Sodium naphthalene

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Sodium naphthalenide
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Sodium naphthalene
Names
Preferred IUPAC name
Sodium naphthalenide
Systematic IUPAC name
Sodium naphthalen-1-ide
Other names
sodium naphthalenide, sodium naphthalide
Identifiers
3D model (
JSmol
)
ChemSpider
ECHA InfoCard
 100.020.420 Edit this at Wikidata
EC Number
  • 222-460-3
  • 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
  • c1ccc2=C[CH][CH-]C=c2c1.[Na+]
Properties
Na+[C10H8]−
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).
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Sodium naphthalene is an organic

solvate with ligands bound to Na+.[1]

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

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

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

NHE, the naphthalene radical anion is a strong reducing agent.[1]

Protonation

The anion is strongly

alcohols. These reactions afford dihydronaphthalene
:

2 Na+[C10H8]− + 2 H2O → C10H10 + C10H8 + 2 NaOH

As a ligand

Alkali metal salts of the naphthalene radical anion are used to prepare complexes of naphthalene.[7]

Related reagents

Main article: radical anion

References

  1. ^
    PMID 11848774
    .
  2. doi:10.15227/orgsyn.065.0166
    .
  3. ISBN 0-471-84997-9
  4. ISBN 978-0-08-022057-4
    .
  5. doi:10.1039/C39950002393
    .
  6. doi:10.1039/C5NJ02841H
    .
  7. S2CID 73436073
    .
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