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Robert Paton
Associate Professor, Oxford.
Associate Professor, Oxford.
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Robert Paton commented on a post on Blogger.
This method works since you are essentially describing the dearomatized intermediate which, by the Hammond postulate, resembles the TS. Instead of proton affinity, you could look at the electrophile affinity (e.g. Br+ http://pubs.acs.org/doi/abs/10.1021/jo902730g) - this may be slightly more accurate if there are any steric effects not captured by using a proton.

Also, presumably it is the greatest (and not lowest) proton affinity which implies more favourable protonation, and so corresponds to the most nucleophilic/reactive position?
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