| 词条 | Stannabenzene |
| 释义 |
| Verifiedfields = changed | verifiedrevid = 470470486 | ImageFileL1 = Stannabenzene.svg | ImageSizeL1 = 80px | ImageAltL1 = | ImageFileR1 = Stannabenzene-Spartan-MP2-3D-balls.png | ImageSizeR1 = 120px | ImageFile2 = Stannabenzene-Spartan-MP2-3D-SF.png | ImageSize2 = 120px | IUPACName = Stannine | PIN = | OtherNames = Stannin |Section1={{Chembox Identifiers | ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}} | ChemSpiderID = 20137777 | StdInChI_Ref = {{stdinchicite|correct|chemspider}} | StdInChI = 1S/C5H5.Sn.H/c1-3-5-4-2;;/h1-5H;;/b3-1?,5-4-;; | StdInChIKey_Ref = {{stdinchicite|correct|chemspider}} | StdInChIKey = USOBSXNBGFXQQW-RJPIHQCFSA-N | CASNo_Ref = {{cascite|changed|??}} | CASNo = 289-78-1 | PubChem = | SMILES = [H][Sn]1=CC=CC=C1 }} |Section2={{Chembox Properties | C=5 | H=6 | Sn=1 | Appearance = | Density = | MeltingPt = | BoilingPt = | Solubility = }} |Section3={{Chembox Hazards | MainHazards = | FlashPt = | AutoignitionPt = }} }} 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,[1] but has not been isolated. Stable derivatives of stannabenzeneStable derivatives of stannabenzene have been isolated. The 2-stannanaphthalene depicted below is stable in an inert atmosphere at temperatures below 140 °C.[2] 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-tris[bis(trimethylsilyl)methyl]phenyl 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. {{clear left}} Tbt-substituted 9-stannaphenanthrene was reported in 2005.[3] At room temperature it forms the [4+2] cycloadduct. Tbt-substituted stannabenzene was reported in 2010.[4] At room-temperature it quantitatively forms the DA dimer. {{clear left}} See also
References1. ^{{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}} 2. ^{{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}} 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}} 2 : Tin heterocycles|Six-membered rings |
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