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Meisenheimer Complexes in S N Ar Reactions: Intermediates or Transition States?
Author(s) -
Lennox Alastair J. J.
Publication year - 2018
Publication title -
angewandte chemie international edition
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 5.831
H-Index - 550
eISSN - 1521-3773
pISSN - 1433-7851
DOI - 10.1002/anie.201809606
Subject(s) - chemistry , transition state , nucleophilic aromatic substitution , kinetic isotope effect , computational chemistry , reaction intermediate , reactive intermediate , nucleophilic substitution , medicinal chemistry , organic chemistry , catalysis , deuterium , physics , quantum mechanics
Meisenheimer's missing ! Anionic σ‐complexes, best known as Meisenheimer complexes, have long been assumed to be intermediates in S N Ar reactions. New evidence now suggests that these intermediates may only be formed in select cases and that a concerted pathway is more common. These claims are supported by 12 C/ 13 C kinetic isotopes effects, determined using a new method based on 19 F NMR, and DFT calculations.