Ozonide is the
polyatomic anionO−3.
Cyclic organic compounds formed by the addition of
ozone (O3) to an
alkene are also called ozonides.
Ionic ozonides
Inorganic ozonides[1] are dark red salts. The anion has the
bent shape of the ozone molecule.
Inorganic ozonides are formed by burning
potassium,
rubidium, or
caesium 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. Lithium and sodium ozonide are extremely labile and must be prepared by low-temperature ion exchange starting from CsO3.
Sodium ozonide, NaO3, which is prone to decomposition into
NaOH and
NaO2, was previously thought to be impossible to obtain in pure form.[2] However, with the help of
cryptands and
methylamine, pure
sodium ozonide may be obtained as red crystals isostructural to
NaNO2.[3]
Alkaline earth metal ozonide compounds have also become known. For instance,
magnesium ozonide complexes have been isolated in a low-temperature
argon matrix.[5]
Molozonides are formed by the addition reaction between ozone and
alkenes. 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.[8][9] They usually appear in the form of foul-smelling oily liquids, and rapidly decompose in the presence of water to
carbonyl compounds:
aldehydes,
ketones,
peroxides.
^Cotton, F. A.; Wilkinson, G. (1988). Advanced Inorganic Chemistry (5th ed.). p. 462.
^Korber, N.; Jansen, M. (1996). "Ionic Ozonides of Lithium and Sodium: Circumventive Synthesis by Cation Exchange in Liquid Ammonia and Complexation by Cryptands". Chemische Berichte. 129 (7): 773–777.
doi:
10.1002/cber.19961290707.
^Catherine E. Housecroft; Alan G. Sharpe (2008). "Chapter 16: The group 16 elements". Inorganic Chemistry, 3rd Edition. Pearson. p. 496.
ISBN978-0-13-175553-6.
^Wasserman HH, DeSimone RW, Chia KR, Banwell MG (2001). "Singlet Oxygen". Encyclopedia of Reagents for Organic Synthesis. e-EROS Encyclopedia of Reagents for Organic Synthesis. John Wiley & Sons.
doi:
10.1002/047084289X.rs035.
ISBN978-0471936237.
^Criegee, Rudolf (1975). "Mechanism of Ozonolysis". Angewandte Chemie International Edition in English. 14 (11): 745–752.
doi:
10.1002/anie.197507451.