Abstract
The reactivity of phenylnitroso oxide, (p-methylphenyl)nitroso oxide, (p-nitrophenyl)nitroso oxide, (m-nitrophenyl)nitroso oxide, and (p-bromophenyl)nitroso oxide toward a number of olefins in acetonitrile at room temperature was studied using flash photolysis. It was found that the reaction rate constant decreased with decreasing energy of a molecular orbital with a maximum contribution from the atomic orbitals of carbon atoms in the C=C bond of olefins. This, along with a positive slope of the Hammett function for the reactions of substituted phenylnitroso oxides with 1-hexene and styrene, suggest an electrophilic character of these species. The temperature dependence of the rate constant of the reaction of phenylnitroso oxide with 1-hexene was studied: log A = 7.9 ± 0.4 [l mol-1 s-1]; Ea = 38 ± 2 kJ/mol.
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