Sodium naphthalene

Sodium naphthalene
Names
	Preferred IUPAC name Sodium naphthalenide
	Systematic IUPAC name Sodium naphthalen-1-ide
Identifiers
3D model (JSmol)	Interactive image;
ChemSpider	10004279 ;
ECHA InfoCard	100.020.420
EC Number	222-460-3;
PubChem CID	11829632;
CompTox Dashboard (EPA)	DTXSID50188347 ;
	InChI InChI=1S/C10H8.Na/c1-2-6-10-8-4-3-7-9(10)5-1;/h1-8H;/q-1;+1 Key: NCVIXNVCXNGGBW-UHFFFAOYSA-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	C10H8Na
Molar mass	151.164 g·mol−1
Related compounds
Other anions	Sodium cyclopentadienide
	Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). verify (what is ?) Infobox references

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 properties

The 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 reagents

For some synthetic operations, sodium naphthalenide is excessively reducing (too negative), in which case milder reductants are selected. Larger rings give milder reductants. Sodium acenaphthenide is milder by about 0.75 V.

The corresponding lithium salt, lithium naphthalenide, is also known.

References

^ ^a ^b N. G. Connelly and W. E. Geiger, "Chemical Redox Agents for Organometallic Chemistry", Chem. Rev. 1996, 96, 877-910. doi:10.1021/cr940053x
^ Corey, E. J.; Gross, Andrew W. (1993). "tert-Butyl-tert-octylamine". Organic Syntheses{{cite journal}}: CS1 maint: multiple names: authors list (link); Collected Volumes, vol. 8, p. 93.
^ Cotton, F. Albert; Wilkinson, Geoffrey (1988), Advanced Inorganic Chemistry (5th ed.), New York: Wiley-Interscience, p. 139, ISBN 0-471-84997-9
^ Greenwood, Norman N.; Earnshaw, Alan (1984). Chemistry of the Elements. Oxford: Pergamon Press. p. 111. ISBN 978-0-08-022057-4.

[Connelly-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] Corey, E. J.; Gross, Andrew W. (1993). "tert-Butyl-tert-octylamine". Organic Syntheses{{cite journal}}: CS1 maint: multiple names: authors list (link); Collected Volumes, vol. 8, p. 93.

[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.

[1]

[2]

[3]

[4]