This analysis contrasts kinetic and thermodynamic control in electrophilic substitution of indole, highlighting transition states.
I mentioned in the last post that one can try to predict the outcome of electrophilic aromatic substitution by approximating the properties of the transition state from those of either the reactant or the (presumed Wheland) intermediate by invoking Hammond's postulate. A third option is readily available nowadays; calculate the transition state directly.
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Henry S. Rzepa (2013) studied this question.
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