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

Mile, B.; Morris, Gareth W.; Alcock, William G.

doi:10.1039/p29790001644

Cited by 22 publications

(13 citation statements)

References 4 publications

(5 reference statements)

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“…This is likely due to the slow diffusive exchange of the Criegee zwitterions between two different intermediate pairs on the solid support surface. In contrast, in solution where motion of the fragments is less restricted, such cross-ozonide formation can be significant; While the primary ozonide is not sufficiently stable to be observed, except at low temperatures (43)(44)(45)(46)(47), the secondary ozonides are sufficiently stable that they can be characterized and their rates of decomposition deter- et al (23,24) suggest could be important in the initiation of the autoxidation of lipid in biological systems.…”

Section: Discussionmentioning

confidence: 99%

Formation of secondary ozonides from the reaction of an unsaturated phosphatidylcholine with ozone

Finlayson-Pitts²,

Wv³

1990

Chem. Res. Toxicol.

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Phosphatidylcholines are significant components of pulmonary surfactant in the alveolar region of the lung, where they play a major role in lung function due to their surface tension reducing properties. However, separation and the direct identification of many of the primary products of reaction of phosphatidylcholines with inhaled pollutant gases has not been possible until recently due to the lack of suitable analytical techniques, so that compounds such as fatty acid methyl esters generally have been used as analogues for the phospholipids. We report here the first isolation and identification of the products of reaction of ozone with one of the unsaturated components of lung surfactant, beta-oleoyl-gamma-palmitoyl-L-alpha-phosphatidylcholine (OPPC), using a combination of high-performance liquid chromatography, fast atom bombardment mass spectrometry, and Fourier transform infrared, ultraviolet absorption, and nuclear magnetic resonance spectrometry as well as gas chromatography. The products are shown to be the cis and trans secondary ozonides of the parent phosphatidylcholine, analogous to those previously observed by other researchers in the reactions of the simple fatty acid methyl esters with ozone. This also appears to be the first report of fast atom bombardment mass spectra of these phospholipid secondary ozonides. The implications of this work for the inhalation of ozone, formed in photochemical smog, are discussed.

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Section: Discussionmentioning

confidence: 99%

Formation of secondary ozonides from the reaction of an unsaturated phosphatidylcholine with ozone

Finlayson-Pitts²,

Wv³

1990

Chem. Res. Toxicol.

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“…Their decomposition was studied by IR 96 and 1 H NMR spectroscopy 97 by following the changes in the ozonide concentration and the accumulation of the ozonide transformation products. 98 In all cases studied, the thermolysis of 1,2,3-trioxolanes obeyed the first-order kinetic law.…”

Section: Trioxidesmentioning

confidence: 99%

Thermolysis of organic peroxides in solution

Antonovskiĭ¹,

Хурсан²

2003

Russ. Chem. Rev.

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“…The lifetime of the POZ with respect to thermal decomposition is given by t POZ = 1/k 2 B 100 ms. This can be compared to the studies of Mile et al 79 who measured the kinetics of decomposition of a number of primary ozonides in solution at low temperatures. For decomposition of the POZs of cis-di-isopropylethylene, and of 1-hexene for example, the preexponential factors were estimated to be 10 3 s À1 and the activation energies less than 14 kJ mol…”

Section: à7mentioning

confidence: 99%

A new mechanism for ozonolysis of unsaturated organics on solids: phosphocholines on NaCl as a model for sea salt particles

Karagulian

Lea

Dilbeck

et al. 2008

Phys. Chem. Chem. Phys.

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PERSPECTIVEThe ozonolysis of an approximately one monolayer film of 1-oleoyl-2-palmitoyl-sn-glycero-3-phosphocholine (OPPC) on NaCl was followed in real time using diffuse reflection infrared Fourier transform spectrometry (DRIFTS) at 23 1C. Matrix-assisted laser desorption/ionization (MALDI) mass spectrometry and Auger electron spectroscopy were used to confirm the identification of the products. Ozone concentrations ranged from 1.7 Â 10 12 to 7.0 Â 10 13 molecules cm À3 (70 ppb to 2.8 ppm). Upon exposure to O 3 , there was a loss of CQC accompanied by the formation of a strong band at B1110 cm À1 due to the formation of a stable secondary ozonide (1,2,4-trioxolane, SOZ). The yield of the SOZ was smaller when the reaction was carried out in the presence of water vapor at concentrations corresponding to relative humidities between 2 and 25%.

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

Cited by 22 publications

References 4 publications

Formation of secondary ozonides from the reaction of an unsaturated phosphatidylcholine with ozone

Formation of secondary ozonides from the reaction of an unsaturated phosphatidylcholine with ozone

Thermolysis of organic peroxides in solution

A new mechanism for ozonolysis of unsaturated organics on solids: phosphocholines on NaCl as a model for sea salt particles

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