This analysis reports the impact of resonance structures on regiospecificity in aromatic systems, suggesting a novel predictive approach.
Every introductory course or text on aromatic electrophilic substitution contains an explanation along the lines of the resonance diagram shown below. With an o/p directing group such as NH2, it is argued that negative charge accumulates in those positions as a result of the resonance structures shown.
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Henry S. Rzepa (2009) studied this question.
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