| 词条 | Sodium naphthalenide |
| 释义 |
| Verifiedfields = changed | Watchedfields = changed | verifiedrevid = 464402496 | PIN = Sodium naphthalenide | SystematicName = Sodium naphthalen-1-ide | ImageFile = Sodium naphthalenide.svg |Section1={{Chembox Identifiers | EINECS = 222-460-3 | PubChem = 11829632 | ChemSpiderID_Ref = {{chemspidercite|changed|chemspider}} | ChemSpiderID = 10004279 | SMILES = c1ccc2=C[CH][CH-]C=c2c1.[Na+] | InChI = 1/C10H8.Na/c1-2-6-10-8-4-3-7-9(10)5-1;/h1-8H;/q-1;+1 | InChIKey = NCVIXNVCXNGGBW-UHFFFAOYAJ | StdInChI_Ref = {{stdinchicite|changed|chemspider}} | StdInChI = 1S/C10H8.Na/c1-2-6-10-8-4-3-7-9(10)5-1;/h1-8H;/q-1;+1 | StdInChIKey_Ref = {{stdinchicite|changed|chemspider}} | StdInChIKey = NCVIXNVCXNGGBW-UHFFFAOYSA-N}} |Section2={{Chembox Properties | Na=1 | C=10 | H=8 | Appearance = | Density = | MeltingPt = | BoilingPt = | Solubility = }} |Section3={{Chembox Hazards | MainHazards = | FlashPt = | AutoignitionPt = }} |Section4={{Chembox Related | OtherAnions = Sodium cyclopentadienide }}Sodium naphthalenide, also known as sodium naphthalide, is an organic salt with the formula Na+C10H8−. In the research laboratory, it is used as a reductant in the synthesis of organic, organometallic, and inorganic chemistry. It has not been isolated as a solid, but it is usually prepared fresh before use.[1] Preparation and propertiesThe alkali metal naphthalenides are prepared by stirring the metal with naphthalene in an ethereal solvent, usually as tetrahydrofuran or dimethoxyethane. The resulting salt is dark green.[2][3][4] The anion is a radical, giving a strong EPR signal near g = 2.0, with a reduction potential near -2.5 V vs NHE. Its deep green color arises from absorptions centered at 463, 735 nm.[1] The anion is strongly basic, and a typical degradation pathway involves reaction with water and related protic sources. These reactions afford dihydronaphthalene: 2 NaC10H8 + 2 H2O → C10H10 + C10H8 + 2 NaOH Related reagentsFor some synthetic operations, sodium naphthalenide is excessively reducing (too negative) or too insoluble. In such cases, alternative reductants are selected.
References1. ^1 N. G. Connelly and W. E. Geiger, "Chemical Redox Agents for Organometallic Chemistry", Chem. Rev. 1996, 96, 877-910. {{DOI|10.1021/cr940053x}} 2. ^{{OrgSynth | prep=cv8p0093 | last= Corey |first=E. J. |last2=Gross |first2=Andrew W. |lastauthoramp=y | title = tert-Butyl-tert-octylamine | collvol = 8 | collvolpages = 93 | year = 1993}} 3. ^{{Cotton&Wilkinson5th|page=139}} 4. ^{{Greenwood&Earnshaw1st|page=111}} 5. ^{{cite journal|title=Highly Reactive Calcium for the Preparation of Organocalcium Reagents: 1-Adamantyl Calcium Halides and Their Addition to Ketones: 1-(1-Adamantyl)cyclohexanol|first=Reuben D. |last=Rieke |first2=Tse-Chong |last2=Wu |first3=Loretta I. |last3=Rieke |lastauthoramp=y |journal=Org. Synth.|year=1995|volume=72|page=147|doi=10.15227/orgsyn.072.0147}} 6. ^{{cite journal|last=Liu |first=X. |last2=Ellis |first2=J. E. |title=Hexacarbonylvanadate(1−) and Hexacarbonylvanadium(0) |journal=Inorg. Synth.|date=2004 |volume=34 |pages=96–103 |DOI=10.1002/0471653683.ch3| ISBN=0-471-64750-0}} 4 : Sodium compounds|One-electron reducing agents|Organosodium compounds|Free radicals |
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