Lithium naphthalene

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Lithium naphthalene
A solution of lithium naphthalenide in tetrahydrofuran
Names
Preferred IUPAC name
Lithium naphthalenide
Identifiers
3D model (
JSmol
)
ChemSpider
  • InChI=1S/C10H8.Li/c1-2-6-10-8-4-3-7-9(10)5-1;/h1-8H;
    Key: PDZGAEAUKGKKDE-UHFFFAOYSA-N
SMILES
  • [Li].C1=CC=C2C=CC=CC2=C1
Properties
Li+[C10H8]−
Molar mass 135.11 g·mol−1
Appearance Dark green crystals
Related compounds
Other cations
 sodium naphthalene
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).

Lithium naphthalene is an organic

organic radical
.

Preparation and properties

The compound is prepared by stirring the metallic lithium with naphthalene in an ethereal solvent, usually as tetrahydrofuran or dimethoxyethane. The resulting salt is dark green.[2] The reaction of naphthalene with lithium can be accelerated by sonication. Methods for assaying lithium naphthalene have been developed as well.[3] As a radical, its solutions show a strong EPR signal near g = 2.0.[4] Its deep green color arises from absorptions at 463, 735 nm.[5]

Several

pm and the other nine C–C bonds elongate by 2–3 pm. Net: reduction weakens the bonding.[6]

Reactions

Redox

With a

normal hydrogen electrode, the naphthalene radical anion is a strong reducing agent.[5]

Protonation

The

alcohols. These reactions afford dihydronaphthalene
:

2 Li+[C10H8]− + 2 H2O → C10H10 + C10H8 + 2 LiOH

As a ligand precursor

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

Many related

tmeda)2]2[C10H8]2−.[8][1]

References

  1. ^
    PMID 19462646
    .
  2. doi:10.15227/orgsyn.084.0156
    .
  3. doi:10.15227/orgsyn.085.0053
    .
  4. ISBN 0-471-84997-9
  5. ^
    PMID 11848774
    .
  6. doi:10.1039/C5NJ02841H
    .
  7. S2CID 73436073
    .
  8. doi:10.1021/ja00776a014
    .
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