Autoprotolysis

In autoprotolysis a proton is transferred between two identical molecules, one of which acts as a Brønsted acid, releasing a proton which is accepted by the other molecule acting as a Brønsted base.[1] For example, water undergoes autoprotolysis in the self-ionization of water reaction. It is a type of molecular autoionization.

2H
2O ⇌ OH−
 + H
3O+

Any solvent that contains both acidic hydrogen and lone pairs of electrons to accept H+ can undergo autoprotolysis.

For example, ammonia in its purest form may undergo autoprotolysis:

2NH
3 ⇌ NH−
2 + NH+
4

Another example is acetic acid:

2CH
3COOH ⇌ CH
3COO−
 + CH
3COOH+
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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