Ozonide is the
polyatomic anion .
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 lo ...
() 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 atmosp ...
,
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 hig ...
, 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 ...
in ozone, or by treating the
alkali metal 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 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, , which is prone to decomposition into
NaOH and
, was previously thought to be impossible to obtain in pure form. However, with the help of
cryptands and
methylamine, pure
sodium ozonide 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 we ...
in
chemical oxygen generators.
Tetramethylammonium ozonide, which can be made by a
metathesis reaction with caesium ozonide in
liquid ammonia, is stable up to :
:
CsO3 + CH3)4NO2] -> CsO2 + CH3)4NO3]
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 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 a ...
matrix.
Covalent singly bonded structures
Phosphite ozonides, , are used in the production of
singlet oxygen. They are made by ozonizing a
phosphite ester in
dichloromethane at low temperatures, and decompose to yield singlet oxygen and a
phosphate ester:
#
(RO)3P + O3 -> (RO)3PO3
#
(RO)3PO3 -> (RO)3PO + ^O2
Molozonides
Molozonides 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 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 containin ...
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 group ...
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 ...
s.
See also
* Ozonolysis
* Ozone cracking
* Superoxide,
* Oxide,
* 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