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2007 | 5 | 1 | 71-86
Tytuł artykułu

Matrix isolation FTIR spectroscopical study of ethene secondary ozonide

Treść / Zawartość
Warianty tytułu
Języki publikacji
EN
Abstrakty
EN
A new method is used for the separation of ethene secondary ozonide (SOZ) from the other products of ethene ozonization reaction. The reaction was performed in the neat films of the reactants at 77 K. Ethene SOZ was separated from other products of the reaction by vacuum distillation at 190–210 K and analyzed by means of the matrix isolation IR absorption spectroscopy. Spectroscopic data from photolysis of the matrix isolated ozonide was used as an argument for assignment of the infrared spectral bands either to ethene SOZ or to other products of the reaction. The spectra of ethene SOZ isolated in the Ar matrix were analyzed by combining experimental results with the theoretical calculations performed at the MP2 6-311+G (3df, 3pd) level. A new assignment of some experimental fundamental bands is proposed taking in to account the Fermi resonance between CH stretch and the five membered ring vibrations. For the first time more than 30 weak infrared absorption bands were observed and assigned to various combination vibrations and overtones. By using new spectral information concerning the overtones and the combination bands it is concluded that the dissociation of unstable ethene SOZ involving breaking of any of the four CO bonds of the five membered ring of ethene SOZ has low probability. Dissociation of the ring starts from breaking of the OO bond. [...]
Wydawca
Czasopismo
Rocznik
Tom
5
Numer
1
Strony
71-86
Opis fizyczny
Daty
wydano
2007-03-01
online
2007-03-01
Twórcy
  • Department of General Physics and Spectroscopy, Vilnius University, Vilnius, 01513, Lithuania
  • Department of General Physics and Spectroscopy, Vilnius University, Vilnius, 01513, Lithuania
Bibliografia
  • [1] R. Criegee: “The course of ozonization of unsaturated compounds”, Rec. Chem. Prog., Vol. 18, (1957), pp. 111–120.
  • [2] B. Nelander and L. Nord: “The reaction between ethylene and ozone. A matrix study”, Tetrahedron Lett., Vol. 32 (1977), pp. 2821–2822. http://dx.doi.org/10.1016/S0040-4039(01)83083-5[Crossref]
  • [3] B. Nelander and L. Nord: “Do ozone-olefin complexes really exist?”, J. Am. Chem. Soc., Vol. 101 (1979), pp. 3769–3770. http://dx.doi.org/10.1021/ja00508a011[Crossref]
  • [4] H. Niki, P.D. Maker, C.M. Savage and L.P. Breitenbach: “A FT study of a transitory product in gas-phase ozone-ethylene reaction”, J. Chem. Phys., Vol. 85, (1981), pp. 1024–1027. http://dx.doi.org/10.1021/j150608a020[Crossref]
  • [5] M. Hawkins, C.K. Kohlmiller and L. Andrews: “Matrix infrared spectra and photolysis and pyrolysis of isotopic secondary ozonides of ethylene”, J. Phys. Chem., Vol. 86, (1982), pp. 3154–3166. http://dx.doi.org/10.1021/j100213a019[Crossref]
  • [6] R. Atkinson, E.C. Tuazon and S.M. Aschmann: “Products of the gas-phase reactions of O3 with alkenes”, Environmental Science & Technology, Vol. 29 (1995), pp. 1860–1866. http://dx.doi.org/10.1021/es00007a025[Crossref]
  • [7] U. Samuni and Y. Haas: “An ab-initio study of the normal modes of the primary and secondary ozonides of ethylene”, Spectrochim. Acta, Vol. A 52, (1996), pp. 1479–1492.
  • [8] U. Samuni, R. Fraenkel, Y. Haas, R. Fajgar and J. Pola: “Environmental effects on the formation of the primary and secondary ozonides of ethylene at cryogenic temperatures”, J. Am. Chem. Soc., Vol. 118, (1996), pp. 3687–3693. http://dx.doi.org/10.1021/ja9532852[Crossref]
  • [9] R. Fajgar, J. Vitek, Y. Haas and J. Pola: “Formation of secondary ozonides in the gas phase low-temperature ozonation of primary and secondary alkenes”, J. Chem. Soc. Perkin Trans. 2, (1999), pp. 239–248. [Crossref]
  • [10] E.J. Feltham, M.J. Almond, G. Marston, V.P. Ly and K.S. Wiltshire: “Reactions of alkenes with ozone in the gas phase: a matrix-isolation study of secondary ozonides and carbonyl-containing reaction products”, Spectrochim. Acta, Vol. A56, (2000), pp. 2605–2616.
  • [11] J.M. Anglada, R. Crehuet and J.M. Bofill: “The ozonolysis of ethylene: a theoretical study of the gas-phase reaction mechanism”, Chem. Eur. J., Vol. 5, (1999), pp. 1809–1822. http://dx.doi.org/10.1002/(SICI)1521-3765(19990604)5:6<1809::AID-CHEM1809>3.0.CO;2-N[Crossref]
  • [12] C.W. Gillies and R.L. Kuczkowski: “Mechanism of ozonolysis. Microwave spectrum, structure, and dipole moment of ethylene ozonide”, J. Amer. Chem. Soc., Vol. 94, (1972), pp. 6337–6343. http://dx.doi.org/10.1021/ja00773a014[Crossref]
  • [13] P.S. Bailey and T.M. Ferell: “Mechanism of ozonolysis. A more flexible stereochemical concept”, J. Am. Chem. Soc., Vol. 100, (1978), pp. 899–905. http://dx.doi.org/10.1021/ja00471a040[Crossref]
  • [14] H. Kühne and Hs.H. Günthard: “Spectroscopic study of the ozone-ethylene reaction. Matrix infrared spectra of three isotopic ethylene ozonides”, J. Phys. Chem., Vol. 80, (1976), pp. 1238–1247. http://dx.doi.org/10.1021/j100552a025[Crossref]
  • [15] L. Khachatryan, Y. Hass and J. Pola: “Laser-induced decomposition of 3,5-dimethyl-1,2,4-trioxolane (secondary butene-2-ozonide) in the gas phase”, J. Chem. Soc., Perkin Trans. 2, (1997), pp. 1147–1151. [Crossref]
  • [16] R. Bariseviciute, J. Ceponkus, A. Gruodis and V. Sablinskas: “Conformational studies of aliphatic secondary ozonides (propene, 1-butene and 1-heptene) by means of FTIR spectroscopy”, Cent. Eur. J. Chem., Vol. 4, (2006), pp. 1–14. http://dx.doi.org/10.2478/s11532-006-0031-3[Crossref]
  • [17] V. Sablinskas, F. Hegelund, J. Ceponkus, R. Bariseviciute, V. Aleksa and B. Nelander: “A high resolution FT-IR study of the fundamental bands v7, v8 and v18 of ethene secondary ozonide”, J. Phys. Chem. A, Vol. 109, (2005), pp. 8719–8723. http://dx.doi.org/10.1021/jp051647e[Crossref]
  • [18] J.M. Hollas: Modern spectroscopy, John Wiley & Sons, 1996, p. 416.
  • [19] P.W. Atkins, P.W. Atkins and R.S. Friedman: Molecular quantum mechanics, Oxford University Press, 2005, p. 588.
  • [20] L.A. Hull, I.C. Hisatsune and J. Heicklen: “Vapor-phase thermal decomposition of some simple ozonides”, J. Phys. Chem., Vol. 76, (1972), pp. 2659–2665. http://dx.doi.org/10.1021/j100663a003[Crossref]
Typ dokumentu
Bibliografia
Identyfikatory
Identyfikator YADDA
bwmeta1.element.-psjd-doi-10_2478_s11532-006-0073-6
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