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Autoprotolysis
Type of molecular autoionization in which a hydron is transferred

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
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References

  1. 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