Meisenheimer adduct

https://doi.org/10.1351/goldbook.M03819
A cyclohexadienyl derivative formed as @L03510@ from a nucleophile (@L03511@) and an @A00441@ or heteroaromatic compound, also called Jackson–Meisenheimer @A00138@. In earlier usage the term 'Meisenheimer complex' was restricted to the typical Meisenheimer alkoxide @A00138@ of nitro-substituted aromatic @E02221@, e.g.
M03819-1.png
Analogous cationic adducts, such as:
M03819-2.png
considered to be @R05171@ in @E02020@ aromatic @S06078@, are called 'Wheland intermediates', and sometimes, inappropriately, σ-complexes.
See also:
σ-adduct
Source:
PAC, 1994, 66, 1077. (Glossary of terms used in physical organic chemistry (IUPAC Recommendations 1994)) on page 1138 [Terms] [Paper]
See also:
PAC, 1995, 67, 1307. (Glossary of class names of organic compounds and reactivity intermediates based on structure (IUPAC Recommendations 1995)) on page 1348 [Terms] [Paper]
Citation: 'Meisenheimer adduct' in IUPAC Compendium of Chemical Terminology, 3rd ed. International Union of Pure and Applied Chemistry; 2006. Online version 3.0.1, 2019. https://doi.org/10.1351/goldbook.M03819 RIS BibTex EndNote
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Last revised: February 24, 2014