A Meisenheimer complex or Jackson–Meisenheimer complex in
organic chemistry is a 1:1 reaction
adduct between an
arene carrying
electron withdrawing group
In chemistry, an electron-withdrawing group (EWG) is a substituent that has some of the following kinetic and thermodynamic implications:
*with regards to electron transfer, electron-withdrawing groups enhance the oxidizing power tendency of the ...
s and a
nucleophile
In chemistry, a nucleophile is a chemical species that forms bonds by donating an electron pair. All molecules and ions with a free pair of electrons or at least one pi bond can act as nucleophiles. Because nucleophiles donate electrons, they are ...
. These complexes are found as
reactive intermediate
In chemistry, a reactive intermediate or an intermediate is a short-lived, high-energy, highly reactive molecule. When generated in a chemical reaction, it will quickly convert into a more stable molecule. Only in exceptional cases can these comp ...
s in
nucleophilic aromatic substitution but stable and isolated Meisenheimer salts are also known.
Background
The early development of this type of complex takes place around the turn of the 19th century. In 1886 Janovski observed an intense violet color when he mixed
''meta''-dinitrobenzene with an alcoholic solution of alkali. In 1895
Cornelis Adriaan Lobry van Troostenburg de Bruyn
Cornelis Adriaan Lobry van Troostenburg de Bruyn (1 January 1857 – 23 July 1904) was a chemist from the Netherlands.
Biography
De Bruyn was born on in Leeuwarden, where his father, Nicholaas Lobry van Troostenburg de Bruyn, was a physician in p ...
investigated a red substance formed in the reaction of
trinitrobenzene Trinitrobenzene may refer to:
* 1,2,3-Trinitrobenzene
*
* 1,3,5-Trinitrobenzene
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