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A Meisenheimer complex is a negatively charged intermediate formed by the attack of a nucleophile upon one of the aromatic-ring carbons during the course of a nucleophilic aromatic substitution reaction. A typical Meisenheimer complex is shown in the reaction scheme below.
16 de jul. de 2018 · The Meisenheimer model for predicting the principal site of for nucleophilic substitution in aromatic perfluorocarbons—generalization to include ring-nitrogen atoms and non-fluorine ring ...
- Eugene E. Kwan, Yuwen Zeng, Harrison A. Besser, Eric N. Jacobsen
- 2018
A Meisenheimer complex or Jackson–Meisenheimer complex in organic chemistry is a 1:1 reaction adduct between an arene carrying electron withdrawing groups and a nucleophile. These complexes are found as reactive intermediates in nucleophilic aromatic substitution but stable and isolated Meisenheimer salts are also known.
1 de nov. de 2020 · Cuando el compuesto aromático contiene grupos aceptores de electrones y un halógeno con nucleófilo ataca el carbono unido al halógeno, forma un intermedio de carbanión que se estabiliza en estructuras de resonancia, conocido como complejo de Meisenheimer.
Some of these spirocyclic Meisenheimer complexes, a type of σXcomplex, are exceptionally stable in solution and/or as solids. They can be isolated and characterized using X-ray, and various spectroscopic techniques such as NMR, UV-Vis, IR, and fluorescence.
- Rabih O. Al-Kaysi, Iluminada Gallardo, Gonzalo Guirado
- 2008
This chapter discusses Meisenheimer complexes. Spectroscopic and crystallographic methods have largely confirmed Meisenheimer's formula for the stable adducts from alkyl picrates and alkoxides. Meisenheimer associated with the para-nitro group is delocalized about the ring and in the nitro-groups.
Pearson et al. describe the structure-guided discovery of benzothiazole N-oxide PLK1 inhibitors that bind covalently with C67 through Meisenheimer complexes. These represent prototypes to exploit this unique mechanism of inhibition in drug discovery to achieve high specificity and still bind reversibly.
