Olation
At low pH, many metal ions exist in aqueous solution as aqua coordination complexes, often with the formula [M(HO)]. As the pH increases, one O-H bond ionizes to give the hydroxide complex, the conjugate base of the parent hexaaqua complex:
The hydroxo complex is poised to undergo olation, which is initiated by displacement of one water by a neighboring complex:
In this product, the hydroxide ligand bridges between the two metals, this bridge is denoted with the symbol μ.
In the resulting 5+ ion, the remaining water and hydroxo ligands are highly acidic and the ionization and condensation processes can continue at still higher pHs. The formation of the oxo-dimer is a process called "oxolation," although sometimes olation and oxolation are not distinguished:
Ultimately one observes the formation of the metal oxide:
Hydroxide
Other cases where hydroxide can act as a nucleophilic reagent are amide hydrolysis, the Cannizzaro reaction, nucleophilic aliphatic substitution, nucleophilic aromatic substitution, and in elimination reactions. The reaction medium for KOH and NaOH is usually water but with a phase-transfer catalyst the hydroxide anion can be shuttled into an organic solvent as well, for example in the generation of the reactive intermediate dichlorocarbene.