Journal of Organic Chemistry p. 4198 - 4202 (1983)
Update date:2022-08-17
Topics:
Pryor, William A.
Gleicher, Gerald J.
Church, Daniel F.
Nine unsubstituted, polycyclic aromatic hydrocarbons were allowed to react with ozone at 25 deg C, and relative rate constants were obtained by direct competitive techniques.The rate constants show a large variation with substrate structure, with nearly three powers of ten difference between the least reactive (benzene) and most reactive (anthracene, perylene) compounds studied.Linear free-energy relationships between the rate data and calculated molecular orbital parameters have been obtained.The optimum correlations are found for models based on rate-determining ?-complex or ?-complex formation rather than simultaneous addition of ozone to two carbon atoms.Electrophilic attack by ozone to yield a ?-complex also appears to be the rate-determining step based on the results obtained for changes in selectivity with variation of solvents.
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