Oxyacid

Acid that contains oxygen

Not to be confused with keto acids, also known as oxocarboxylic acids, which are a type of oxoacid.

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An oxyacid, oxoacid, or ternary acid is an acid that contains oxygen. Specifically, it is a compound that contains hydrogen, oxygen, and at least one other element, with at least one hydrogen atom bonded to oxygen that can dissociate to produce the H+ cation and the anion of the acid.[1]

## Description

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Under Lavoisier's original theory, all acids contained oxygen, which was named from Ancient Greek: ὀξύς + -γενής, romanized: oxys + -genes, lit. 'acid, sharp + creator'. It was later discovered that some acids, notably hydrochloric acid, 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 oligomers (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 tautomeric 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 acids are created by replacing =O with =NR in an oxyacid.[2]

## Properties

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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, such a molecule can be dissociated into ions in two distinct ways:

* X−O−H ⇌ (X−O)− \+ H+
* X−O−H ⇌ X+ \+ OH−[3]

If the central atom X is strongly electronegative, then it strongly attracts the electrons 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, that is, a hydrogen ion. For example, nitrogen, sulfur and chlorine are strongly electronegative elements, and therefore nitric acid, sulfuric acid, and perchloric acid, are strong acids. The acidity of oxoacids is also affected by the resonance stabilization of their conjugate bases. Double-bonded oxygen is electron withdrawing by resonance, so the negative charge of a deprotonated hydroxyl group can be distributed to other oxygen atoms. Both acetic acid and methanol contain C-O-H groups that can act as acids, but acetic acid is a far stronger acid because its conjugate base, acetate, can distribute its negative charge over two oxygen atoms. In contrast, the conjugate acid of methanol has the negative charge localized on oxygen, so it is a far stronger base than acetate, making acetic acid the stronger acid.

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 hydroxide. Examples of such compounds are sodium hydroxide NaOH and calcium hydroxide Ca(OH)2.[3] 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, water, is 14.0, while that of sodium amide, ammonia, is closer to 40, making sodium hydroxide a much weaker base than sodium amide.[4][3]

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 water, aliphatic alcohols, such as ethanol, and aluminum hydroxide.[3]

Inorganic oxyacids typically have a chemical formula of type HmXOn, where X is an atom functioning as a central atom, whereas parameters m and n depend on the oxidation state of the element X. In most cases, the element X is a nonmetal, but some metals, for example chromium and manganese, can form oxyacids when occurring at their highest oxidation states.[3]

When oxyacids are heated, many of them dissociate to water and the anhydride of the acid. In most cases, such anhydrides are oxides of nonmetals. For example, carbon dioxide, CO2, is the anhydride of carbonic acid, H2CO3, and sulfur trioxide, SO3, is the anhydride of sulfuric acid, H2SO4. These anhydrides react quickly with water and form those oxyacids again.[5]

Many organic acids, like carboxylic acids and phenols, are oxyacids.[3] Their molecular structure, however, is much more complicated than that of inorganic oxyacids.

Most of the commonly encountered acids are oxyacids.[3] Indeed, in the 18th century, Lavoisier assumed that all acids contain oxygen and that oxygen causes their acidity. Because of this, he gave to this element its name, oxygenium, derived from Greek and meaning acid-maker, which is still, in a more or less modified form, used in most languages.[6] Later, however, Humphry Davy 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, HCl.[7] Such acids which do not contain oxygen are nowadays known as hydroacids.

## Names of inorganic oxyacids

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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, nitric acid and phosphoric acid.

This practice is fully well-established, and IUPAC has accepted such names. In light of the current chemical nomenclature, 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.[8]

IUPAC, however, recommends against calling future compounds not yet discovered with a name ending with the word acid.[8] Indeed, acids can be called with names formed by adding the word hydrogen in front of the corresponding anion; for example, sulfuric acid could just as well be called hydrogen sulfate (or dihydrogen sulfate).[9] 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−),[10] 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 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 is H2SO4, and sulfurous acid, H2SO3. Analogously, nitric acid 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 or a group 7 element.[9] For example, chlorine has the four following oxyacids:

* hypochlorous acid HClO
* chlorous acid HClO2
* chloric acid HClO3
* perchloric acid HClO4

Some elemental atoms can exist in a high enough oxidation state that they can hold one more double-bonded oxygen atom than the perhalic acids do. In that case, any acids regarding such element are given the prefix hyper-. Currently, the only known acid with this prefix is hyperruthenic acid, H2RuO5.

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 ClO−
4 is called perchlorate.[9]

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 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, HPO3.[9] However, according to IUPAC's current rules, the prefix ortho- should only be used in names of orthotelluric acid and orthoperiodic acid, and their corresponding anions and salts.[11]

### Examples

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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, 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 prefixes if needed. For example, SO2−
4 is the sulfate anion, and HSO−
4, the hydrogensulfate (or bisulfate) anion. Similarly, PO3−
4 is phosphate, HPO2−
4 is hydrogenphosphate, and H
2PO−
4 is dihydrogenphosphate.

Oxyacids and their corresponding anions  Element group | Element (central atom) | Oxidation state | Acid formula | Acid name[9][10] | Anion formula | Anion name

|
|
|
|
|
|

6 | Chromium | +6 | H
2CrO
4 | Chromic acid | CrO2−
4 | Chromate

2Cr

7 | Dichromic acid | Cr
2O2−
7 | Dichromate
7 | Manganese | +7 | HMnO
4 | Permanganic acid | MnO−
4 | Permanganate
+6 | H
2MnO
4 | Manganic acid | MnO2−
4 | Manganate
Technetium | +7 | HTcO
4 | Pertechnetic acid | TcO−
4 | Pertechnetate
+6 | H
2TcO
4 | Technetic acid | TcO2−
4 | Technetate
Rhenium | +7 | HReO
4 | Perrhenic acid | ReO−
4 | Perrhenate
+6 | H
2ReO
4 | Tetraoxorhenic(VI) acid | ReO2−
4 | Rhenate(VI)
+5 | HReO
3 | Trioxorhenic(V) acid | ReO−
3 | Trioxorhenate(V)

3ReO
4 | Tetraoxorhenic(V) acid | ReO3−
4 | Tetraoxorhenate(V)

4Re

7 | Heptaoxodirhenic(V) acid | Re
2O4−
7 | Dirhenate(V)
8 | Iron | +6  | H2FeO4 | Ferric acid  | FeO42– | Ferrate
Ruthenium | +6  | H2RuO4 | Ruthenic acid  | RuO42– | Ruthenate
+7  | HRuO4 | Perruthenic acid  | RuO4– | Perruthenate (note difference in usage compared to osmium)
+8  | H2RuO5 | Hyperruthenic acid  | HRuO5– | Hyperruthenate[12]
Osmium | +6  | H6OsO6 | Osmic acid  | H4OsO62– | Osmate
+8  | H4OsO6 | Perosmic acid  | H2OsO62– | Perosmate (note difference in usage compared to ruthenium)
13 | Boron | +3 | H
3BO
3 | Boric acid
(formerly orthoboric acid)[11] | BO3−
3 | Borate
(formerly orthoborate)
(HBO

n | Metaboric acid | BO−
2 | Metaborate
14 | Carbon | +4 | H
2CO
3 | Carbonic acid | CO2−
3 | Carbonate
Silicon | +4 | H
4SiO
4 | Silicic acid
(formerly orthosilicic acid)[11] | SiO4−
4 | Silicate (formerly orthosilicate)

2SiO
3 | Metasilicic acid | SiO2−
3 | Metasilicate
14, 15 | Carbon, nitrogen | +4, −3 | HOCN | Cyanic acid | OCN−
| Cyanate
15 | Nitrogen | +5 | HNO
3 | Nitric acid | NO−
3 | Nitrate
HNO
4 | Peroxynitric acid | NO−
4 | Peroxynitrate

3NO
4 | Orthonitric acid | NO3−
4 | Orthonitrate
+3 | HNO
2 | Nitrous acid | NO−
2 | Nitrite
HOONO | Peroxynitrous acid | OONO−
| Peroxynitrite
+2 | H
2NO
2 | Nitroxylic acid | NO2−
2 | Nitroxylate
+1 | H

2 | Hyponitrous acid | N
2O2−
2 | Hyponitrite
Phosphorus | +5 | H
3PO
4 | Phosphoric acid
(formerly orthophosphoric acid)[11] | PO3−
4 | Phosphate
(orthophosphate)
HPO
3 | Metaphosphoric acid | PO−
3 | Metaphosphate

7 | Pyrophosphoric acid
(diphosphoric acid) | P
2O4−
7 | Pyrophosphate
(diphosphate)

3PO
5 | Peroxomonophosphoric acid | PO3−
3 | Peroxomonophosphate
+5, +3 | (HO)
2POPO(OH)
2 | Diphosphoric(III,V) acid | O
2POPOO2−
2 | Diphosphate(III,V)
+4 | (HO)
2OPPO(OH)
2 | Hypophosphoric acid
(diphosphoric(IV) acid) | O
2OPPOO4−
2 | Hypophosphate
(diphosphate(IV))
+3 | H
2PHO
3 | Phosphonic acid | PHO2−
3 | Phosphonate

5 | Diphosphonic acid | P

2O5−
3 | Diphosphonate
+1 | HPH

2 | Phosphinic acid (hypophosphorous acid) | PH
2O−
2 | Phosphinate (hypophosphite)
Arsenic | +5 | H
3AsO
4 | Arsenic acid | AsO3−
4 | Arsenate
+3 | H
3AsO
3 | Arsenous acid | AsO3−
3 | Arsenite
16 | Sulfur | +6 | H
2SO
4 | Sulfuric acid | SO2−
4 | Sulfate

7 | Disulfuric acid | S
2O2−
7 | Disulfate

2SO
5 | Peroxomonosulfuric acid | SO2−
5 | Peroxomonosulfate

8 | Peroxodisulfuric acid | S
2O2−
8 | Peroxodisulfate
+5 | H

6 | Dithionic acid | S
2O2−
6 | Dithionate
+5, 0 | H

6 | Polythionic acids
(x = 3, 4...) | S
xO2−
6 | Polythionates
+4 | H
2SO
3 | Sulfurous acid | SO2−
3 | Sulfite

5 | Disulfurous acid | S
2O2−
5 | Disulfite
+4, 0 | H

3 | Thiosulfuric acid | S
2O2−
3 | Thiosulfate
+3 | H

4 | Dithionous acid | S
2O2−
4 | Dithionite
+3, −1 | HOSOSH | Thiosulfurous acid | OSOS2−
| Thiosulfite
+2 | H
2SO
2 | Sulfoxylic acid (hyposulfurous acid) | SO2−
2 | Sulfoxylate (hyposulfite)
+1 | HOSSOH | Dihydroxydisulfane | OSSO2−
| Disulfanediolate[13]
0 | HSOH | Sulfenic acid | HSO−
| Sulfinite
Selenium | +6 | H
2SeO
4 | Selenic acid | SeO2−
4 | Selenate
+4 | H
2SeO
3 | Selenous acid | SeO2−
3 | Selenite
Tellurium | +6 | H
2TeO
4 | Telluric acid | TeO2−
4 | Tellurate

6TeO
6 | Orthotelluric acid | TeO6−
6 | Orthotellurate
+4 | H
2TeO
3 | Tellurous acid | TeO2−
3 | Tellurite
17 | Chlorine | +7 | HClO
4 | Perchloric acid | ClO−
4 | Perchlorate
+5 | HClO
3 | Chloric acid | ClO−
3 | Chlorate
+3 | HClO
2 | Chlorous acid | ClO−
2 | Chlorite
+1 | HClO | Hypochlorous acid | ClO−
| Hypochlorite
Bromine | +7 | HBrO
4 | Perbromic acid | BrO−
4 | Perbromate
+5 | HBrO
3 | Bromic acid | BrO−
3 | Bromate
+3 | HBrO
2 | Bromous acid | BrO−
2 | Bromite
+1 | HBrO | Hypobromous acid | BrO−
| Hypobromite
Iodine | +7 | HIO
4 | Periodic acid | IO−
4 | Periodate

5IO
6 | Orthoperiodic acid | IO5−
6 | Orthoperiodate
+5 | HIO
3 | Iodic acid | IO−
3 | Iodate
+1 | HIO | Hypoiodous acid | IO−
| Hypoiodite
18 | Xenon | +6  | H2XeO4 | Xenic acid | HXeO4– | Hydrogenxenate (dibasic xenate is unknown)
+8  | H4XeO6 | Perxenic acid | XeO64– | Perxenate

## Sources

[edit]

* Kivinen, Antti; Mäkitie, Osmo (1988). Kemia (in Finnish). Helsinki, Finland: Otava. ISBN 951-1-10136-6.
* Nomenclature of Inorganic Compounds, IUPAC Recommendations 2005 (Red Book 2005). International Union of Pure and Applied Chemistry. 2005. ISBN 0-85404-438-8.[dead link]
* Otavan suuri ensyklopedia, volume 2 (Cid-Harvey) (in Finnish). Helsinki, Finland: Otava. 1977. ISBN 951-1-04170-3.

## See also

[edit]

* Weak acid
* Hypohalous acid
* Sulfur oxoacid
* Sulphuric acid

## References

[edit]

1. ^ Chemistry, International Union of Pure and Applied. IUPAC Compendium of Chemical Terminology. IUPAC. doi:10.1351/goldbook.O04374.
2. ^ Chemistry, International Union of Pure and Applied. IUPAC Compendium of Chemical Terminology. IUPAC. doi:10.1351/goldbook.I02949.
3. ^ a b c d e f g Kivinen, Mäkitie: Kemia, p. 202-203, chapter=Happihapot
4. ^ Meister, Erich C.; Willeke, Martin; Angst, Werner; Togni, Antonio; Walde, Peter (2014). "Confusing Quantitative Descriptions of BrønstedLowry AcidBase Equilibria in Chemistry Textbooks – A Critical Review and Clarifications for Chemical Educators". Helvetica Chimica Acta. 97 (1): 1–31\. doi:10.1002/hlca.201300321. ISSN 1522-2675.
5. ^ "Hapot". Otavan iso Fokus, Part 2 (El-Io). Otava. 1973. p. 990\. ISBN 951-1-00272-4.
6. ^ Otavan suuri Ensyklopedia, s. 1606, art. Happi
7. ^ Otavan suuri Ensyklopedia, s. 1605, art. Hapot ja emäxet
8. ^ a b Red Book 2005, s. 124, chapter IR-8: Inorganic Acids and Derivatives
9. ^ a b c d e Kivinen, Mäkitie: Kemia, p. 459-461, chapter Kemian nimistö: Hapot
10. ^ a b Red Book 2005, p. 129-132, table IR-8-1
11. ^ a b c d Red Book 2005, p. 132, note a
12. ^ Encyclopedia of electrochemical power sources. Garche, Jürgen., Dyer, Chris K. Amsterdam: Academic Press. 2009. p. 854\. ISBN 978-0444527455. OCLC 656362152.`{{cite book}}`: CS1 maint: others (link)
13. ^ "CSID:7827570 | O2S2 | ChemSpider". www.chemspider.com. Retrieved 2023-01-01.

## External links

[edit]

* IUPAC definition of "oxoacid" (from the Gold Book)

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Carbon–carbon lyases (EC 4.1)

4.1.1: Carboxy-lyases|

* Acetoacetate decarboxylase
* Adenosylmethionine decarboxylase
* Arginine decarboxylase
* Aromatic L-amino acid decarboxylase
* Glutamate decarboxylase
* Histidine decarboxylase
* Lysine decarboxylase
* Malonyl-CoA decarboxylase
* Ornithine decarboxylase
* Oxaloacetate decarboxylase
* Phosphoenolpyruvate carboxykinase
* Phosphoenolpyruvate carboxylase
* Phosphoribosylaminoimidazole carboxylase
* Pyrophosphomevalonate decarboxylase
* Pyruvate decarboxylase
* RuBisCO
* Uridine monophosphate synthetase/Orotidine 5'-phosphate decarboxylase
* Uroporphyrinogen III decarboxylase

4.1.2: Aldehyde-lyases|

* Fructose-bisphosphate aldolase
* Aldolase A
* Aldolase B
* Aldolase C
* 2-hydroxyphytanoyl-CoA lyase
* Threonine aldolase

4.1.3: Oxo-acid-lyases|

* Isocitrate lyase
* 3-hydroxy-3-methylglutaryl-CoA lyase

4.1.99: Other|

* Tryptophanase
* Photolyase
* CPD lyase
* Spore photoproduct lyase

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Carbon–oxygen lyases (EC 4.2) (primarily dehydratases)

4.2.1: Hydro-Lyases|

* Carbonic anhydrase
* Fumarase
* Aconitase
* Enolase
* Alpha
* Enolase 2
* Enoyl-CoA hydratase/3-Hydroxyacyl ACP dehydrase
* Methylglutaconyl-CoA hydratase
* Tryptophan synthase
* Cystathionine beta synthase
* Porphobilinogen synthase
* 3-Isopropylmalate dehydratase
* Urocanase
* Uroporphyrinogen III synthase
* Nitrile hydratase

4.2.2: Acting on polysaccharides|

* Hyaluronate lyase
* Pectin lyase

4.2.3: Acting on phosphates|

* Threonine synthase

4.2.99: Other|

* Carboxymethyloxysuccinate lyase
* Hydroperoxide lyase

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Carbon–nitrogen lyases (EC 4.3)

4.3.1: ammonia-lyases|

* Histidine ammonia-lyase
* Formiminotransferase cyclodeaminase
* Serine dehydratase
* Phenylalanine ammonia-lyase

4.3.2: amidine-lyases|

* Argininosuccinate lyase
* Adenylosuccinate lyase

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Carbon–sulfur lyases (EC 4.4)

4.4.1|

* Cystathionine gamma-lyase
* Cystathionine beta-lyase
* Leukotriene C4 synthase

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Carbon–halide lyases (EC 4.5)

4.5.1|

* Dichloromethane dehalogenase
* Halohydrin dehalogenase

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Phosphorus–oxygen lyases (EC 4.6)

4.6.1|

| Adenylate cyclase
(4.6.1.1)|

| intracellular|

* ADCY1
* ADCY2
* ADCY3
* ADCY4
* ADCY5
* ADCY6
* ADCY7
* ADCY8
* ADCY9
* ADCY10

|

extracellular|

* Extracellular adenylate cyclase

Guanylate cyclase
(4.6.1.2)|

| soluble guanylyl cyclase|

* GUCY1A2
* GUCY1A3
* GUCY1B2
* GUCY1B3

|

guanylate cyclase-coupled receptor|

* GUCY2C
* GUCY2D
* ANP (NPR1
* NPR2)

Other|

* Cytidylate cyclase
* 2-C-methyl-D-erythritol 2,4-cyclodiphosphate synthase
* Phosphatidylinositol diacylglycerol-lyase
* Glycosylphosphatidylinositol diacylglycerol-lyase
* FAD-AMP lyase (cyclizing)

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