| Revision as of 15:47, 6 December 2011 editBeetstra (talk | contribs)Edit filter managers, Administrators172,031 edits Saving copy of the {{chembox}} taken from revid 454232561 of page Sodium_naphthalenide for the Chem/Drugbox validation project (updated: ''). |
Latest revision as of 12:58, 10 December 2024 edit A Shortfall Of Gravitas (talk | contribs)Extended confirmed users700 edits →Reactions: Add cite for etching PTFE (covers etching fluoropolymers in general and by a newer UV method, this chemical is mentioned as the most common method). |
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{{ambox | text = This page contains a copy of the infobox ({{tl|chembox}}) taken from revid of page ] with values updated to verified values.}} |
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| verifiedrevid = 464402496 |
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| PIN = Sodium naphthalenide |
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| SystematicName = Sodium naphthalen-1-ide |
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| PIN = Sodium naphthalenide |
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| SystematicName = Sodium naphthalen-1-ide |
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| ImageFile = Sodium naphthalenide.svg |
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| OtherNames = sodium naphthalenide, sodium naphthalide |
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| ImageFile = Sodium naphthalenide.svg |
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| ImageSize = 200px |
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| Section1 = {{Chembox Identifiers |
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|Section1={{Chembox Identifiers |
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| CASNo=3481-12-7 |
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| InChIKey1 = QLUMLEDLZDMGDW-UHFFFAOYSA-N |
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| EINECS = 222-460-3 |
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| ChemSpiderID = 10617745 |
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| PubChem = 11829632 |
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| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}} |
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| ChemSpiderID_Ref = {{chemspidercite|changed|chemspider}} |
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| EINECS = 222-460-3 |
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| ChemSpiderID = 10004279 |
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| InChI = 1S/C10H7.Na/c1-2-6-10-8-4-3-7-9(10)5-1;/h1-7H;/q-1;+1 |
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| SMILES = .1cccc2ccccc12 |
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| SMILES = c1ccc2=CC=c2c1. |
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| InChI = 1/C10H8.Na/c1-2-6-10-8-4-3-7-9(10)5-1;/h1-8H;/q-1;+1 |
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| StdInChI_Ref = {{stdinchicite|correct|chemspider}} |
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| InChIKey = NCVIXNVCXNGGBW-UHFFFAOYAJ |
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| StdInChI = 1S/C10H7.Na/c1-2-6-10-8-4-3-7-9(10)5-1;/h1-7H;/q-1;+1 |
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| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}} |
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| StdInChI = 1S/C10H8.Na/c1-2-6-10-8-4-3-7-9(10)5-1;/h1-8H;/q-1;+1 |
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| StdInChIKey = QLUMLEDLZDMGDW-UHFFFAOYSA-N}} |
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| StdInChIKey_Ref = {{stdinchicite|changed|chemspider}} |
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| Section2 = {{Chembox Properties |
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| StdInChIKey = NCVIXNVCXNGGBW-UHFFFAOYSA-N}} |
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| Na = 1 | C = 10 | H = 8 |
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|Section2={{Chembox Properties |
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| Appearance = |
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| Formula = {{chem2|Na+−}} |
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| Density = |
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| Na=1 | C=10 | H=8 |
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| Appearance = Deep green crystals |
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'''Sodium naphthalene''' is an organic ] with the chemical formula {{chem2|Na+−|auto=1}}. In the research laboratory, it is used as a ] in the synthesis of organic, ], and inorganic chemistry. It is usually generated in situ. When isolated, it invariably crystallizes as a ] with ]s bound to {{chem2|Na+}}.<ref name=Connelly>{{cite journal|doi=10.1021/cr940053x|title=Chemical Redox Agents for Organometallic Chemistry|year=1996|last1=Connelly|first1=Neil G.|last2=Geiger|first2=William E.|journal=Chemical Reviews|volume=96|issue=2|pages=877–910|pmid=11848774}}</ref> |
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==Preparation and properties== |
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], the lithium salt of naphthalene, in ].]] |
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The alkali metal naphthalene salts are prepared by stirring the metal with ] in an ]eal solvent, usually as ] or ]. The resulting salt is dark green.<ref>{{cite journal|journal=Org. Syntheses | doi=10.15227/orgsyn.065.0166 | last1= Corey |first1=E. J. |last2=Gross |first2=Andrew W. | title = ''tert''-Butyl-''tert''-octylamine | volume=65 | pages = 166 | year = 1987}}</ref><ref>{{Cotton&Wilkinson5th|page=139}}</ref><ref>{{Greenwood&Earnshaw1st|page=111}}</ref> The ] is a ], giving a strong ] signal near ''g'' = 2.0. Its deep green color arises from absorptions centered at 463 and 735 nm. |
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Several solvates of sodium naphthalenide have been characterized by ]. The effects are subtle, the outer pair of CH−CH bonds contract by 3 ] and the other nine C−C bonds elongate by 2–3 pm. The net effect is that reduction weakens the bonding.<ref>{{cite journal |doi=10.1039/C39950002393|title=The Structures of Solvent-Separated Naphthalene and Anthracene Radical Anions|year=1995|last1=Bock|first1=Hans|last2=Arad|first2=Claudia|last3=Näther|first3=Christian|last4=Havlas|first4=Zdenek|journal=J. Chem. Soc., Chem. Commun.|issue=23|pages=2393–2394}}</ref><ref>{{cite journal |doi=10.1039/C5NJ02841H|title=Isolation of Gravimetrically Quantifiable Alkali Metal Arenides Using 18-Crown-6|year=2016|last1=Castillo|first1=Maximiliano|last2=Metta-Magaña|first2=Alejandro J.|last3=Fortier|first3=Skye|journal=New Journal of Chemistry|volume=40|issue=3|pages=1923–1926}}</ref> |
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==Reactions== |
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=== Redox === |
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With a ] near −2.5 V vs ], the naphthalene radical anion is a strong ].<ref name=Connelly/> It is capable of defluorinating ] and is commonly used for ] to allow adhesion.<ref>{{cite journal |last1=López |first1=Cristian Daniel |last2=Cedeño-Mata |first2=Michelle |last3=Dominguez-Pumar |first3=Manuel |last4=Bermejo |first4=Sandra |title=Surface modification of polytetrafluoroethylene thin films by non-coherent UV light and water treatment for electrowetting applications |journal=Progress in Organic Coatings |date=December 2020 |volume=149 |pages=105593 |doi=10.1016/j.porgcoat.2020.105593}}</ref> |
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=== Protonation === |
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The anion is strongly ], and a typical degradation pathway involves reaction with water and related ] sources such as ]. These reactions afford ]: |
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:{{chem2|2 Na+− + 2 H2O → ] + ] + 2 ]}} |
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=== As a ligand === |
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] salts of the naphthalene radical anion are used to prepare ] of ].<ref>{{cite journal |doi=10.1039/C8DT05029E|title=The Chatt Reaction: Conventional Routes to homoleptic Arenemetalates of d-Block Elements|year=2019|last1=Ellis|first1=John E.|journal=Dalton Transactions|volume=48|issue=26|pages=9538–9563|pmid=30724934|s2cid=73436073}}</ref> |
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==Related reagents== |
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{{main|radical anion}} |
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==References== |
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{{reflist}} |
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<!--these look specialized and obsolete, unless they describe the discovery of the anion {{cite journal | doi = 10.1021/ja01627a017 | title = Reducing Action of Sodium Naphthalide in Tetrahydrofuran Solution. I. The Reduction of Cobalt(II) Chloride | year = 1955 | author = Ting, Li Chu; Joseph V. Friel | journal = ]| volume = 77 | pages = 5838–5840 | issue = 22}}</ref><ref>{{cite journal | doi = 10.1021/ja01642a004 | title = The Magnetic Susceptibilities of Some Aromatic Hydrocarbon Anions | year = 1954 |author1=Ting, Li Chu |author2=Yu, Shan Chi | journal = ]| volume = 76 | pages = 3367–3369 | issue = 13}}--> |
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{{sodium compounds}} |
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