Meisenheimer Complexes in SNAr Reactions: Intermediates or Transition States?

Alastair J. J. Lennox

doi:10.1002/anie.201809606

Meisenheimer Complexes in SNAr Reactions: Intermediates or Transition States?

Alastair J. J. Lennox

School of Chemistry

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Abstract

Meisenheimer's missing! Anionic σ‐complexes, best known as Meisenheimer complexes, have long been assumed to be intermediates in SNAr 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 12C/13C kinetic isotopes effects, determined using a new method based on 19F NMR, and DFT calculations.

Original language	English
Pages (from-to)	14686-14688
Number of pages	3
Journal	Angewandte Chemie - International Edition
Volume	57
Issue number	45
Early online date	15 Oct 2018
DOIs	https://doi.org/10.1002/anie.201809606
Publication status	Published - 5 Nov 2018

Keywords

concerted reactions
density functional calculations
kinetic isotope effect
mechanistic studies
nucleophilic aromatic substitution

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title = "Meisenheimer Complexes in SNAr Reactions: Intermediates or Transition States?",

abstract = "Meisenheimer's missing! Anionic σ‐complexes, best known as Meisenheimer complexes, have long been assumed to be intermediates in SNAr 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 12C/13C kinetic isotopes effects, determined using a new method based on 19F NMR, and DFT calculations.",

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N2 - Meisenheimer's missing! Anionic σ‐complexes, best known as Meisenheimer complexes, have long been assumed to be intermediates in SNAr 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 12C/13C kinetic isotopes effects, determined using a new method based on 19F NMR, and DFT calculations.

AB - Meisenheimer's missing! Anionic σ‐complexes, best known as Meisenheimer complexes, have long been assumed to be intermediates in SNAr 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 12C/13C kinetic isotopes effects, determined using a new method based on 19F NMR, and DFT calculations.

KW - concerted reactions

KW - density functional calculations

KW - kinetic isotope effect

KW - mechanistic studies

KW - nucleophilic aromatic substitution

U2 - 10.1002/anie.201809606

DO - 10.1002/anie.201809606

M3 - Review article (Academic Journal)

C2 - 30320484

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JO - Angewandte Chemie - International Edition

JF - Angewandte Chemie - International Edition

IS - 45

ER -

Meisenheimer Complexes in SNAr Reactions: Intermediates or Transition States?

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