Abstract
Organic Chemistry Displacement reactions at saturated carbons often proceed by a concerted mechanism: A new bond forms at the same time as the old bond breaks. In aromatic rings, Meisenheimer complexes have been characterized with the incoming group bound before the leaving group departs, so a two-step mechanism is the default assumption. Kwan et al. now report that this assumption usually does not hold. They measured carbon kinetic isotope effects of several nucleophilic aromatic substitutions by using a sensitive 19F nuclear magnetic resonance technique; they then benchmarked theoretical methods for a much broader virtual study. The net result was that 83% of 120 simulated reactions were concerted. Nat. Chem. 10.1038/s41557-018-0079-7 (2018).
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