| Revision as of 17:54, 9 January 2012 editBeetstra (talk | contribs)Edit filter managers, Administrators172,031 edits Saving copy of the {{chembox}} taken from revid 467591890 of page Stannabenzene for the Chem/Drugbox validation project (updated: 'CASNo'). |
Latest revision as of 12:54, 14 April 2023 edit DePiep (talk | contribs)Extended confirmed users294,285 editsm →Stable derivatives of stannabenzene: WP:ALUM & {chembox/drugbox}: sp, replaced: lithium aluminum hydride → lithium aluminium hydrideTag: AWB |
| Line 1: |
Line 1: |
|
{{ambox | text = This page contains a copy of the infobox ({{tl|chembox}}) taken from revid of page ] with values updated to verified values.}} |
|
|
{{Chembox |
|
{{Chembox |
|
|
|Verifiedfields = changed |
|
| verifiedrevid = 427947810 |
|
|verifiedrevid = 470470486 |
|
| ImageFileL1 = Stannabenzene.svg |
|
|ImageFileL1 = Stannabenzene.svg |
|
| ImageSizeL1 = 80px |
|
|ImageSizeL1 = 80px |
|
| ImageAltL1 = |
|
|
| ImageFileR1 = Stannabenzene-Spartan-MP2-3D-balls.png |
|
|ImageFileR1 = Stannabenzene-Spartan-MP2-3D-balls.png |
|
| ImageSizeR1 = 120px |
|
|ImageSizeR1 = 120px |
|
| ImageFile2 = Stannabenzene-Spartan-MP2-3D-SF.png |
|
|ImageFile2 = Stannabenzene-Spartan-MP2-3D-SF.png |
|
| ImageSize2 = 120px |
|
|ImageSize2 = 120px |
|
| IUPACName = Stannine |
|
|PIN = Stannine |
|
⚫ |
|OtherNames = Stannin |
|
| PIN = |
|
|
⚫ |
|Section1={{Chembox Identifiers |
| ⚫ |
| OtherNames = Stannin |
|
|
⚫ |
|ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}} |
| ⚫ |
| Section1 = {{Chembox Identifiers |
|
|
⚫ |
|ChemSpiderID = 20137777 |
| ⚫ |
| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}} |
|
|
⚫ |
|StdInChI_Ref = {{stdinchicite|correct|chemspider}} |
| ⚫ |
| ChemSpiderID = 20137777 |
|
|
⚫ |
|StdInChI = 1S/C5H5.Sn.H/c1-3-5-4-2;;/h1-5H;;/b3-1?,5-4-;; |
| ⚫ |
| StdInChI_Ref = {{stdinchicite|correct|chemspider}} |
|
|
⚫ |
|StdInChIKey_Ref = {{stdinchicite|correct|chemspider}} |
| ⚫ |
| StdInChI = 1S/C5H5.Sn.H/c1-3-5-4-2;;/h1-5H;;/b3-1?,5-4-;; |
|
|
⚫ |
|StdInChIKey = USOBSXNBGFXQQW-RJPIHQCFSA-N |
| ⚫ |
| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}} |
|
|
⚫ |
|CASNo_Ref = {{cascite|changed|??}} |
| ⚫ |
| StdInChIKey = USOBSXNBGFXQQW-RJPIHQCFSA-N |
|
|
| SMILES1 = c1cccc1 |
|
|CASNo = 289-78-1 |
|
⚫ |
|PubChem = 119197 |
| ⚫ |
| CASNo_Ref = {{cascite|correct|??}} |
|
|
⚫ |
|SMILES = 1=CC=CC=C1 |
|
| CASNo = <!-- blanked - oldvalue: 289-78-1 --> |
|
| ⚫ |
| PubChem = |
|
| ⚫ |
| SMILES = 1=CC=CC=C1}} |
|
| ⚫ |
| Section2 = {{Chembox Properties |
|
| ⚫ |
| C=5 | H=6 | Sn=1 |
|
|
| Appearance = |
|
|
| Density = |
|
|
| MeltingPt = |
|
|
| BoilingPt = |
|
|
| Solubility = }} |
|
|
| Section3 = {{Chembox Hazards |
|
|
| MainHazards = |
|
|
| FlashPt = |
|
|
| Autoignition = }} |
|
|
}} |
|
}} |
|
⚫ |
|Section2={{Chembox Properties |
|
⚫ |
| C=5 | H=6 | Sn=1 |
|
|
}} |
|
|
}} |
|
|
|
|
|
'''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 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 ]. |
|
|
|
|
|
:]{{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 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}} |
|
|
|
|
|
==See also== |
|
|
* 6-membered aromatic rings with one carbon replaced by another group: ], ], ], stannabenzene, ], ], ], ], ], ], ], ] |
|
|
|
|
|
==References== |
|
|
{{reflist}} |
|
|
|
|
|
] |
|
|
] |
|
|
] |
|
|
] |