phenoxide

The sodium salt of phenol, sodium phenoxide, is far more water soluble.

"Trade name for thallium phenoxide."

Since phenols are acidic, they readily react with a strong base like sodium hydroxide to form phenoxide ions.

Finally, the phenoxide extracts the acidic hydrogen from the carboxylic acid, yielding the collected products (6).

Attack of the phenoxide on the ester grouping leads to cyclization and formation of the coumarin.

One explanation for the increased acidity over alcohols is resonance stabilization of the phenoxide anion by the aromatic ring.

If the phenoxide oxygen is oxidized, the semiquinone is formed with the unpaired electron being located on the ring.

The reactive species is the phenoxide anion (CHO) formed by deprotonation of phenol.

When phenol is deprotonated, the resulting phenoxide anion is such that its negative charge can be delocalized to several positions on the phenyl ring.

The reaction is performed in cold THF, and the sensitive nitro, azo and phenoxide groups all survive intact.

Anisole is prepared by the Williamson ether synthesis, reacting sodium phenoxide with methyl bromide and related methylating reagents:

It is treated with dilute sodium hydroxide at 350 C and 300 bar to convert it to sodium phenoxide, which yields phenol upon acidification.

When ubiquinol binds to cytochrome b, the pKa of the phenolic group decreases so that the proton ionizes and the phenoxide anion is formed.

He moved furtively, like a six-foot mouse with thallium phenoxide poisoning, jerking his head around as if to look for right-wing death squads and CIA snipers.

Phenol is weakly acidic but at high pH's gives the phenolate anion CHO (also called phenoxide):

Under normal circumstances, phenoxide is more reactive at the oxygen position, but the oxygen position is a "hard" nucleophile whereas the alpha-carbon positions tend to be "soft".

The position of the equilibrium can be controlled by the acidity of the alcohol; for example phenols typically react with alkoxides to release alcohols, giving the corresponding phenoxide.

The conjugation also greatly reduces the basicity of the oxygens and the nitrogen, while making the hydroxyl acidic through delocalisation of charge developed on the phenoxide anion.

Halogenation of phenols is faster in polar solvents due to the dissociation of phenol, with phenoxide ions being more susceptible to electrophilic attack as they are more electron-rich.

The phenoxide ion will then substitute the -X group in the alkyl halide, forming an ether with an aryl group attached to it in a reaction with an SN2 mechanism.

The di phenoxide ((NaOCH)CMe) reacts with phosgene to give a chloroformate, which subsequently is attacked by another phenoxide.

In these examples, the base (KCO or LiCO) removes the acidic proton to form the carboxylate or phenoxide anion, which serves as the nucleophile in the S2 substitution.

The phenoxide anion has a similar nucleophilicity to free amines, with the further advantage that its conjugate acid (neutral phenol) does not become entirely deactivated as a nucleophile even in moderately acidic conditions.

The phenyl ester is subsequently hydrolyzed: nucleophilic addition of hydroxide from solution to the ester carbonyl carbon forms a second tetrahedral intermediate (4), which collapses, eliminating a phenoxide and forming a carboxylic acid (5).

Loss of a positive hydrogen ion (H) from the hydroxyl group of a phenol forms a corresponding negative phenolate ion or phenoxide ion, and the corresponding salts are called phenolates or phenoxides, although the term aryloxides is preferred according to the IUPAC Gold Book.