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Issue 12, 1979
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Infrared spectra and kinetics of decomposition of primary ozonides in the liquid phase at low temperatures

Abstract

A low-temperature i.r. cell has been developed for in situ studies of the intermediates of the ozonolysis of alkenes in the liquid phase at temperatures down to –178°C. The i.r. spectra of 1,2,3-trioxolans (primary ozonides) formed from the following alkenes have been observed: hex-1-ene, cis-di-isopropylethylene, trans-diethylethylene, trans-di-isopropylethylene, and trans-di-t-butylethylene. All have characteristic bands in three spectral regions, 690, 970, and 1 100 cm–1 and at higher temperatures decompose with the formation of 1,2,4-trioxolans (final ozonide) and peroxy-compounds. The decay of the i.r. bands at 690 cm–1 has been used to study the kinetics of the decomposition of the primary ozonides over a range of temperatures. The reactions are first order and have the following A and E factors: trans-diethylethylene, 105.3 s–1, 29 ± 6 kJ mol–1; trans-di-isopropylethylene, 108.4 s–1, 40 ± 3 kJ mol–1; trans-di-t-butylethylene, 1011 s–1, 60 ± 13 kJ mol–1. The activation energies for the decomposition of the primary ozonides from cis-di-isopropylethylene and hex-1-ene are estimated to be lower than 14 kJ mol–1. The observed parameters and the effects of substitution indicate incipient π-bonding and charge separation in the C–O bonds of the transition state and also considerable orientation of solvent molecules.

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Article information


J. Chem. Soc., Perkin Trans. 2, 1979, 1644-1652
Article type
Paper

Infrared spectra and kinetics of decomposition of primary ozonides in the liquid phase at low temperatures

B. Mile, G. W. Morris and W. G. Alcock, J. Chem. Soc., Perkin Trans. 2, 1979, 1644
DOI: 10.1039/P29790001644

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