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In
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 ...
, an amphoteric compound () is a
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 ...
or ion that can react both as an
acid An acid is a molecule or ion capable of either donating a proton (i.e. Hydron, hydrogen cation, H+), known as a Brønsted–Lowry acid–base theory, Brønsted–Lowry acid, or forming a covalent bond with an electron pair, known as a Lewis ...
and as a base. What exactly this can mean depends on which definitions of acids and bases are being used.


Etymology and terminology

Amphoteric is derived from the Greek word () meaning "both". Related words in acid-base chemistry are amphichromatic and amphichroic, both describing substances such as acid-base indicators which give one colour on reaction with an acid and another colour on reaction with a base.


Amphiprotism

Amphiprotism is exhibited by compounds with both Brønsted acidic and basic properties. A prime example is H2O. Amphiprotic molecules can either donate or accept 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 ...
().
Amino acid Amino acids are organic compounds that contain both amino and carboxylic acid functional groups. Although over 500 amino acids exist in nature, by far the most important are the 22 α-amino acids incorporated into proteins. Only these 22 a ...
s (and
protein Proteins are large biomolecules and macromolecules that comprise one or more long chains of amino acid residue (biochemistry), residues. Proteins perform a vast array of functions within organisms, including Enzyme catalysis, catalysing metab ...
s) are amphiprotic molecules because of their
amine In chemistry, amines (, ) are organic compounds that contain carbon-nitrogen bonds. Amines are formed when one or more hydrogen atoms in ammonia are replaced by alkyl or aryl groups. The nitrogen atom in an amine possesses a lone pair of elec ...
() and
carboxylic acid In organic chemistry, a carboxylic acid is an organic acid that contains a carboxyl group () attached to an Substituent, R-group. The general formula of a carboxylic acid is often written as or , sometimes as with R referring to an organyl ...
() groups.


Ampholytes

Ampholytes are
zwitterion In chemistry, a zwitterion ( ; ), also called an inner salt or dipolar ion, is a molecule that contains an equal number of positively and negatively charged functional groups. : (1,2- dipolar compounds, such as ylides, are sometimes excluded from ...
s ‒ molecules or ions that contain both acidic and basic
functional group In organic chemistry, a functional group is any substituent or moiety (chemistry), moiety in a molecule that causes the molecule's characteristic chemical reactions. The same functional group will undergo the same or similar chemical reactions r ...
s.
Amino acid Amino acids are organic compounds that contain both amino and carboxylic acid functional groups. Although over 500 amino acids exist in nature, by far the most important are the 22 α-amino acids incorporated into proteins. Only these 22 a ...
s have both a basic group and an acidic group . Often such species exists as several structures in
chemical equilibrium In a chemical reaction, chemical equilibrium is the state in which both the Reagent, reactants and Product (chemistry), products are present in concentrations which have no further tendency to change with time, so that there is no observable chan ...
: : In approximately neutral
aqueous solution An aqueous solution is a solution in which the solvent is water. It is mostly shown in chemical equations by appending (aq) to the relevant chemical formula. For example, a solution of table salt, also known as sodium chloride (NaCl), in water ...
(pH ≅ 7), the basic amino group is mostly protonated and the carboxylic acid is mostly deprotonated, so that the predominant species is the
zwitterion In chemistry, a zwitterion ( ; ), also called an inner salt or dipolar ion, is a molecule that contains an equal number of positively and negatively charged functional groups. : (1,2- dipolar compounds, such as ylides, are sometimes excluded from ...
. The pH at which the average charge is zero is known as the molecule's ''
isoelectric point The isoelectric point (pI, pH(I), IEP), is the pH at which a molecule carries no net electric charge, electrical charge or is electrically neutral in the statistical mean. The standard nomenclature to represent the isoelectric point is pH(I). Howe ...
''. Ampholytes are used to establish a stable pH gradient for use in isoelectric focusing.
Metal oxide An oxide () is a chemical compound containing at least one oxygen atom and one other element in its chemical formula. "Oxide" itself is the dianion (anion bearing a net charge of −2) of oxygen, an O2− ion with oxygen in the oxidation state o ...
s which react with both acids as well as bases to produce salts and water are known as amphoteric oxides. Many metals (such as
zinc Zinc is a chemical element; it has symbol Zn and atomic number 30. It is a slightly brittle metal at room temperature and has a shiny-greyish appearance when oxidation is removed. It is the first element in group 12 (IIB) of the periodic tabl ...
,
tin Tin is a chemical element; it has symbol Sn () and atomic number 50. A silvery-colored metal, tin is soft enough to be cut with little force, and a bar of tin can be bent by hand with little effort. When bent, a bar of tin makes a sound, the ...
,
lead Lead () is a chemical element; it has Chemical symbol, symbol Pb (from Latin ) and atomic number 82. It is a Heavy metal (elements), heavy metal that is density, denser than most common materials. Lead is Mohs scale, soft and Ductility, malleabl ...
,
aluminium Aluminium (or aluminum in North American English) is a chemical element; it has chemical symbol, symbol Al and atomic number 13. It has a density lower than that of other common metals, about one-third that of steel. Aluminium has ...
, and
beryllium Beryllium is a chemical element; it has Symbol (chemistry), symbol Be and atomic number 4. It is a steel-gray, hard, strong, lightweight and brittle alkaline earth metal. It is a divalent element that occurs naturally only in combination with ...
) form amphoteric oxides or hydroxides.
Aluminium oxide Aluminium oxide (or aluminium(III) oxide) is a chemical compound of aluminium and oxygen with the chemical formula . It is the most commonly occurring of several Aluminium oxide (compounds), aluminium oxides, and specifically identified as alum ...
() is an example of an amphoteric oxide. Amphoterism depends on the
oxidation states In chemistry, the oxidation state, or oxidation number, is the hypothetical charge of an atom if all of its bonds to other atoms are fully ionic. It describes the degree of oxidation (loss of electrons) of an atom in a chemical compound. Concep ...
of the oxide. Amphoteric oxides include
lead(II) oxide Lead(II) oxide, also called lead monoxide, is the inorganic compound with the molecular formula Pb O. It occurs in two polymorphs: litharge having a tetragonal crystal structure, and massicot having an orthorhombic crystal structure. Modern ...
and
zinc oxide Zinc oxide is an inorganic compound with the Chemical formula, formula . It is a white powder which is insoluble in water. ZnO is used as an additive in numerous materials and products including cosmetics, Zinc metabolism, food supplements, rubbe ...
, among many others.


Amphiprotic molecules

According to the Brønsted-Lowry theory of acids and bases, acids are proton donors and bases are proton acceptors. An amphiprotic molecule (or ion) can either donate or accept 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 ...
, thus acting either as an
acid An acid is a molecule or ion capable of either donating a proton (i.e. Hydron, hydrogen cation, H+), known as a Brønsted–Lowry acid–base theory, Brønsted–Lowry acid, or forming a covalent bond with an electron pair, known as a Lewis ...
or a base.
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 ...
,
amino acid Amino acids are organic compounds that contain both amino and carboxylic acid functional groups. Although over 500 amino acids exist in nature, by far the most important are the 22 α-amino acids incorporated into proteins. Only these 22 a ...
s, hydrogencarbonate ion (or bicarbonate ion) ,
dihydrogen phosphate Dihydrogen phosphate is an inorganic ion with the formula 2PO4sup>−. Phosphates occur widely in natural systems. Perhaps the most common salt of dihydrogen phosphate is sodium dihydrogen phosphate. It is used in animal feed, fertilizer, ...
ion , and
hydrogensulfate The sulfate or sulphate ion is a polyatomic anion with the empirical formula . Salts, acid derivatives, and peroxides of sulfate are widely used in industry. Sulfates occur widely in everyday life. Sulfates are salts of sulfuric acid and many ...
ion (or bisulfate ion) are common examples of amphiprotic species. Since they can donate a proton, all amphiprotic substances contain a hydrogen atom. Also, since they can act like an acid or a base, they are amphoteric.


Examples

The water molecule is amphoteric in aqueous solution. It can either gain a proton to form a
hydronium In chemistry, hydronium (hydroxonium in traditional British English) is the cation , also written as , the type of oxonium ion produced by protonation of water. It is often viewed as the positive ion present when an Arrhenius acid is dissolved ...
ion , or else lose a proton to form a
hydroxide Hydroxide is a diatomic anion with chemical formula OH−. It consists of an oxygen and hydrogen atom held together by a single covalent bond, and carries a negative electric charge. It is an important but usually minor constituent of water. It ...
ion . Another possibility is the
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 ...
reaction between two water molecules, in which one water molecule acts as an acid and another as a base. : The
bicarbonate In inorganic chemistry, bicarbonate (IUPAC-recommended nomenclature: hydrogencarbonate) is an intermediate form in the deprotonation of carbonic acid. It is a polyatomic anion with the chemical formula . Bicarbonate serves a crucial bioche ...
ion, , is amphoteric as it can act as either an acid or a base: :As an acid, losing a proton: :As a base, accepting a proton: Note: in dilute aqueous solution the formation of the
hydronium ion In chemistry, hydronium (hydroxonium in traditional British English) is the cation , also written as , the type of oxonium ion produced by protonation of water. It is often viewed as the positive ion present when an Arrhenius acid is dissolved in ...
, , is effectively complete, so that hydration of the proton can be ignored in relation to the equilibria. Other examples of inorganic polyprotic acids include anions of
sulfuric acid Sulfuric acid (American spelling and the preferred IUPAC name) or sulphuric acid (English in the Commonwealth of Nations, Commonwealth spelling), known in antiquity as oil of vitriol, is a mineral acid composed of the elements sulfur, oxygen, ...
,
phosphoric acid Phosphoric acid (orthophosphoric acid, monophosphoric acid or phosphoric(V) acid) is a colorless, odorless phosphorus-containing solid, and inorganic compound with the chemical formula . It is commonly encountered as an 85% aqueous solution, ...
and
hydrogen sulfide Hydrogen sulfide is a chemical compound with the formula . It is a colorless chalcogen-hydride gas, and is toxic, corrosive, and flammable. Trace amounts in ambient atmosphere have a characteristic foul odor of rotten eggs. Swedish chemist ...
that have lost one or more protons. In organic chemistry and biochemistry, important examples include
amino acid Amino acids are organic compounds that contain both amino and carboxylic acid functional groups. Although over 500 amino acids exist in nature, by far the most important are the 22 α-amino acids incorporated into proteins. Only these 22 a ...
s and derivatives of
citric acid Citric acid is an organic compound with the formula . It is a Transparency and translucency, colorless Weak acid, weak organic acid. It occurs naturally in Citrus, citrus fruits. In biochemistry, it is an intermediate in the citric acid cycle, ...
. Although an amphiprotic species must be amphoteric, the converse is not true. For example, a metal oxide such as
zinc oxide Zinc oxide is an inorganic compound with the Chemical formula, formula . It is a white powder which is insoluble in water. ZnO is used as an additive in numerous materials and products including cosmetics, Zinc metabolism, food supplements, rubbe ...
, ZnO, contains no hydrogen and so cannot donate a proton. Nevertheless, it can act as an acid by reacting with the hydroxide ion, a base: : Zinc oxide can also act as a base: :


Oxides

Zinc oxide Zinc oxide is an inorganic compound with the Chemical formula, formula . It is a white powder which is insoluble in water. ZnO is used as an additive in numerous materials and products including cosmetics, Zinc metabolism, food supplements, rubbe ...
(ZnO) reacts both with acids and with bases: *ZnO + \overset -> ZnSO4 + H2O *ZnO + \overset + H2O -> Na2 n(OH)4/chem> This reactivity can be used to separate different
cation An ion () is an atom or molecule with a net electrical charge. The charge of an electron is considered to be negative by convention and this charge is equal and opposite to the charge of a proton, which is considered to be positive by convent ...
s, for instance zinc(II), which dissolves in base, from manganese(II), which does not dissolve in base.
Lead oxide Lead oxides are a group of inorganic compounds with formulas including lead (Pb) and oxygen Oxygen is a chemical element; it has chemical symbol, symbol O and atomic number 8. It is a member of the chalcogen group (periodic table), gr ...
(PbO): * PbO + \overset -> PbCl2 + H2O * PbO + \overset + H2O -> Na2 b(OH)4/chem>
Lead oxide Lead oxides are a group of inorganic compounds with formulas including lead (Pb) and oxygen Oxygen is a chemical element; it has chemical symbol, symbol O and atomic number 8. It is a member of the chalcogen group (periodic table), gr ...
(): * PbO2 + \overset -> PbCl4 + 2H2O * PbO2 + \overset + 2H2O -> Na2 b(OH)6/chem>
Aluminium oxide Aluminium oxide (or aluminium(III) oxide) is a chemical compound of aluminium and oxygen with the chemical formula . It is the most commonly occurring of several Aluminium oxide (compounds), aluminium oxides, and specifically identified as alum ...
(): * Al2O3 + \overset -> 2 AlCl3 + 3 H2O * Al2O3 + \overset + 3 H2O -> 2 Na l(OH)4/chem> (hydrated sodium aluminate)
Stannous oxide Tin(II) oxide (stannous oxide) is a compound with the formula SnO. It is composed of tin and oxygen where tin has the oxidation state of +2. There are two forms, a stable blue-black form and a metastable red form. Preparation and reactions Blu ...
(SnO): * SnO + \overset <=> SnCl2 + H2O * SnO + \overset + H2O <=> Na4 n(OH)6/chem> Stannic oxide (): * SnO2 + \overset <=> SnCl4 + 2H2O * SnO2 + \overset + 2H2O <=> Na4 n(OH)8/chem> Vanadium dioxide (): *VO2 + \overset -> VOCl2 + H2O *4 VO2 + \overset -> Na2V4O9 + H2O Some other elements which form amphoteric oxides are
gallium Gallium is a chemical element; it has Chemical symbol, symbol Ga and atomic number 31. Discovered by the French chemist Paul-Émile Lecoq de Boisbaudran in 1875, elemental gallium is a soft, silvery metal at standard temperature and pressure. ...
,
indium Indium is a chemical element; it has Symbol (chemistry), symbol In and atomic number 49. It is a silvery-white post-transition metal and one of the softest elements. Chemically, indium is similar to gallium and thallium, and its properties are la ...
,
scandium Scandium is a chemical element; it has Symbol (chemistry), symbol Sc and atomic number 21. It is a silvery-white metallic d-block, d-block element. Historically, it has been classified as a rare-earth element, together with yttrium and the lantha ...
,
titanium Titanium is a chemical element; it has symbol Ti and atomic number 22. Found in nature only as an oxide, it can be reduced to produce a lustrous transition metal with a silver color, low density, and high strength, resistant to corrosion in ...
,
zirconium Zirconium is a chemical element; it has Symbol (chemistry), symbol Zr and atomic number 40. First identified in 1789, isolated in impure form in 1824, and manufactured at scale by 1925, pure zirconium is a lustrous transition metal with a greyis ...
,
chromium Chromium is a chemical element; it has Symbol (chemistry), symbol Cr and atomic number 24. It is the first element in Group 6 element, group 6. It is a steely-grey, Luster (mineralogy), lustrous, hard, and brittle transition metal. Chromium ...
,
iron Iron is a chemical element; it has symbol Fe () and atomic number 26. It is a metal that belongs to the first transition series and group 8 of the periodic table. It is, by mass, the most common element on Earth, forming much of Earth's o ...
,
cobalt Cobalt is a chemical element; it has Symbol (chemistry), symbol Co and atomic number 27. As with nickel, cobalt is found in the Earth's crust only in a chemically combined form, save for small deposits found in alloys of natural meteoric iron. ...
,
copper Copper is a chemical element; it has symbol Cu (from Latin ) and atomic number 29. It is a soft, malleable, and ductile metal with very high thermal and electrical conductivity. A freshly exposed surface of pure copper has a pinkish-orang ...
,
silver Silver is a chemical element; it has Symbol (chemistry), symbol Ag () and atomic number 47. A soft, whitish-gray, lustrous transition metal, it exhibits the highest electrical conductivity, thermal conductivity, and reflectivity of any metal. ...
,
gold Gold is a chemical element; it has chemical symbol Au (from Latin ) and atomic number 79. In its pure form, it is a brightness, bright, slightly orange-yellow, dense, soft, malleable, and ductile metal. Chemically, gold is a transition metal ...
,
germanium Germanium is a chemical element; it has Symbol (chemistry), symbol Ge and atomic number 32. It is lustrous, hard-brittle, grayish-white and similar in appearance to silicon. It is a metalloid or a nonmetal in the carbon group that is chemically ...
,
antimony Antimony is a chemical element; it has chemical symbol, symbol Sb () and atomic number 51. A lustrous grey metal or metalloid, it is found in nature mainly as the sulfide mineral stibnite (). Antimony compounds have been known since ancient t ...
,
bismuth Bismuth is a chemical element; it has symbol Bi and atomic number 83. It is a post-transition metal and one of the pnictogens, with chemical properties resembling its lighter group 15 siblings arsenic and antimony. Elemental bismuth occurs nat ...
,
beryllium Beryllium is a chemical element; it has Symbol (chemistry), symbol Be and atomic number 4. It is a steel-gray, hard, strong, lightweight and brittle alkaline earth metal. It is a divalent element that occurs naturally only in combination with ...
, and
tellurium Tellurium is a chemical element; it has symbol Te and atomic number 52. It is a brittle, mildly toxic, rare, silver-white metalloid. Tellurium is chemically related to selenium and sulfur, all three of which are chalcogens. It is occasionally fou ...
.


Hydroxides

Aluminium hydroxide Aluminium hydroxide, , is found as the mineral gibbsite (also known as hydrargillite) and its three much rarer polymorphs: bayerite, doyleite, and nordstrandite. Aluminium hydroxide is amphoteric, i.e., it has both basic and acidic propert ...
is also amphoteric: *Al(OH)3 + \overset -> AlCl3 + 3 H2O *Al(OH)3 + \overset -> Na l(OH)4/chem> Beryllium hydroxide: *Be(OH)2 + \overset -> BeCl2 + 2 H2O *Be(OH)2 + \overset -> Na2 e(OH)4/chem>CHEMIX School & Lab - Software for Chemistry Learning, by Arne Standnes
(program download required) Chromium hydroxide: *Cr(OH)3 + \overset -> CrCl3 + 3H2O *Cr(OH)3 + \overset -> Na r(OH)4/chem>


See also

* Ate complex *
Isoelectric point The isoelectric point (pI, pH(I), IEP), is the pH at which a molecule carries no net electric charge, electrical charge or is electrically neutral in the statistical mean. The standard nomenclature to represent the isoelectric point is pH(I). Howe ...
*
Zwitterion In chemistry, a zwitterion ( ; ), also called an inner salt or dipolar ion, is a molecule that contains an equal number of positively and negatively charged functional groups. : (1,2- dipolar compounds, such as ylides, are sometimes excluded from ...


References

{{Reflist Acid–base chemistry Chemical properties General chemistry