A Meisenheimer complex or Jackson–Meisenheimer complex in

organic chemistry Organic chemistry is a subdiscipline within chemistry involving the scientific study of the structure, properties, and reactions of organic compounds and organic materials, i.e., matter in its various forms that contain carbon atoms.Clayden, J.; ...

is a 1:1 reaction

adduct An adduct (from the Latin ''adductus'', "drawn toward" alternatively, a contraction of "addition product") is a product of a direct addition of two or more distinct molecules, resulting in a single reaction product containing all atoms of all co ...

between an

arene Aromatic compounds, also known as "mono- and polycyclic aromatic hydrocarbons", are organic compounds containing one or more aromatic rings. The parent member of aromatic compounds is benzene. The word "aromatic" originates from the past grouping ...

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 ...

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 A nucleophilic aromatic substitution is a substitution reaction in organic chemistry in which the nucleophile displaces a good leaving group, such as a halide, on an aromatic ring. Aromatic rings are usually nucleophilic, but some aromatic compou ...

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 {{Short pages monitor