Lithium naphthalenide
Lithium naphthalene is an organic salt with the chemical formula. In the research laboratory, it is used as a reductant in the synthesis of organic, organometallic, and inorganic chemistry. It is usually generated in situ. Lithium naphthalene crystallizes with ligands bound to. The anion is a well-known example of an 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. The reaction of naphthalene with lithium can be accelerated by sonication. Methods for assaying lithium naphthalene have been developed as well. As a radical, its solutions show a strong EPR signal near g = 2.0. Its deep green color arises from absorptions at 463, 735 nm.Several solvates of lithium naphthalene have been characterized by X-ray crystallography. The effects are subtle, the outer pair of HC–CH bonds contract by 3 pm and the other nine C–C bonds elongate by 2–3 pm. Net: reduction weakens the bonding.