\( \require{mhchem} \)
In chemistry, autoprotolysis is a chemical reaction in which 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.
\( {\displaystyle {\ce {2H2O <=> OH- + H3O+}}} \)
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:
\( {\displaystyle {\ce {2NH3 <=> NH2- + NH4+}}} \)
Another example is acetic acid:
\( {\displaystyle {\ce {2CH3COOH <=> CH3COO- + CH3COOH2+}}} \)
References
IUPAC, Compendium of Chemical Terminology, 2nd ed. (the "Gold Book") (1997). Online corrected version: (2006–) "autoprotolysis". doi:10.1351/goldbook.A00531
Hellenica World - Scientific Library
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