Active Oxygen in Chemistry by Raymond Y. N. Ho, Joel F. Liebman, Joan Selverstone

By Raymond Y. N. Ho, Joel F. Liebman, Joan Selverstone Valentine (auth.), Christopher S. Foote, Joan Selverstone Valentine, Arthur Greenberg, Joel F. Liebman (eds.)

Taking an interdisciplinary method, this booklet and its counterpart, Active Oxygen in Biochemistry, discover the lively examine region of the chemistry and biochemistry of oxygen. Complementary yet autonomous, the 2 volumes combine topic parts together with medication, biology, chemistry, engineering, and environmental studies.

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46 Autoxidation THE HYDROPEROXYL (HOO·) CHAIN Because O2 is a triplet with some diradical properties, its reaction with R· can be thought of as a radical coupling, and a radical disproportion to give HOO· and olefin should also be possible. As we shall see, such a reaction path becomes significant at high temperatures, but in suitable cases it can also be important near room temperature. A good example (Howard and Ingold, 1967a) is l,4-cyclohexadiene, which oxidizes cleanly to benzene and H 20 2 via the sequence -0 0 -0 0+ 02 HH HOO-+ +HOO- +H20 2 (2-36) (2-37) H H Here the driving force for the disproportionation (2-36)-(2-37) is presumably the formation of the stable aromatic system, and it is likely that other oxidative aromatizations occur similarly.

22 Overview of the Energetics and Reactivity of Oxygen GEORGE, P. (1965) The Fitness of Oxygen, in Oxidases and Related Redox Systems (T. E. King, H. S. Mason, and M. ), John WIley & Sons, New York, pp. 3-36. GLASGOW, L. C. (1975) Ozone Equipment and Instrumentation, in Ozone Chemistry and Technology S. Murphy and J. R. ), Franklin Institute Press, Philadelphia, 133-161. HUBER, K. , and HERZBERG, G. (1979) Molecular Spectra and Molecular Structure Constants of Diatomic Molecules, Van Nostrand, New York.

H. (1958) Tables of Interatomic Distances and Configuration in Molecules and Ions, The Chemical Society, London. , and SANDERS, J. c. P. (1988) From Atoms to Polymers: Isoelectronic Analogies, VCH, New York. , and PLESNICAR, B. (1993) Characterization and Reactivity of Hydrogen Trioxide (HOOOH): A Reactive Intermediate Formed in the Low Temperature Ozonation of 2-Ethylanthrahydroquinone. J. Am. Chem. , 115, 12169-12170. COTTON, A. , and WILKINSON, G. (1988) Advanced Inorganic Chemistry, Vol. 5, John Wlley and Sons, New York.

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