Stable Spirocyclic Meisenheimer Complexes
Al-Kaysi, Rabih O. (King Saud Bin Abdulaziz University for Health Sciences. Department of Basic Sciences)
Gallardo, Iluminada (Universitat Autònoma de Barcelona. Departament de Química)
Guirado López, Gonzalo (Universitat Autònoma de Barcelona. Departament de Química)

Date:	2008
Abstract:	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.
Rights:	Aquest document està subjecte a una llicència d'ús Creative Commons. Es permet la reproducció total o parcial, la distribució, la comunicació pública de l'obra i la creació d'obres derivades, fins i tot amb finalitats comercials, sempre i quan es reconegui l'autoria de l'obra original.
Language:	Anglès
Document:	Article ; recerca ; Versió publicada
Subject:	Spirocyclic- ; Zwitterionic- ; Meisenheimer- Complexes ; Fluorescent Compounds
Published in:	Molecules, Vol. 13 Núm. 6 (June 2008) , p. 1282-1302, ISSN 1420-3049

DOI: 10.3390/molecules13061282
PMID: 18596655

21 p, 167.9 KB

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Research literature > UAB research groups literature > Research Centres and Groups (research output) > Experimental sciences > Group in Electrochemistry, Photochemistry and Organic Reactivity (GEFRO)
Articles > Research articles
Articles > Published articles