Sonia Aggarwal - University of Ottawa

Placement: University of Toronto
Supervisor: Dr. Bob McClelland


The Effects of Conjugation to Polycyclic Aromatic Rings on the Reactivity of Benzylic-Type Cations

A series of seven -arylbenzyl acetates, in which the aryl group was a polycyclic aromatic hydrocarbon (PAH), were synthesized. These compounds were irradiated using laser flash photolysis, giving the -arylbenzyl cations, and the rates of decay of the cations were determined. Upon analysis of the data it was found that the size and structure of the PAH had a significant effect on the rate. A simple graph of log kdecay versus the number of ring resonance structures showed a linear relation - the greater the number of contributors the more stable the cation. From this study, I conclude that benzyl-type cations derived from carcinogenic PAH's such as benzo[a]pyrene are quite long-lived because of the large number of resonance contributors that they have.


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18-sep-97