In chemistry, autoprotolysis is a molecular autoionization, a chemical reaction in which a proton is transferred between two identical molecules, one of which acts as a Brønsted acid, releasing a proton that is accepted by the other molecule, which acts as a Brønsted base. Any chemical that contains both acidic hydrogen and lone pairs of electrons to accept H+ can undergo autoprotolysis.
For example, water undergoes autoprotolysis in the self-ionization of water reaction.
2 H2O ⇌ OH− + H3O+For example, ammonia in its purest form may undergo autoprotolysis:
2 NH3 ⇌ NH−2 + NH+4Another example is acetic acid:
2 CH3COOH ⇌ CH3COO− + CH3COOH+2References
IUPAC, Compendium of Chemical Terminology, 2nd ed. (the "Gold Book") (1997). Online corrected version: (2006–) "autoprotolysis". doi:10.1351/goldbook.A00531 /wiki/International_Union_of_Pure_and_Applied_Chemistry ↩