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. For example, water undergoes autoprotolysis in the self-ionization of water reaction.

2H
2
O
OH
+ H
3
O+

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

References

Autoprotolysis. IUPAC gold book. doi:10.1351/goldbook.A00531. 

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