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Ozonide is the polyatomic anion . Cyclic organic compounds formed by the addition of
ozone Ozone () (or trioxygen) is an Inorganic compound, inorganic molecule with the chemical formula . It is a pale blue gas with a distinctively pungent smell. It is an allotrope of oxygen that is much less stable than the diatomic allotrope , break ...
() to an
alkene In organic chemistry, an alkene, or olefin, is a hydrocarbon containing a carbon–carbon double bond. The double bond may be internal or at the terminal position. Terminal alkenes are also known as Alpha-olefin, α-olefins. The Internationa ...
are also called ozonides.


Ionic ozonides

Inorganic ozonides are dark red salts. The anion has the bent shape of the ozone molecule. Inorganic ozonides are formed by burning
potassium Potassium is a chemical element; it has Symbol (chemistry), symbol K (from Neo-Latin ) and atomic number19. It is a silvery white metal that is soft enough to easily cut with a knife. Potassium metal reacts rapidly with atmospheric oxygen to ...
,
rubidium Rubidium is a chemical element; it has Symbol (chemistry), symbol Rb and atomic number 37. It is a very soft, whitish-grey solid in the alkali metal group, similar to potassium and caesium. Rubidium is the first alkali metal in the group to have ...
, or
caesium Caesium (IUPAC spelling; also spelled cesium in American English) is a chemical element; it has Symbol (chemistry), symbol Cs and atomic number 55. It is a soft, silvery-golden alkali metal with a melting point of , which makes it one of only f ...
in ozone, or by treating the
alkali metal The alkali metals consist of the chemical elements lithium (Li), sodium (Na), potassium (K),The symbols Na and K for sodium and potassium are derived from their Latin names, ''natrium'' and ''kalium''; these are still the origins of the names ...
hydroxide with ozone; this yields potassium ozonide, rubidium ozonide, and caesium ozonide respectively. They are very sensitive explosives that have to be handled at low temperatures in an
inert gas An inert gas is a gas that does not readily undergo chemical reactions with other chemical substances and therefore does not readily form chemical compounds. Though inert gases have a variety of applications, they are generally used to prevent u ...
atmosphere. Lithium and sodium ozonide are extremely labile and must be prepared by low-temperature ion exchange starting from . Sodium ozonide, , which is prone to decomposition into NaOH and , was previously thought to be impossible to obtain in pure form. However, with the help of
cryptand In chemistry, cryptands are a family of synthetic, bicyclic and polycyclic, multidentate ligands for a variety of cations. The Nobel Prize for Chemistry in 1987 was given to Donald J. Cram, Jean-Marie Lehn, and Charles J. Pedersen for ...
s and
methylamine Methylamine, also known as methanamine, is an organic compound with a formula of . This colorless gas is a derivative of ammonia, but with one hydrogen atom being replaced by a methyl group. It is the simplest primary amine. Methylamine is sold ...
, pure sodium ozonide may be obtained as red crystals isostructural to . Ionic ozonides are being investigated as sources of
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), group in the periodic table, a highly reactivity (chemistry), reactive nonmetal (chemistry), non ...
in chemical oxygen generators. Tetramethylammonium ozonide, which can be made by a metathesis reaction with caesium ozonide in liquid ammonia, is stable up to : : Alkaline earth metal ozonide compounds have also become known. For instance, magnesium ozonide complexes have been isolated in a low-temperature
argon Argon is a chemical element; it has symbol Ar and atomic number 18. It is in group 18 of the periodic table and is a noble gas. Argon is the third most abundant gas in Earth's atmosphere, at 0.934% (9340 ppmv). It is more than twice as abu ...
matrix.


Covalent singly bonded structures

Phosphite ozonides, , are used in the production of
singlet oxygen Singlet oxygen, systematically named dioxygen(singlet) and dioxidene, is a gaseous inorganic chemistry, inorganic chemical with the formula O=O (also written as or ), which is in a quantum state where all electrons are Radical (chemistry), spin p ...
. They are made by ozonizing a phosphite ester in dichloromethane at low temperatures, and decompose to yield singlet oxygen and a phosphate ester: : :


Molozonides

Molozonides are formed by the addition reaction between ozone and
alkene In organic chemistry, an alkene, or olefin, is a hydrocarbon containing a carbon–carbon double bond. The double bond may be internal or at the terminal position. Terminal alkenes are also known as Alpha-olefin, α-olefins. The Internationa ...
s. They are rarely isolated during the course of the
ozonolysis In organic chemistry, ozonolysis is an organic reaction where the Saturated and unsaturated compounds, unsaturated bonds are Bond cleavage, cleaved with ozone (). Multiple carbon–carbon bond are replaced by carbonyl () groups, such as aldehydes ...
reaction sequence. Molozonides are unstable and rapidly convert to the trioxolane ring structure with a five-membered C–O–O–C–O ring.Ozonolysis mechanism
on Organic Chemistry Portal site They usually appear in the form of foul-smelling oily liquids, and rapidly decompose in the presence of water to
carbonyl In organic chemistry, a carbonyl group is a functional group with the formula , composed of a carbon atom double bond, double-bonded to an oxygen atom, and it is divalent at the C atom. It is common to several classes of organic compounds (such a ...
compounds:
aldehyde In organic chemistry, an aldehyde () (lat. ''al''cohol ''dehyd''rogenatum, dehydrogenated alcohol) is an organic compound containing a functional group with the structure . The functional group itself (without the "R" side chain) can be referred ...
s,
ketone In organic chemistry, a ketone is an organic compound with the structure , where R and R' can be a variety of carbon-containing substituents. Ketones contain a carbonyl group (a carbon-oxygen double bond C=O). The simplest ketone is acetone ( ...
s,
peroxide In chemistry, peroxides are a group of Chemical compound, compounds with the structure , where the R's represent a radical (a portion of a complete molecule; not necessarily a free radical) and O's are single oxygen atoms. Oxygen atoms are joined ...
s. :


See also

*
Ozonolysis In organic chemistry, ozonolysis is an organic reaction where the Saturated and unsaturated compounds, unsaturated bonds are Bond cleavage, cleaved with ozone (). Multiple carbon–carbon bond are replaced by carbonyl () groups, such as aldehydes ...
* Ozone cracking *
Superoxide In chemistry, a superoxide is a compound that contains the superoxide ion, which has the chemical formula . The systematic name of the anion is dioxide(1−). The reactive oxygen ion superoxide is particularly important as the product of t ...
, *
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 st ...
, *
Dioxygenyl The dioxygenyl ion, , has been studied in both the gas phase and in salts with anions that cannot be oxidized. The first synthesis was []. Rather than the triple bond of , the bond order is considered to be . Relative to most molecules, this ioni ...
,


References


External links


Matrix reactions of alkali metal atoms with ozone: Infrared spectra of the alkali metal ozonide molecules
{{oxygen compounds Ozonides Free radicals Explosive chemicals