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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+4

Another example is acetic acid:

2 CH₃COOH ⇌ CH₃COO + CH₃COOH+2

References

1. IUPAC, Compendium of Chemical Terminology, 2nd ed. (the "Gold Book") (1997). Online corrected version: (2006–) "autoprotolysis". doi:10.1351/goldbook.A00531

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