Oxo Acid
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An oxyacid, oxoacid, or ternary acid is an
acid In computer science, ACID ( atomicity, consistency, isolation, durability) is a set of properties of database transactions intended to guarantee data validity despite errors, power failures, and other mishaps. In the context of databases, a sequ ...
that contains
oxygen Oxygen is the chemical element with the symbol O and atomic number 8. It is a member of the chalcogen group in the periodic table, a highly reactive nonmetal, and an oxidizing agent that readily forms oxides with most elements as wel ...
. Specifically, it is a compound that contains hydrogen, oxygen, and at least one other element, with at least one
hydrogen Hydrogen is the chemical element with the symbol H and atomic number 1. Hydrogen is the lightest element. At standard conditions hydrogen is a gas of diatomic molecules having the formula . It is colorless, odorless, tasteless, non-toxic, an ...
atom bonded to oxygen that can dissociate to produce the H+ cation and the
anion 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 ...
of the acid.


Description

Under Lavoisier's original theory, all acids contained oxygen, which was named from the Greek ὀξύς (''oxys'': acid, sharp) and the root -γενής (''-genes'': creator). It was later discovered that some acids, notably
hydrochloric acid Hydrochloric acid, also known as muriatic acid, is an aqueous solution of hydrogen chloride. It is a colorless solution with a distinctive pungent smell. It is classified as a strong acid Acid strength is the tendency of an acid, symbol ...
, did not contain oxygen and so acids were divided into oxo-acids and these new hydroacids. All oxyacids have the acidic hydrogen bound to an oxygen atom, so bond strength (length) is not a factor, as it is with binary nonmetal hydrides. Rather, the electronegativity of the central atom and the number of oxygen atoms determine oxyacid acidity. For oxyacids with the same central atom, acid strength increases with the number of oxygen atoms attached to it. With the same number of oxygen atoms attached to it, acid strength increases with increasing electronegativity of the central atom. Compared to the salts of their deprotonated forms (a class of compounds known as the oxyanions), oxyacids are generally less stable, and many of them only exist formally as hypothetical species, or only exist in solution and cannot be isolated in pure form. There are several general reasons for this: (1) they may condense to form
oligomer In chemistry and biochemistry, an oligomer () is a molecule that consists of a few repeating units which could be derived, actually or conceptually, from smaller molecules, monomers.Quote: ''Oligomer molecule: A molecule of intermediate relativ ...
s (e.g., H2CrO4 to H2Cr2O7), or dehydrate all the way to form the anhydride (e.g., H2CO3 to CO2), (2) they may disproportionate to one compound of higher and another of lower oxidation state (e.g., HClO2 to HClO and HClO3), or (3) they might exist almost entirely as another, more stable
tautomer Tautomers () are structural isomers (constitutional isomers) of chemical compounds that readily interconvert. The chemical reaction interconverting the two is called tautomerization. This conversion commonly results from the relocation of a hydr ...
ic form (e.g., phosphorous acid P(OH)3 exists almost entirely as phosphonic acid HP(=O)(OH)2). Nevertheless, perchloric acid (HClO4), sulfuric acid (H2SO4), and nitric acid (HNO3) are a few common oxyacids that are relatively easily prepared as pure substances.
Imidic acid In chemistry, an imidic acid is any molecule that contains the -C(=NH)-OH functional group. It is the tautomer of an amide and the isomer of an oxime. The term "imino acid" is an obsolete term for this group that should not be used in this contex ...
s are created by replacing =O with =NR in an oxyacid.


Properties

An oxyacid molecule contains the structure X−O−H, where other atoms or atom groups can be connected to the central atom X. In a
solution Solution may refer to: * Solution (chemistry), a mixture where one substance is dissolved in another * Solution (equation), in mathematics ** Numerical solution, in numerical analysis, approximate solutions within specified error bounds * Soluti ...
, such a molecule can be dissociated into
ion 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 conven ...
s in two distinct ways: * X−O−H ⇄ (X−O) + H+ * X−O−H ⇄ X+ + OH If the central atom X is strongly
electronegative Electronegativity, symbolized as , is the tendency for an atom of a given chemical element to attract shared electrons (or electron density) when forming a chemical bond. An atom's electronegativity is affected by both its atomic number and the d ...
, then it strongly attracts the
electron The electron ( or ) is a subatomic particle with a negative one elementary electric charge. Electrons belong to the first generation of the lepton particle family, and are generally thought to be elementary particles because they have no kn ...
s of the oxygen atom. In that case, the bond between the oxygen and hydrogen atom is weak, and the compound ionizes easily in the way of the former of the two chemical equations above. In this case, the compound XOH is an acid, because it releases a
proton A proton is a stable subatomic particle, symbol , H+, or 1H+ with a positive electric charge of +1 ''e'' elementary charge. Its mass is slightly less than that of a neutron and 1,836 times the mass of an electron (the proton–electron mass ...
, that is, a hydrogen ion. For example,
nitrogen Nitrogen is the chemical element with the symbol N and atomic number 7. Nitrogen is a nonmetal and the lightest member of group 15 of the periodic table, often called the pnictogens. It is a common element in the universe, estimated at se ...
,
sulfur Sulfur (or sulphur in British English) is a chemical element with the symbol S and atomic number 16. It is abundant, multivalent and nonmetallic. Under normal conditions, sulfur atoms form cyclic octatomic molecules with a chemical formula ...
and
chlorine Chlorine is a chemical element with the Symbol (chemistry), symbol Cl and atomic number 17. The second-lightest of the halogens, it appears between fluorine and bromine in the periodic table and its properties are mostly intermediate betwee ...
are strongly electronegative elements, and therefore
nitric acid Nitric acid is the inorganic compound with the formula . It is a highly corrosive mineral acid. The compound is colorless, but older samples tend to be yellow cast due to decomposition into oxides of nitrogen. Most commercially available nitri ...
,
sulfuric acid Sulfuric acid (American spelling and the preferred IUPAC name) or sulphuric acid ( Commonwealth spelling), known in antiquity as oil of vitriol, is a mineral acid composed of the elements sulfur, oxygen and hydrogen, with the molecular formu ...
, and
perchloric acid Perchloric acid is a mineral acid with the formula H Cl O4. Usually found as an aqueous solution, this colorless compound is a stronger acid than sulfuric acid, nitric acid and hydrochloric acid. It is a powerful oxidizer when hot, but aqueous sol ...
, are strong acids. If, however, the electronegativity of X is low, then the compound is dissociated to ions according to the latter chemical equation, and XOH is an
alkaline In chemistry, an alkali (; from ar, القلوي, al-qaly, lit=ashes of the saltwort) is a base (chemistry), basic, ionic compound, ionic salt (chemistry), salt of an alkali metal or an alkaline earth metal. An alkali can also be defined as ...
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. I ...
. Examples of such compounds are
sodium hydroxide Sodium hydroxide, also known as lye and caustic soda, is an inorganic compound with the formula NaOH. It is a white solid ionic compound consisting of sodium cations and hydroxide anions . Sodium hydroxide is a highly caustic base and alkali ...
NaOH and
calcium hydroxide Calcium hydroxide (traditionally called slaked lime) is an inorganic compound with the chemical formula Ca( OH)2. It is a colorless crystal or white powder and is produced when quicklime (calcium oxide) is mixed or slaked with water. It has m ...
Ca(OH)2. Owing to the high electronegativity of oxygen, however, most of the common oxobases, such as sodium hydroxide, while strongly basic in water, are only moderately basic in comparison to other bases. For example, the pKa of the conjugate acid of
sodium hydroxide Sodium hydroxide, also known as lye and caustic soda, is an inorganic compound with the formula NaOH. It is a white solid ionic compound consisting of sodium cations and hydroxide anions . Sodium hydroxide is a highly caustic base and alkali ...
,
water Water (chemical formula ) is an inorganic, transparent, tasteless, odorless, and nearly colorless chemical substance, which is the main constituent of Earth's hydrosphere and the fluids of all known living organisms (in which it acts as a ...
, is 15.7, while that of sodium amide,
ammonia Ammonia is an inorganic compound of nitrogen and hydrogen with the formula . A stable binary hydride, and the simplest pnictogen hydride, ammonia is a colourless gas with a distinct pungent smell. Biologically, it is a common nitrogenous was ...
, is closer to 40, making sodium hydroxide a much weaker base than sodium amide. If the electronegativity of X is somewhere in between, the compound can be amphoteric, and in that case it can dissociate to ions in both ways, in the former case when reacting with bases, and in the latter case when reacting with acids. Examples of this include aliphatic
alcohols In chemistry, an alcohol is a type of organic compound that carries at least one hydroxyl () functional group bound to a saturated carbon atom. The term ''alcohol'' originally referred to the primary alcohol ethanol (ethyl alcohol), which is ...
, such as
ethanol Ethanol (abbr. EtOH; also called ethyl alcohol, grain alcohol, drinking alcohol, or simply alcohol) is an organic compound. It is an Alcohol (chemistry), alcohol with the chemical formula . Its formula can be also written as or (an ethyl ...
. Inorganic oxyacids typically have a chemical formula of type H''m''XO''n'', where X is an atom functioning as a ''central atom'', whereas parameters ''m'' and ''n'' depend on the
oxidation state In chemistry, the oxidation state, or oxidation number, is the hypothetical charge of an atom if all of its bonds to different atoms were fully ionic. It describes the degree of oxidation (loss of electrons) of an atom in a chemical compound. C ...
of the element X. In most cases, the element ''X'' is a
nonmetal In chemistry, a nonmetal is a chemical element that generally lacks a predominance of metallic properties; they range from colorless gases (like hydrogen) to shiny solids (like carbon, as graphite). The electrons in nonmetals behave differentl ...
, but some
metal A metal (from Greek μέταλλον ''métallon'', "mine, quarry, metal") is a material that, when freshly prepared, polished, or fractured, shows a lustrous appearance, and conducts electricity and heat relatively well. Metals are typicall ...
s, for example
chromium Chromium is a chemical element with the symbol Cr and atomic number 24. It is the first element in group 6. It is a steely-grey, lustrous, hard, and brittle transition metal. Chromium metal is valued for its high corrosion resistance and hardne ...
and
manganese Manganese is a chemical element with the symbol Mn and atomic number 25. It is a hard, brittle, silvery metal, often found in minerals in combination with iron. Manganese is a transition metal with a multifaceted array of industrial alloy use ...
, can form oxyacids when occurring at their highest
oxidation state In chemistry, the oxidation state, or oxidation number, is the hypothetical charge of an atom if all of its bonds to different atoms were fully ionic. It describes the degree of oxidation (loss of electrons) of an atom in a chemical compound. C ...
s.Kivinen, Mäkitie: Kemia, p. 202-203, chapter=Happihapot When oxyacids are heated, many of them dissociate to water and the anhydride of the acid. In most cases, such anhydrides are
oxide An oxide () is a chemical compound that contains at least one oxygen atom and one other element in its chemical formula. "Oxide" itself is the dianion of oxygen, an O2– (molecular) ion. with oxygen in the oxidation state of −2. Most of the E ...
s of nonmetals. For example,
carbon dioxide Carbon dioxide (chemical formula ) is a chemical compound made up of molecules that each have one carbon atom covalently double bonded to two oxygen atoms. It is found in the gas state at room temperature. In the air, carbon dioxide is transpar ...
, CO2, is the anhydride of carbonic acid, H2CO3, and
sulfur trioxide Sulfur trioxide (alternative spelling sulphur trioxide, also known as ''nisso sulfan'') is the chemical compound with the formula SO3. It has been described as "unquestionably the most important economically" sulfur oxide. It is prepared on an ind ...
, SO3, is the anhydride of
sulfuric acid Sulfuric acid (American spelling and the preferred IUPAC name) or sulphuric acid ( Commonwealth spelling), known in antiquity as oil of vitriol, is a mineral acid composed of the elements sulfur, oxygen and hydrogen, with the molecular formu ...
, H2SO4. These anhydrides react quickly with water and form those oxyacids again. Many
organic acid An organic acid is an organic compound with acidic properties. The most common organic acids are the carboxylic acids, whose acidity is associated with their carboxyl group –COOH. Sulfonic acids, containing the group –SO2OH, are rel ...
s, like
carboxylic acid In organic chemistry, a carboxylic acid is an organic acid that contains a carboxyl group () attached to an R-group. The general formula of a carboxylic acid is or , with R referring to the alkyl, alkenyl, aryl, or other group. Carboxylic ...
s and
phenol Phenol (also called carbolic acid) is an aromatic organic compound with the molecular formula . It is a white crystalline solid that is volatile. The molecule consists of a phenyl group () bonded to a hydroxy group (). Mildly acidic, it req ...
s, are oxyacids. Their molecular structure, however, is much more complicated than that of inorganic oxyacids. Most of the commonly encountered acids are oxyacids. Indeed, in the 18th century,
Lavoisier Antoine-Laurent de Lavoisier ( , ; ; 26 August 17438 May 1794),
CNRS (
Greek and meaning ''acid-maker'', which is still, in a more or less modified form, used in most languages. Later, however,
Humphry Davy Sir Humphry Davy, 1st Baronet, (17 December 177829 May 1829) was a British chemist and inventor who invented the Davy lamp and a very early form of arc lamp. He is also remembered for isolating, by using electricity, several elements for t ...
showed that the so-called muriatic acid did not contain oxygen, despite its being a strong acid; instead, it is a solution of
hydrogen chloride The compound hydrogen chloride has the chemical formula and as such is a hydrogen halide. At room temperature, it is a colourless gas, which forms white fumes of hydrochloric acid upon contact with atmospheric water vapor. Hydrogen chloride ga ...
, HCl.Otavan suuri Ensyklopedia, s. 1605, art. Hapot ja emäxet Such acids which do not contain oxygen are nowadays known as hydroacids.


Names of inorganic oxyacids

Many inorganic oxyacids are traditionally called with names ending with the word ''acid'' and which also contain, in a somewhat modified form, the name of the element they contain in addition to hydrogen and oxygen. Well-known examples of such acids are
sulfuric acid Sulfuric acid (American spelling and the preferred IUPAC name) or sulphuric acid ( Commonwealth spelling), known in antiquity as oil of vitriol, is a mineral acid composed of the elements sulfur, oxygen and hydrogen, with the molecular formu ...
,
nitric acid Nitric acid is the inorganic compound with the formula . It is a highly corrosive mineral acid. The compound is colorless, but older samples tend to be yellow cast due to decomposition into oxides of nitrogen. Most commercially available nitri ...
and phosphoric acid. This practice is fully well-established, and
IUPAC The International Union of Pure and Applied Chemistry (IUPAC ) is an international federation of National Adhering Organizations working for the advancement of the chemical sciences, especially by developing nomenclature and terminology. It is ...
has accepted such names. In light of the current
chemical nomenclature A chemical nomenclature is a set of rules to generate systematic names for chemical compounds. The nomenclature used most frequently worldwide is the one created and developed by the International Union of Pure and Applied Chemistry (IUPAC). The ...
, this practice is an exception, because systematic names of compounds are formed according to the elements they contain and their molecular structure, not according to other properties (for example, acidity) they have.Red Book 2005, s. 124, chapter IR-8: Inorganic Acids and Derivatives IUPAC, however, recommends against calling future compounds not yet discovered with a name ending with the word ''acid''. Indeed, acids can be called with names formed by adding the word ''hydrogen'' in front of the corresponding
anion 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 ...
; for example, sulfuric acid could just as well be called ''hydrogen sulfate'' (or ''dihydrogen sulfate'').Kivinen, Mäkitie: Kemia, p. 459-461, chapter Kemian nimistö: Hapot In fact, the fully systematic name of sulfuric acid, according to IUPAC's rules, would be ''dihydroxidodioxidosulfur'' and that of the sulfate ion, ''tetraoxidosulfate(2−)'',Red Book 2005, p. 129-132, table IR-8-1 Such names, however, are almost never used. However, the same element can form more than one acid when compounded with hydrogen and oxygen. In such cases, the
English English usually refers to: * English language * English people English may also refer to: Peoples, culture, and language * ''English'', an adjective for something of, from, or related to England ** English national ide ...
practice to distinguish such acids is to use the suffix ''-ic'' in the name of the element in the name of the acid containing more oxygen atoms, and the suffix ''-ous'' in the name of the element in the name of the acid containing fewer oxygen atoms. Thus, for example,
sulfuric acid Sulfuric acid (American spelling and the preferred IUPAC name) or sulphuric acid ( Commonwealth spelling), known in antiquity as oil of vitriol, is a mineral acid composed of the elements sulfur, oxygen and hydrogen, with the molecular formu ...
is H2SO4, and
sulfurous acid Sulfurous acid (also sulfuric(IV) acid, sulphurous acid (UK), sulphuric(IV) acid (UK)) is the chemical compound with the formula . There is no evidence that sulfurous acid exists in solution, but the molecule has been detected in the gas phase. ...
, H2SO3. Analogously,
nitric acid Nitric acid is the inorganic compound with the formula . It is a highly corrosive mineral acid. The compound is colorless, but older samples tend to be yellow cast due to decomposition into oxides of nitrogen. Most commercially available nitri ...
is HNO3, and nitrous acid, HNO2. If there are more than two oxyacids having the same element as the central atom, then, in some cases, acids are distinguished by adding the prefix ''per-'' or ''hypo-'' to their names. The prefix ''per-'', however, is used only when the central atom is a
halogen The halogens () are a group in the periodic table consisting of five or six chemically related elements: fluorine (F), chlorine (Cl), bromine (Br), iodine (I), astatine (At), and tennessine (Ts). In the modern IUPAC nomenclature, this group is ...
or a
group 7 element Group 7, numbered by International Union of Pure and Applied Chemistry, IUPAC nomenclature, is a group of Chemical element, elements in the periodic table. They are manganese (Mn), technetium (Tc), rhenium (Re), and bohrium (Bh). All known elemen ...
. For example,
chlorine Chlorine is a chemical element with the Symbol (chemistry), symbol Cl and atomic number 17. The second-lightest of the halogens, it appears between fluorine and bromine in the periodic table and its properties are mostly intermediate betwee ...
has the four following oxyacids: * hypochlorous acid HClO * chlorous acid HClO2 *
chloric acid Chloric acid, H Cl O3, is an oxoacid of chlorine, and the formal precursor of chlorate salts. It is a strong acid ( p''K''a ≈ −2.7 (''***note: pKa not in agreement with properties in chem box at right'')) and oxidizing agent. Properties Chlo ...
HClO3 *
perchloric acid Perchloric acid is a mineral acid with the formula H Cl O4. Usually found as an aqueous solution, this colorless compound is a stronger acid than sulfuric acid, nitric acid and hydrochloric acid. It is a powerful oxidizer when hot, but aqueous sol ...
HClO4 The suffix ''-ite'' occurs in names of anions and salts derived from acids whose names end to the suffix ''-ous''. On the other hand, the suffix ''-ate'' occurs in names of anions and salts derived from acids whose names end to the suffix ''-ic''. Prefixes ''hypo-'' and ''per-'' occur in the name of anions and salts; for example the ion is called ''perchlorate''. In a few cases, the prefixes ''ortho-'' and ''para-'' occur in names of some oxyacids and their derivative anions. In such cases, the ''para-'' acid is what can be thought as remaining of the ''ortho-'' acid if a
water Water (chemical formula ) is an inorganic, transparent, tasteless, odorless, and nearly colorless chemical substance, which is the main constituent of Earth's hydrosphere and the fluids of all known living organisms (in which it acts as a ...
molecule is separated from the ''ortho-'' acid molecule. For example, phosphoric acid, H3PO4, has sometimes been called ''orthophosphoric acid'', in order to distinguish it from
metaphosphoric acid A phosphoric acid, in the general sense, is a phosphorus oxoacid in which each phosphorus (P) atom is in the oxidation state +5, and is bonded to four oxygen (O) atoms, one of them through a double bond, arranged as the corners of a tetrahedron. ...
, HPO3. However, according to
IUPAC The International Union of Pure and Applied Chemistry (IUPAC ) is an international federation of National Adhering Organizations working for the advancement of the chemical sciences, especially by developing nomenclature and terminology. It is ...
's current rules, the prefix ''ortho-'' should only be used in names of
orthotelluric acid Telluric acid is a chemical compound with the formula , often written as . It is a white crystalline solid made up of octahedral molecules which persist in aqueous solution. In the solid state, there are two forms, rhombohedral and monoclinic, a ...
and orthoperiodic acid, and their corresponding anions and salts.Red Book 2005, p. 132, note a


Examples

In the following table, the formula and the name of the anion refer to what remains of the acid when it loses ''all'' its hydrogen atoms as protons. Many of these acids, however, are
polyprotic In computer science, ACID ( atomicity, consistency, isolation, durability) is a set of properties of database transactions intended to guarantee data validity despite errors, power failures, and other mishaps. In the context of databases, a sequ ...
, and in such cases, there also exists one or more intermediate anions. In name of such anions, the prefix ''hydrogen-'' (in older nomenclature ''bi-'') is added, with
numeral prefix Numeral or number prefixes are prefixes derived from Numeral (linguistics), numerals or occasionally other numbers. In English and many other languages, they are used to coin numerous series of words. For example: * unicycle, bicycle, tricycle (1 ...
es if needed. For example, is the sulfate anion, and , the hydrogensulfate (or bisulfate) anion. Similarly, is
phosphate In chemistry, a phosphate is an anion, salt, functional group or ester derived from a phosphoric acid. It most commonly means orthophosphate, a derivative of orthophosphoric acid . The phosphate or orthophosphate ion is derived from phospho ...
, is hydrogenphosphate, and is dihydrogenphosphate.


Sources

* * *


See also

*
Weak acid Acid strength is the tendency of an acid, symbolised by the chemical formula HA, to dissociate into a hydron (chemistry), proton, H+, and an anion, A-. The Dissociation (chemistry), dissociation of a strong acid in solution is effectively comple ...
*
Hypohalous acid A hypohalous acid is an oxyacid consisting of a hydroxyl group single-bonded to any halogen. Examples include hypofluorous acid, hypochlorous acid, hypobromous acid, and hypoiodous acid. The conjugate base is a hypohalite. They can be formed by re ...
* Sulfur oxoacid


References

{{Reflist


External links


IUPAC definition of "oxoacid"
(from the ''Gold Book'') Acids Oxoacids