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Latest revision as of 12:54, 14 April 2023 edit undoDePiep (talk | contribs)Extended confirmed users294,285 editsm →Stable derivatives of stannabenzene: WP:ALUM & {chembox/drugbox}: sp, replaced: lithium aluminum hydride → lithium aluminium hydrideTag: AWB |
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{{Chembox |
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| verifiedrevid = 414056092 |
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|verifiedrevid = 470470486 |
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| ImageFileL1 = Stannabenzene.svg |
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|ImageFileL1 = Stannabenzene.svg |
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| ImageSizeL1 = 80px |
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|ImageSizeL1 = 80px |
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|ImageFileR1 = Stannabenzene-Spartan-MP2-3D-balls.png |
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|ImageSizeR1 = 120px |
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| ImageFileR1 = Stannabenzene-Spartan-MP2-3D-balls.png |
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|ImageFile2 = Stannabenzene-Spartan-MP2-3D-SF.png |
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|ImageSize2 = 120px |
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| ImageFile2 = Stannabenzene-Spartan-MP2-3D-SF.png |
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|PIN = Stannine |
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|OtherNames = Stannin |
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| IUPACName = Stannine |
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|Section1={{Chembox Identifiers |
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| PIN = |
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|ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}} |
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| OtherNames = Stannin |
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|ChemSpiderID = 20137777 |
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| Section1 = {{Chembox Identifiers |
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| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}} |
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|StdInChI_Ref = {{stdinchicite|correct|chemspider}} |
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|StdInChI = 1S/C5H5.Sn.H/c1-3-5-4-2;;/h1-5H;;/b3-1?,5-4-;; |
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| ChemSpiderID = 20137777 |
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| StdInChI_Ref = {{stdinchicite|correct|chemspider}} |
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|StdInChIKey_Ref = {{stdinchicite|correct|chemspider}} |
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|StdInChIKey = USOBSXNBGFXQQW-RJPIHQCFSA-N |
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| StdInChI = 1S/C5H5.Sn.H/c1-3-5-4-2;;/h1-5H;;/b3-1?,5-4-;; |
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|CASNo_Ref = {{cascite|changed|??}} |
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| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}} |
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|CASNo = 289-78-1 |
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| StdInChIKey = USOBSXNBGFXQQW-RJPIHQCFSA-N |
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|PubChem = 119197 |
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| SMILES1 = c1cccc1 |
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|SMILES = 1=CC=CC=C1 |
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| CASNo = 289-78-1 |
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| PubChem = |
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|Section2={{Chembox Properties |
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| SMILES = 1=CC=CC=C1}} |
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| C=5 | H=6 | Sn=1 |
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| 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. |
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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 |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. |
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==Stable derivatives of stannabenzene== |
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==Stable derivatives of stannabenzene== |
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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 | year = 2006 | doi = 10.1021/ja057531d}}</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 ]. |
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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.<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 ]. |
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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 ]. |
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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 ]. |
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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 ]. |
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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 ]. |
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==See also== |
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==See also== |
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* Other 6-membered aromatic rings with one carbon replaced by another group: ], ], ], ], ], ], ] |
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* 6-membered aromatic rings with one carbon replaced by another group: ], ], ], stannabenzene, ], ], ], ], ], ], ], ] |
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==References== |
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