,6-trisphenyl or Tbt group. The two Sn-C bonds have ]s of 202.9 and 208.1 ] which are shorter than those for Sn-C single bonds (214 pm) and comparable to that of known Sn=C ]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 ].


:]{{clear-left}} :]{{clear left}}


Tbt-substituted 9-stannaphenanthrene was reported in 2005 <ref>''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}}</ref>. At room temperature it forms the ]. Tbt-substituted 9-stannaphenanthrene was reported in 2005.<ref>''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}}</ref> At room temperature it forms the ].


Tbt-substituted stannabenzene was reported in 2010.<ref>''Generation of Stannabenzenes and Their Properties'' Yoshiyuki Mizuhata, Naoya Noda, and Norihiro Tokitoh Organometallics, 2010, 29 (21), pp 4781–4784 {{DOI| 10.1021/om100382n}}</ref>. At room-temperature it quantitatively forms the ]. Tbt-substituted stannabenzene was reported in 2010.<ref>''Generation of Stannabenzenes and Their Properties'' Yoshiyuki Mizuhata, Naoya Noda, and Norihiro Tokitoh Organometallics, 2010, 29 (21), pp 4781–4784 {{doi| 10.1021/om100382n}}</ref> At room-temperature it quantitatively forms the ].


:] (step 2), ] (step 3), ] (step 4) ]]{{clear-left}} :] (step 2), ] (step 3), ] (step 4) ]]{{clear left}}


==See also== ==See also==
* Other 6-membered aromatic rings with one carbon replaced by another group: ], ], ], ], ], ], ] * 6-membered aromatic rings with one carbon replaced by another group: ], ], ], stannabenzene, ], ], ], ], ], ], ], ]


==References== ==References==
{{reflist}} {{reflist}}


] ]
]

]
]
]
]

Latest revision as of 12:54, 14 April 2023

Stannabenzene
Names
Preferred IUPAC name Stannine
Other names Stannin
Identifiers
CAS Number
3D model (JSmol)
ChemSpider
PubChem CID
CompTox Dashboard (EPA)
InChI
  • InChI=1S/C5H5.Sn.H/c1-3-5-4-2;;/h1-5H;;/b3-1?,5-4-;;Key: USOBSXNBGFXQQW-RJPIHQCFSA-N
SMILES
  • 1=CC=CC=C1
Properties
Chemical formula C5H6Sn
Molar mass 184.813 g·mol
Except where otherwise noted, data are given for materials in their standard state (at 25 °C , 100 kPa). ☒N verify (what is  ?) Infobox references
Chemical compound

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, 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 group and the even larger 2,4,6-trisphenyl 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. At room temperature it forms the cycloadduct.

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

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

See also

References

  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
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