Abstract:Gas phase ion-molecule reactions between seleniranium
ions, R-c-SeCH2CH2
+, and cis-cyclooctene were used to probe electronic
and steric
effects of substituents on kinetics and branching ratios. The second-order
rate coefficients increased in the order p-OMeC6H4 < C6H5 < p-BrC6H4 < p-CF3C6H4 < m-NO2C6H4, giving a Hammett plot with R
2 = 0.98 and ρ = +1.66. The two main pathways
include direct transfer of the selenium moiety to the incoming alkene
(π-ligand exchange) and the less favored ring-opening by attack
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