Naphthoxide

Naphthoxide refers to the anion formed when a naphthol deprotonates. Naphthols are aromatic organic compounds that contain a hydroxyl group (-OH) attached to a naphthalene ring system. Naphthalene is a bicyclic aromatic hydrocarbon. When a naphthol loses a proton (H+), it forms a naphthoxide anion, which carries a negative charge delocalized across the aromatic system.

There are two common isomers of naphthol: 1-naphthol (alpha-naphthol) and 2-naphthol (beta-naphthol). Consequently, their corresponding naphthoxide anions are 1-naphthoxide and 2-naphthoxide. The acidity of naphthols is influenced by the position of the hydroxyl group and the electronic properties of any substituents on the naphthalene ring. The naphthoxide anion is a resonance-stabilized species, with the negative charge being shared among several carbon atoms of the naphthalene ring and the oxygen atom.

Naphthoxides are typically prepared by reacting naphthols with a strong base, such as sodium hydroxide, potassium hydroxide, or alkali metal hydrides. These anions can act as nucleophiles in various organic reactions, including alkylation and acylation, leading to the formation of ethers and esters of naphthols, respectively. They also play roles in coordination chemistry as ligands for metal ions.