chemistry Chemistry is the scientific study of the properties and behavior of matter. It is a physical science within the natural sciences that studies the chemical elements that make up matter and chemical compound, compounds made of atoms, molecules a ...

, autoprotolysis is a

molecular autoionization In chemistry, molecular autoionization (or self-ionization) is a chemical reaction between molecules of the same substance to produce ions. If a pure liquid partially dissociates into ions, it is said to be self-ionizing. In most cases the ox ...

, a

chemical reaction A chemical reaction is a process that leads to the chemistry, chemical transformation of one set of chemical substances to another. When chemical reactions occur, the atoms are rearranged and the reaction is accompanied by an Gibbs free energy, ...

in which a

proton A proton is a stable subatomic particle, symbol , Hydron (chemistry), H+, or 1H+ with a positive electric charge of +1 ''e'' (elementary charge). Its mass is slightly less than the mass of a neutron and approximately times the mass of an e ...

is transferred between two identical

molecule A molecule is a group of two or more atoms that are held together by Force, attractive forces known as chemical bonds; depending on context, the term may or may not include ions that satisfy this criterion. In quantum physics, organic chemi ...

s, 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 can undergo autoprotolysis. For example,

water Water is an inorganic compound with the chemical formula . It is a transparent, tasteless, odorless, and Color of water, nearly colorless chemical substance. It is the main constituent of Earth's hydrosphere and the fluids of all known liv ...

undergoes autoprotolysis in the

self-ionization of water The self-ionization of water (also autoionization of water, autoprotolysis of water, autodissociation of water, or simply dissociation of water) is an ionization reaction in properties of water, pure water or in an aqueous solution, in which a wa ...

reaction. : For example,

ammonia Ammonia is an inorganic chemical compound of nitrogen and hydrogen with the chemical formula, formula . A Binary compounds of hydrogen, stable binary hydride and the simplest pnictogen hydride, ammonia is a colourless gas with a distinctive pu ...

in its purest form may undergo autoprotolysis: : Another example is

acetic acid Acetic acid , systematically named ethanoic acid , is an acidic, colourless liquid and organic compound with the chemical formula (also written as , , or ). Vinegar is at least 4% acetic acid by volume, making acetic acid the main compone ...

: :

References

Acid–base chemistry Equilibrium chemistry {{analytical-chemistry-stub