Sodium naphthalenide

Sodium naphthalenide
Preferred IUPAC name

Sodium naphthalenide
Systematic name

Sodium naphthalen-1-ide
Identifiers
ChemSpider 10617745 Y
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
 Y (verify) (what is: Y/N?)
Except where noted otherwise, data are given for materials in their standard state (at 25 °C, 100 kPa)
Infobox references

Sodium naphthalenide, also known as sodium naphthalide, is a soluble one-electron reductant employed in organic, organometallic, and inorganic chemistry.[1][2] It is prepared by stirring sodium metal with naphthalene in a polar solvent such as tetrahydrofuran or dimethoxyethane, resulting in the formation of a dark green solution.[3][4][5] It cannot be stored as a solid, so it must be prepared fresh immediately before using it.

References

  1. ^ Ting, Li Chu; Joseph V. Friel (1955). "Reducing Action of Sodium Naphthalide in Tetrahydrofuran Solution. I. The Reduction of Cobalt(II) Chloride". J. Am. Chem. Soc. 77 (22): 5838–5840. doi:10.1021/ja01627a017. 
  2. ^ Ting, Li Chu; Yu, Shan Chi (1954). "The Magnetic Susceptibilities of Some Aromatic Hydrocarbon Anions". J. Am. Chem. Soc. 76 (13): 3367–3369. doi:10.1021/ja01642a004. 
  3. ^ Corey, E. J.; Gross, Andrew W. (1993), "tert-Butyl-tert-octylamine", Org. Synth., http://www.orgsyn.org/orgsyn/orgsyn/prepContent.asp?prep=cv8p0093 ; Coll. Vol. 8: 93 
  4. ^ Cotton, F. Albert; Wilkinson, Geoffrey (1988), Advanced Inorganic Chemistry (5th ed.), New York: Wiley-Interscience, p. 139, ISBN 0-471-84997-9 
  5. ^ Greenwood, Norman N.; Earnshaw, A. (1984). Chemistry of the Elements. Oxford: Pergamon. p. 111. ISBN 0-08-022057-6.