Peroxide

Chemical compounds with the structure R–O–O–R'

For other uses, see Peroxide (disambiguation).

In chemistry, peroxides are a group of compounds with the structure R−O−O−R, where the R's represent a radical (a portion of a complete molecule; not necessarily a free radical[1]) and O's are single oxygen atoms.[2][3] Oxygen atoms are joined to each other and to adjacent elements through single covalent bonds, denoted by dashes or lines. The O−O group in a peroxide is often called the peroxide group, though some nomenclature discrepancies exist. This linkage is recognized as a common polyatomic ion, and exists in many molecules.

## General structure

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The characteristic structure of any regular peroxide is the oxygen–oxygen covalent single bond, which connects the two main atoms together. In the event that the molecule has no chemical substituents, the peroxide group will have a [−2] net charge. Each oxygen atom has a charge of negative one, as 5 of its valence electrons remain in the outermost orbital shell whilst one is occupied in the covalent bond. Because of the nature of the covalent bond, this arrangement results in each atom having the equivalent of 7 valence electrons, reducing the oxygens and giving them a negative charge. This charge is affected by the addition of other elements, with the properties and structure changing depending on the added group(s).

## Common forms

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Types of peroxides, from top to bottom: peroxide ion, organic peroxide, organic hydroperoxide, peracid. The peroxide group is marked in blue. R, R1 and R2 mark hydrocarbon moieties.

The most common peroxide is hydrogen peroxide (H2O2), colloquially known simply as "peroxide". It is marketed as solutions in water at various concentrations. Many organic peroxides are known as well.

In addition to hydrogen peroxide, some other major classes of peroxides are:

* Peroxy acids, the peroxy derivatives of many familiar acids, examples being peroxymonosulfuric acid and peracetic acid, and their salts, one example of which is potassium peroxydisulfate.
* Main group peroxides, compounds with the linkage E−O−O−E (E = main group element).

Structure and dimensions of H2O2 in gas phase.

* Metal peroxides, examples being barium peroxide (BaO2), sodium peroxide (Na2O2) and zinc peroxide (ZnO2).
* Organic peroxides, compounds with the linkage C−O−O−C or C−O−O−H. One example is tert-butylhydroperoxide.

## Nomenclature

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The linkage between the oxygen molecules is known as a peroxy group (sometimes called peroxo group, peroxyl group, of peroxy linkage). The nomenclature of the peroxy group is somewhat variable,[4] and exists as an exception to the rules of naming polyatomic ions. This is because, when it was discovered, it was believed to be monatomic.[5] The term was introduced by Thomas Thomson in 1804 for a compound combined with as much oxygen as possible,[6] or the oxide with the greatest quantity of oxygen.[7]

## References

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1. ^ "Illustrated Glossary of Organic Chemistry". UCLA. Retrieved June 19, 2024.
2. ^ Greenwood, Norman N.; Earnshaw, Alan (1997). Chemistry of the Elements (2nd ed.). Butterworth-Heinemann. ISBN 978-0-08-037941-8.
3. ^ Smith, Michael B.; March, Jerry (2007), Advanced Organic Chemistry: Reactions, Mechanisms, and Structure (6th ed.), New York: Wiley-Interscience, ISBN 978-0-471-72091-1
4. ^ IUPAC, Compendium of Chemical Terminology, 2nd ed. (the "Gold Book") (1997). Online corrected version: (2006-) "peroxides". doi:10.1351/goldbook.P04510
5. ^ "Nomenclature". Purdue Division of Chemical Education. 2004. Retrieved March 25, 2024.
6. ^ Thomson, Thomas (1804). "4". A System of Chemistry. Vol. 1 (2nd ed.). Edinburgh: Bell and Bradfute. pp. division 1, page 103 - via Google books.
7. ^ Harper, Douglas. "Peroxide". Online Etymology Dictionary.

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Functional groups

Hydrocarbons
(only C and H)|

* Alkyl
* Methyl
* Ethyl
* Propyl
* Cyclopropyl
* Butyl
* Pentyl
* Methylene
* Bridge
* Methine
* Alkene
* Vinyl
* Allyl
* 1-Propenyl
* Crotyl
* Allene
* Cumulene
* Aryl
* Phenyl
* Benzyl
* Alkyne
* Carbene

Only carbon,
hydrogen,
and oxygen
(only C, H and O)|

| R-O-R|

* Acetal
* Alcohol
* Alkoxy
* Methoxy
* Ether
* Enol ether
* Epoxide
* Peroxy
* Hydroperoxy
* Dioxiranes
* Ethylenedioxy
* Methylenedioxy

|

carbonyl|

* Acyl
* Acetyl
* Acryloyl
* Benzoyl
* Aldehyde
* Ketene
* Ketone
* Ynone
* Reductone

carboxy|

* Carboxyl
* Acetoxy
* Anhydride
* Ester
* Orthoester

Only one
element,
not being
carbon,
hydrogen,
or oxygen
(one element,
not C, H or O)|

| Nitrogen|

* Amine
* Enamine
* Ammonium
* Hydrazo
* Nitrene
* Imine
* Oxime
* Hydrazone
* Azo
* Amide
* Imidate
* Amidine
* Carbamate
* Imide
* Nitrile
* Isonitrile
* Cyanate
* Isocyanate
* Nitrate
* Nitrite
* Nitro
* Nitroso
* NONOate

|

Silicon|

* Silane
* Hydrosilane
* Chlorosilane
* Silene
* Silanol
* Siloxide
* Siloxane
* Silanone
* Silether
* Silole
* Silatrane
* Silicate

Phosphorus|

* Phosphate
* Phosphodiester
* Phosphonate
* Phosphite
* Phosphonous
* Phosphinate
* Phosphine oxide
* Phosphine
* Phosphonium
* Phosphaalkene
* Phosphaalkyne
* Phosphaallene

Sulfur|

* Thiol
* Thioether
* Sulfonium
* Thia-crown ether
* Persulfide
* Disulfide
* Sulfenic acid
* Thiosulfinate
* Sulfoxide
* Thiosulfonate
* Sulfinic acid
* Sulfone
* Sulfonic acid
* Thioketone
* Thial
* Thioester
* Thionoester
* Thioxanthate
* Xanthate

Boron|

* Boronic acid
* Borinic acid

Selenium|

* Selenol
* Selenonic acid
* Seleninic acid
* Selenenic acid
* Selone
* Selenoether

Tellurium|

* Tellurol
* Telluroketone
* telluroether

Polonium|

* Polonol
* Polonoether

Halo|

* Haloalkane
* Fluoroethyl
* Trifluoromethyl
* Trichloromethyl
* Trifluoromethoxy
* Hypervalent iodine
* Vinyl halide
* Iodide
* Acyl halide
* Chloride
* Perchlorate

Other|

* Isothiocyanate
* Phosphoramides
* Sulfenyl chloride
* Sulfonamide
* Thiocyanate
* Sulfinylamines

See also
chemical classification
chemical nomenclature

inorganic
organic

Authority control databases: National |

* Germany
* United States
* Japan
* Israel

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