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Meisenheimer adduct definition

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A cyclohexadienyl derivative formed as Lewis adduct from a nucleophile (Lewis base) and an aromatic or heteroaromatic compound, also called Jackson-Meisenheimer adduct. In earlier usage the term "Meisenheimer complex" was restricted to the typical Meisenheimer alkoxide adducts of nitro-substituted aromatic ethers, e.g.,

Analogous cationic adducts, such as

considered to be reaction intermediates in electrophilic aromatic substitution reactions, are called "Wheland intermediates", and sometimes, inappropriately, -complexes. JACKSON and GAZZOLO (1900); BUNCEL, CRAMPTON, STRAUSS and TERRIER. (1984). See also -adduct.

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