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Ozonide

From Wikipedia, the free encyclopedia
Polyatomic ion (O3, charge –1), or cyclic compounds made from ozone and alkenes
Ozonide
Names
IUPAC name
Trioxidan-1-id-3-yl
Identifiers
3D model (JSmol)
ChEBI
ChemSpider
25183
  • InChI=1S/HO3/c1-3-2/h1H/p-1
    Key: WURFKUQACINBSI-UHFFFAOYSA-M
  • InChI=1/HO3/c1-3-2/h1H/p-1
    Key: WURFKUQACINBSI-REWHXWOFAH
  • [O-]O[O]
  • [O-][O+][O-]
Properties
O3
Molar mass47.997 g·mol−1
Except where otherwise noted, data are given for materials in theirstandard state (at 25 °C [77 °F], 100 kPa).
Chemical compound

Ozonide is thepolyatomic anionO3.Cyclic organic compounds formed by the addition ofozone (O3) to analkene are also called ozonides.

Ionic ozonides

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Inorganic ozonides[1] are dark red salts. The anion has thebent shape of the ozone molecule.

Inorganic ozonides are formed by burningpotassium,rubidium, orcaesium in ozone, or by treating thealkali metal hydroxide with ozone; this yieldspotassium ozonide,rubidium ozonide, andcaesium ozonide respectively. They are very sensitive explosives that have to be handled at low temperatures in aninert gas atmosphere. Lithium and sodium ozonide are extremely labile and must be prepared by low-temperature ion exchange starting fromCsO3.Sodium ozonide,NaO3, which is prone to decomposition intoNaOH andNaO2, was previously thought to be impossible to obtain in pure form.[2] However, with the help ofcryptands andmethylamine, puresodium ozonide may be obtained as red crystals isostructural toNaNO2.[3]

Ionic ozonides are being investigated[citation needed] as sources ofoxygen inchemical oxygen generators.Tetramethylammonium ozonide, which can be made by ametathesis reaction with caesium ozonide inliquid ammonia, is stable up to 348 K (75 °C):[4]

CsO3 + [(CH3)4N][O2] → CsO2 + [(CH3)4N][O3]

Alkaline earth metal ozonide compounds have also become known. For instance,magnesium ozonide complexes have been isolated in a low-temperatureargon matrix.[5]

Covalent singly bonded structures

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Phosphite ozonides,(RO)3PO3, are used in the production ofsinglet oxygen. They are made by ozonizing aphosphite ester indichloromethane at low temperatures, and decompose to yield singlet oxygen and aphosphate ester:[6][7]

(RO)3P + O3 → (RO)3PO3
(RO)3PO3 → (RO)3PO +1O2

Molozonides

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Molozonides are formed by the addition reaction between ozone andalkenes. They are rarely isolated during the course of theozonolysis reaction sequence. Molozonides are unstable and rapidly convert to thetrioxolane 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 tocarbonyl compounds:aldehydes,ketones,peroxides.

Formation of an organic ozonide. The second arrow represents several steps as shown in ozonolysis.

See also

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References

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  1. ^Cotton, F. A.; Wilkinson, G. (1988).Advanced Inorganic Chemistry (5th ed.). p. 462.
  2. ^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.
  3. ^Klein, W.; Armbruster, K.; Jansen, M. (1998)."Synthesis and crystal structure determination of sodium ozonide".Chemical Communications (6):707–708.doi:10.1039/a708570b.
  4. ^Jansen, Martin; Nuss, Hanne (August 2007). "Ionic Ozonides".Zeitschrift für anorganische und allgemeine Chemie.633 (9):1307–1315.doi:10.1002/zaac.200700023.
  5. ^Wang, Guanjun & Gong, Yu & Zhang, Qingqing & Zhou, Mingfei. "Formation and Characterization of Magnesium Bisozonide and Carbonyl Complexes in Solid Argon". The journal of physical chemistry. A. 114 (2010). 10803-9.https://www.researchgate.net/publication/46392397_Formation_and_Characterization_of_Magnesium_Bisozonide_and_Carbonyl_Complexes_in_Solid_Argon
  6. ^Catherine E. Housecroft; Alan G. Sharpe (2008). "Chapter 16: The group 16 elements".Inorganic Chemistry, 3rd Edition. Pearson. p. 496.ISBN 978-0-13-175553-6.
  7. ^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.ISBN 978-0471936237.
  8. ^Criegee, Rudolf (1975). "Mechanism of Ozonolysis".Angewandte Chemie International Edition in English.14 (11):745–752.doi:10.1002/anie.197507451.
  9. ^Ozonolysis mechanism on Organic Chemistry Portal site

External links

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Mixed oxidation states
+1 oxidation state
+2 oxidation state
+3 oxidation state
+4 oxidation state
+5 oxidation state
+6 oxidation state
+7 oxidation state
+8 oxidation state
Related
Oxides are sorted byoxidation state.Category:Oxides
Compounds of theozonide ion
HO3He
LiO3BeBCNH4O3
N(CH3)4O3
O3FNe
NaO3MgO3
Mg(O3)2
AlSiP(C6H5O)3O3SClAr
KO3CaO3
Ca(O3)2
ScTiVCrMnFeCoNiCuZnGaGeAsSeBrKr
RbO3SrYZrNbMoTcRuRhPdAgCdInSnSbTeIXe
CsO3Ba*LuHfTaWReOsIrPtAuHgTlPbBiPoAtRn
FrRa**LrRfDbSgBhHsMtDsRgCnNhFlMcLvTsOg
 
*LaCePrNdPmSmEuGdTbDyHoErTmYb
**AcThPaUNpPuAmCmBkCfEsFmMdNo
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