Wikipedia:WikiProject Chemicals/Chembox validation/VerifiedDataSandbox and Sodium naphthalene: Difference between pages

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SystematicName = Sodium naphthalen-1-ide

| = naphthalenide

| = Sodium naphthalenide

|Section1={{Chembox Identifiers

| CASNo=3481-12-7

| EINECS = 222-460-3

| PubChem = 11829632

| ChemSpiderID_Ref = {{chemspidercite||chemspider}}

| ChemSpiderID =

| SMILES = [][-]

| InChI = /.Na/c1-2-6-10-8-4-3-7-9(10)5-1;/h1-;/q-1;+1

| InChIKey = NCVIXNVCXNGGBW-UHFFFAOYAJ

| = {{stdinchicite||chemspider}}

| StdInChI = 1S/.Na/c1-2-6-10-8-4-3-7-9(10)5-1;/h1-;/q-1;+1

| = {{stdinchicite||chemspider}}

| StdInChIKey = -UHFFFAOYSA-N}}

|Section2={{Chembox Properties

| Formula = {{chem2|Na+[C10H8]−}}

| =

| Appearance =

|Section3={{Chembox

| OtherAnions = [[ ]]

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'''Sodium naphthalene''' is an organic [[salt (chemistry)|salt]] with the chemical formula {{chem2|Na+[C10H8]−|auto=1}}. In the research laboratory, it is used as a [[reductant]] in the synthesis of organic, [[organometallic]], and inorganic chemistry. It is usually generated in situ. When isolated, it invariably crystallizes as a [[solvate]] with [[ligand]]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>

==Preparation and properties==

[[File:Lithium Naphthalenide.jpg|thumb|left|upright|A solution of [[Lithium naphthalene|lithium naphthalenide]], the lithium salt of naphthalene, in [[tetrahydrofuran]].]]

The alkali metal naphthalene salts are prepared by stirring the metal with [[naphthalene]] in an [[ether]]eal solvent, usually as [[tetrahydrofuran]] or [[dimethoxyethane]]. 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 [[anion]] is a [[Radical (chemistry)|radical]], giving a strong [[Electron paramagnetic resonance|EPR]] signal near ''g''&nbsp;=&nbsp;2.0. Its deep green color arises from absorptions centered at 463 and 735&nbsp;nm.

Several solvates of sodium naphthalenide have been characterized by [[X-ray crystallography]]. The effects are subtle, the outer pair of CH−CH bonds contract by 3&nbsp;[[picometer|pm]] and the other nine C−C bonds elongate by 2–3&nbsp;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>

==Reactions==

=== Redox ===

With a [[reduction potential]] near −2.5&nbsp;V vs [[normal hydrogen electrode|NHE]], the naphthalene radical anion is a strong [[reducing agent]].<ref name=Connelly/> It is capable of defluorinating [[Polytetrafluoroethylene|PTFE]] and is commonly used for [[Surface treatment of PTFE|chemically etching PTFE]] 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>

=== Protonation ===

The anion is strongly [[Base (chemistry)|basic]], and a typical degradation pathway involves reaction with water and related [[protic]] sources such as [[alcohols]]. These reactions afford [[Dialin|dihydronaphthalene]]:

:{{chem2|2 Na+[C10H8]− + 2 H2O → [[Dialin|C10H10]] + [[naphthalene|C10H8]] + 2 [[Sodium hydroxide|NaOH]]}}

=== As a ligand ===

[[Alkali metal]] salts of the naphthalene radical anion are used to prepare [[Coordination complex|complexes]] of [[naphthalene]].<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>

==Related reagents==

{{main|radical anion}}

==References==

{{reflist}}

<!--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 = [[J. Am. Chem. Soc.]]| 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 = [[J. Am. Chem. Soc.]]| volume = 76 | pages = 3367–3369 | issue = 13}}-->

{{sodium compounds}}

[[Category:One-electron reducing agents]]

[[Category:Organosodium compounds]]

[[Category:Free radicals]]

[[Category:Naphthalenes]]