Alkali metal phenolates, such as
sodium phenolate hydrolyze in aqueous solution to form basic solutions. At pH = 10, phenol and phenolate are in approximately 1:1 proportions. The phenoxide anion (aka
phenolate) is a strong
nucleophile with a comparable to the one of carbanions or tertiary amines. Generally, oxygen attack of phenoxide anions is kinetically favored, while carbon-attack is thermodynamically preferred (see
Thermodynamic versus kinetic reaction control). Mixed oxygen/carbon attack and by this a loss of selectivity is usually observed if the reaction rate reaches diffusion control. == Uses ==