Sodium naphthalenide

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Sodium naphthalenide
Sodium naphthalenide.svg
Identifiers
PubChem 11829632
ChemSpider 10004279 N
EC number 222-460-3
Jmol-3D images Image 1
Properties
Molecular formula C10H8Na
Molar mass 151.16 g mol−1
Related compounds
Other anions Sodium cyclopentadienide
Except where noted otherwise, data are given for materials in their standard state (at 25 °C (77 °F), 100 kPa)
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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[edit]

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[edit]

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.


A solution of lithium naphthalenide, a related compound, in tetrahydrofuran


References[edit]

  1. ^ 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
  2. ^ Corey, E. J.; Gross, Andrew W. (1993), "tert-Butyl-tert-octylamine", Org. Synth. ; Coll. Vol. 8: 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 0-08-022057-6.