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Meisenheimer adduct

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.
M03819-1
Analogous cationic adducts, such as:
M03819-2
considered to be reaction intermediates in electrophilic aromatic substitution reactions, 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
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
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IUPAC. Compendium of Chemical Terminology, 2nd ed. (the "Gold Book"). Compiled by A. D. McNaught and A. Wilkinson. Blackwell Scientific Publications, Oxford (1997). XML on-line corrected version: http://goldbook.iupac.org (2006-) created by M. Nic, J. Jirat, B. Kosata; updates compiled by A. Jenkins. ISBN 0-9678550-9-8. https://doi.org/10.1351/goldbook.
Last update: 2014-02-24; version: 2.3.3.
DOI of this term: https://doi.org/10.1351/goldbook.M03819.
Original PDF version: http://www.iupac.org/goldbook/M03819.pdf. The PDF version is out of date and is provided for reference purposes only. For some entries, the PDF version may be unavailable.
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