Sodium naphthalenide

Names
Preferred IUPAC name

Sodium naphthalenide

Systematic IUPAC name

Sodium naphthalen-1-ide

Other names

sodium naphthalenide, sodium naphthalide

Identifiers

CAS Number

* 3481-12-7

3D model (JSmol)

* Interactive image

ChemSpider |

* 10004279 N

EC Number |

* 222-460-3

PubChem CID

* 11829632

InChI

* InChI=1S/C10H8.Na/c1-2-6-10-8-4-3-7-9(10)5-1;/h1-8H;/q-1;+1 N

Key: NCVIXNVCXNGGBW-UHFFFAOYSA-N N

* InChI=1/C10H8.Na/c1-2-6-10-8-4-3-7-9(10)5-1;/h1-8H;/q-1;+1

Key: NCVIXNVCXNGGBW-UHFFFAOYAJ

SMILES

* c1ccc2=C[CH][CH-]C=c2c1.[Na+]

Properties

Chemical formula

| Na+

10H
8]−

Molar mass | 151.164 g·mol−1
Appearance  | Deep green crystals
Related compounds

Other anions

| Lithium naphthalene

Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).

N verify (what is YN ?)
Infobox references

Sodium naphthalenide is an organic salt with the chemical formula Na+
[[[Chemistry:Carbon|C]]
10H
8]−
. 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 ligands bound to Na+
.[1]

## Contents

* 1 Preparation and properties
* 2 Reactions
* 2.1 Redox
* 2.2 Protonation
* 2.3 As a ligand
* 3 Related reagents
* 4 References

## Preparation and properties

A solution of lithium naphthalenide, the lithium salt of naphthalene, in tetrahydrofuran.

The alkali metal naphthalene salts 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. Its deep green color arises from absorptions centered at 463 and 735 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 pm and the other nine C−C bonds elongate by 2–3 pm. The net effect is that reduction weakens the bonding.[5][6]

## Reactions

### Redox

With a reduction potential near −2.5 V vs NHE, the naphthalene radical anion is a strong reducing agent.[1] It is capable of defluorinating PTFE and is commonly used for chemically etching PTFE to allow adhesion.[7]

### Protonation

The anion is strongly basic, and a typical degradation pathway involves reaction with water and related protic sources such as alcohols. These reactions afford dihydronaphthalene:

2 Na+

10H
8]−
\+ 2 H
2O → C
10H
10 \+ C
10H
8 \+ 2 NaOH

### As a ligand

Alkali metal salts of the naphthalene radical anion are used to prepare complexes of naphthalene.[8]

## Related reagents

## References

1. ↑ 1.0 1.1 Connelly, Neil G.; Geiger, William E. (1996). "Chemical Redox Agents for Organometallic Chemistry". Chemical Reviews 96 (2): 877–910. doi:10.1021/cr940053x. PMID 11848774.
2. ↑ Corey, E. J.; Gross, Andrew W. (1987). "tert-Butyl-tert-octylamine". Org. Syntheses 65: 166. doi:10.15227/orgsyn.065.0166.
3. ↑ Cotton, F. Albert; Wilkinson, Geoffrey (1988), Advanced Inorganic Chemistry (5th ed.), New York: Wiley-Interscience, p. 139, ISBN 0-471-84997-9
4. ↑ Greenwood, Norman N.; Earnshaw, Alan (1984). Chemistry of the Elements. Oxford: Pergamon Press. p. 111. ISBN 978-0-08-022057-4. https://books.google.com/books?id=OezvAAAAMAAJ&q=0-08-022057-6&dq=0-08-022057-6&source=bl&ots=m4tIRxdwSk&sig=XQTTjw5EN9n5z62JB3d0vaUEn0Y&hl=en&sa=X&ei=UoAWUN7-EM6ziQfyxIDoCQ&ved=0CD8Q6AEwBA.
5. ↑ Bock, Hans; Arad, Claudia; Näther, Christian; Havlas, Zdenek (1995). "The Structures of Solvent-Separated Naphthalene and Anthracene Radical Anions". J. Chem. Soc., Chem. Commun. (23): 2393–2394. doi:10.1039/C39950002393.
6. ↑ Castillo, Maximiliano; Metta-Magaña, Alejandro J.; Fortier, Skye (2016). "Isolation of Gravimetrically Quantifiable Alkali Metal Arenides Using 18-Crown-6". New Journal of Chemistry 40 (3): 1923–1926. doi:10.1039/C5NJ02841H.
7. ↑ López, Cristian Daniel; Cedeño-Mata, Michelle; Dominguez-Pumar, Manuel; Bermejo, Sandra (December 2020). "Surface modification of polytetrafluoroethylene thin films by non-coherent UV light and water treatment for electrowetting applications". Progress in Organic Coatings 149. doi:10.1016/j.porgcoat.2020.105593.
8. ↑ Ellis, John E. (2019). "The Chatt Reaction: Conventional Routes to homoleptic Arenemetalates of d-Block Elements". Dalton Transactions 48 (26): 9538–9563. doi:10.1039/C8DT05029E. PMID 30724934.

* v
* t
* e

Sodium compounds

* NaAlO2
* NaBH4
* NaBH3(CN)
* NaBO2
* NaBiO3
* NaBr
* NaBrO
* NaBrO3
* NaCH3COO
* NaC6H5CO2
* NaC6H4(OH)CO2
* NaCN
* NaCl
* NaClO
* NaClO2
* NaClO3
* NaClO4
* NaF
* Na2FeO4
* NaH
* NaHCO3
* NaH2PO4
* NaHSO3
* NaHSO4
* NaI
* NaIO3
* NaIO4
* Na5IO6
* NaMnO4
* NaN3
* NaNH2
* NaNO2
* NaNO3
* NaOCN
* NaO2
* NaO3
* NaOH
* NaPO2H2
* NaReO4
* NaSCN
* NaSH
* NaTcO4
* NaVO3
* Na2CO3
* Na2C2O4
* Na2CrO4
* Na2Cr2O7
* Na2GeO3
* Na2MnO4
* Na3MnO4
* Na2MoO4
* Na2MoS4
* Na2N2O2
* Na2O
* Na2O2
* Na2O(UO3)2
* Na2PO3F
* Na2S
* Na2SO3
* Na2SO4
* Na2S2O3
* Na2S2O4
* Na2S2O5
* Na2S2O6
* Na2S2O7
* Na2S2O8
* Na2S4O6
* Na2Se
* Na2SeO3
* Na2SeO4
* Na2SiO3
* Na2Si2O5
* Na4SiO4
* Na2Te
* Na2TeO3
* Na2TeO4
* Na2Po
* Na2Ti3O7
* Na2U2O7
* Na2WO4
* Na2Zn(OH)4
* Na3N
* Na3P
* Na3PO4
* Na3VO4
* Na4Fe(CN)6
* Na4P3O7
* Na5P3O10

Chemical formulas

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