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Molecules 2008, 13(6), 1282-1302; doi:10.3390/molecules13061282

Stable Spirocyclic Meisenheimer Complexes

Department of Basic Sciences, King Saud Bin Abdulaziz University for Health Sciences-National, Riyadh, Central Province, Saudi Arabia
Departament de Química, Universitat Autònoma de Barcelona, 08193-Bellaterra, Barcelona, Spain
Authors to whom correspondence should be addressed.
Received: 15 May 2008 / Revised: 6 June 2008 / Accepted: 6 June 2008 / Published: 9 June 2008
(This article belongs to the Special Issue Spiro Compounds)


Meisenheimer complexes are important intermediates in Nucleophilic Aromatic Substitution Reactions (SNAr). They are formed by the addition of electron rich species to polynitro aromatic compounds or aromatic compounds with strong electron withdrawing groups. It is possible to distinguish two types of Meisenheimer or σ-complexes, the σHcomplex or σX-complex (also named ipso), depending on the aromatic ring position attacked by the nucleophile (a non-substituted or substituted one, respectively). Special examples of σX- or ipso-complexes are formed through intermediate spiro adducts, via intramolecular SNAr. Some of these spirocyclic Meisenheimer complexes, a type of σXcomplex, are exceptionally stable in solution and/or as solids. They can be isolated and characterized using X-ray, and various spectroscopic techniques such as NMR, UV-Vis, IR, and fluorescence. A few of these stable spirocyclic Meisenheimer complexes are zwitterionic and exhibit interesting photophysical and redox properties. We will review recent advances, synthesis and potential applications of these stable spirocyclic Meisenheimer complexes.
Keywords: Spirocyclic-; Zwitterionic-; Meisenheimer- Complexes; Fluorescent Compounts Spirocyclic-; Zwitterionic-; Meisenheimer- Complexes; Fluorescent Compounts
This is an open access article distributed under the Creative Commons Attribution License (CC BY 3.0).

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Al-Kaysi, R.O.; Gallardo, I.; Guirado, G. Stable Spirocyclic Meisenheimer Complexes. Molecules 2008, 13, 1282-1302.

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