Ozonide is the
polyatomic anion
A polyatomic ion, also known as a molecular ion, is a covalent bonded set of two or more atoms, or of a metal complex, that can be considered to behave as a single unit and that has a net charge that is not zero. The term molecule may or may not ...
.
Cyclic organic compounds formed by the addition of
ozone
Ozone (), or trioxygen, is an 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 , breaking down in the lowe ...
() to an
alkene
In organic chemistry, an alkene is a hydrocarbon containing a carbon–carbon double bond.
Alkene is often used as synonym of olefin, that is, any hydrocarbon containing one or more double bonds.H. Stephen Stoker (2015): General, Organic, an ...
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 the chemical element with the symbol K (from Neo-Latin ''kalium'') and atomic number19. Potassium is a silvery-white metal that is soft enough to be cut with a knife with little force. Potassium metal reacts rapidly with atmosphe ...
,
rubidium
Rubidium is the chemical element with the 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 a density higher ...
, or
caesium
Caesium ( IUPAC spelling) (or cesium in American English) is a chemical element with the 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 five elemental metals that a ...
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
Potassium ozonide is an oxygen rich compound of potassium. It is an ozonide, meaning it contains the ozonide anion (O3−). In polarized light, it shows pleochroism. Hybrid functional calculations have predicted the compound is an insulator with ...
,
rubidium ozonide, and
caesium ozonide respectively. They are very sensitive explosives that have to be handled at low temperatures in an atmosphere consisting of 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. The noble gases often do not react with many substances and were historically referred to ...
. Lithium and sodium ozonide are extremely labile and must be prepared by low-temperature ion exchange starting from .
Sodium ozonide
Sodium ozonide (NaO3) is an oxygen-rich compound of sodium. As an ozonide, it contains the ozonide anion (O3−).
Some experiments report creating sodium ozonide by applying ozone to sodium hydroxide, but the substance was not pure, and the claim ...
, , which is prone to decomposition into
NaOH
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 t ...
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 their ...
s and
methylamine
Methylamine 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 as a solution in methanol, e ...
, pure
sodium ozonide
Sodium ozonide (NaO3) is an oxygen-rich compound of sodium. As an ozonide, it contains the ozonide anion (O3−).
Some experiments report creating sodium ozonide by applying ozone to sodium hydroxide, but the substance was not pure, and the claim ...
may be obtained as red crystals isostructural to
.
Ionic ozonides are being investigated as sources of
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 ...
in
chemical oxygen generator
A chemical oxygen generator is a device that releases oxygen via a chemical reaction. The oxygen source is usually an inorganic superoxide, chlorate, or perchlorate; ozonides are a promising group of oxygen sources. The generators are usually igni ...
s.
Tetramethylammonium
Tetramethylammonium (TMA) or (Me4N+) is the simplest quaternary ammonium cation, consisting of four methyl groups attached to a central nitrogen atom, and is isoelectronic with neopentane. It is positively charged and can only be isolated in asso ...
ozonide, which can be made by a
metathesis reaction with caesium ozonide in
liquid 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 wa ...
, is stable up to :
:
CsO3 + CH3)4NO2] -> CsO2 + CH3)4NO3]
Alkaline earth metal ozonide compounds have also become known. For instance,
magnesium ozonide
Magnesium ozonide is a compound with the formula Mg O3. Much like other ozonide
Ozonide is the polyatomic anion . Cyclic organic compounds formed by the addition of ozone () to an alkene are also called ozonides.
Ionic ozonides
Inorganic oz ...
complexes have been isolated in a low-temperature
argon
Argon is a chemical element with the 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 ...
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 chemical with the formula O=O (also written as or ), which is in a quantum state where all electrons are spin paired. It is kinetically unstable at ambie ...
. They are made by ozonizing a
phosphite ester
The general structure of a phosphite ester showing the lone pairs on the P
In organic chemistry, a phosphite ester or organophosphite usually refers to an organophosphorous compound with the formula P(OR)3. They can be considered as esters of ...
in
dichloromethane
Dichloromethane (DCM or methylene chloride, methylene bichloride) is an organochlorine compound with the formula . This colorless, volatile liquid with a chloroform-like, sweet odour is widely used as a solvent. Although it is not miscible with w ...
at low temperatures, and decompose to yield singlet oxygen and a
phosphate ester:
#
(RO)3P + O3 -> (RO)3PO3
#
(RO)3PO3 -> (RO)3PO + ^O2
Molozonides
Molozonide
A molozonide (or "molecular ozonide") is a 1,2,3-trioxolane, which can also be thought of a cyclic dialkyl trioxidane. Molozonides are formed by cycloaddition of ozone and an alkene during ozonolysis, as a transient intermediate which quickly rea ...
s are formed by the addition reaction between ozone and
alkene
In organic chemistry, an alkene is a hydrocarbon containing a carbon–carbon double bond.
Alkene is often used as synonym of olefin, that is, any hydrocarbon containing one or more double bonds.H. Stephen Stoker (2015): General, Organic, an ...
s. They are rarely isolated during the course of the
ozonolysis
In organic chemistry, ozonolysis is an organic reaction where the unsaturated bonds of alkenes (), alkynes (), or azo compounds () are cleaved with ozone (). Alkenes and alkynes form organic compounds in which the multiple carbon–carbon bond ...
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 composed of a carbon atom double-bonded to an oxygen atom: C=O. It is common to several classes of organic compounds, as part of many larger functional groups. A compound containing a ...
compounds: aldehyde
In organic chemistry, an aldehyde () is an organic compound containing a functional group with the structure . The functional group itself (without the "R" side chain) can be referred to as an aldehyde but can also be classified as a formyl grou ...
s, ketone
In organic chemistry, a ketone is a functional group with the structure R–C(=O)–R', where R and R' can be a variety of carbon-containing substituents. Ketones contain a carbonyl group –C(=O)– (which contains a carbon-oxygen double bon ...
s, peroxide
In chemistry, peroxides are a group of compounds with the structure , where R = any element. The group in a peroxide is called the peroxide group or peroxo group. The nomenclature is somewhat variable.
The most common peroxide is hydrogen p ...
s.
See also
* Ozonolysis
In organic chemistry, ozonolysis is an organic reaction where the unsaturated bonds of alkenes (), alkynes (), or azo compounds () are cleaved with ozone (). Alkenes and alkynes form organic compounds in which the multiple carbon–carbon bond ...
* Ozone cracking
Cracks can be formed in many different elastomers by ozone attack, and the characteristic form of attack of vulnerable rubbers is known as ozone cracking. The problem was formerly very common, especially in tires, but is now rarely seen in those ...
* 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 th ...
,
* 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 th ...
,
* Dioxygenyl,
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