Ozonide

Ozonide

Ozonide is an unstable, reactive polyatomic anion O3−, derived from ozone, or an organic compound similar to organic peroxide formed by a reaction of ozone with an unsaturated compound.

Contents

Inorganic ozonides

Inorganic ozonides[1] are dark red ionic compounds containing the reactive O3− anion. The anion has the V shape of the ozone molecule.

Inorganic ozonides are formed by burning potassium or heavier alkali metals in ozone, or by treating the alkali metal hydroxide with ozone; if potassium is left undisturbed in air for years it accumulates a covering of superoxide and ozonide. 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 unstable and must be prepared by low-temperature ion exchange starting from CsO3. Sodium ozonide, NaO3, which is prone to decompose 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 NaO3 may be obtained as red crystals isostructural to NaNO2.[3]

Inorganic ozonides are being investigated as promising sources of oxygen in chemical oxygen generators.

Organic ozonides

Organic ozonides are more explosive cousins of the organic peroxides formed by addition reactions of ozone and unsaturated compounds. They are intermediates in ozonolysis and have a trioxolane ring structure with a five-membered C-O-O-C-O ring.[4][5] 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. Due to their instability, they are rarely isolated during the course of the ozonolysis reaction sequence.

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

See also

References

  1. ^ F.A. Cotton and G. Wilkinson "Advanced Inorganic Chemistry", 5th edition (1988), 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.  edit
  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. http://www.rsc.org/delivery/_ArticleLinking/DisplayArticleForFree.cfm?doi=a708570b&JournalCode=CC.  edit
  4. ^ Criegee, R. Angew. Chem. Int. Ed. Engl. 1975, 87, 745-752. (doi:10.1002/anie.197507451)
  5. ^ http://www.organic-chemistry.org/namedreactions/ozonolysis-criegee-mechanism.shtm Ozonolysis mechanism on Organic Chemistry Portal site

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  • ozonide — ● ozonide nom masculin Dénomination courante des produits secondaires de l addition de l ozone sur les alcènes …   Encyclopédie Universelle

  • Ozonide — Ozonide,   Singular Ozonid das, (e)s, 1) Salze mit dem Anion O3 , die sich bei der Einwirkung von Ozon auf trockene Alkalihydroxide bilden; 2) organische Verbindungen, die bei Anlagerung von Ozon an Verbindungen mit Doppelbindungen entstehen… …   Universal-Lexikon

  • ozonide — [ō′zō nīd΄, ō′zənīd΄] n. any of a series of compounds formed by the action of ozone on unsaturated organic compounds …   English World dictionary

  • Ozonide — Un ozonide est soit : l anion instable, O3−, dérivé de l ozone un composé organique RO3 semblable à un peroxyde organique formé par réaction de l ozone et d un composé insaturé. Portail de la chimie …   Wikipédia en Français

  • ozonide — /oh zeuh nuyd , oh zoh /, n. Chem. any compound, usually explosive, formed by the addition of ozone to the double or triple bond of an organic compound. [1865 70; OZON + IDE] * * * ▪ chemical compound       any of a class of chemical compounds… …   Universalium

  • ozonide — noun Date: 1867 a compound formed by the addition of ozone to a double or triple bond of an organic compound …   New Collegiate Dictionary

  • ozonide — noun a) the univalent anion, O, derived from ozone b) any dark red salt of this anion and a metal …   Wiktionary

  • ozonide — The unstable intermediate formed by the reaction of ozone with an unsaturated organic compound, especially with unsaturated fatty acid s. * * * ozon·ide ō (.)zō .nīd n a compound of ozone specif a compound formed by the add …   Medical dictionary

  • ozonide — n. organic compound containing ozone …   English contemporary dictionary

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