Next Article in Journal
Unusual Regioselectivity in the Opening of Epoxides by Carboxylic Acid Enediolates
Next Article in Special Issue
Chemical and Enzymatic Approaches to Carbohydrate-Derived Spiroketals: Di-D-Fructose Dianhydrides (DFAs)
Previous Article in Journal
A New Sesquiterpenoid Hydroquinone from the Marine Sponge Dysidea arenaria
Previous Article in Special Issue
Density Functional Theory Study of the Trans-Trans-Cis (TTC)→Trans-Trans-Trans (TTT) Isomerization of a Photochromic Spiropyran Merocyanine
Molecules 2008, 13(6), 1282-1302; doi:10.3390/molecules13061282
Review

Stable Spirocyclic Meisenheimer Complexes

1,* , 2 and 2,*
1 Department of Basic Sciences, King Saud Bin Abdulaziz University for Health Sciences-National, Riyadh, Central Province, Saudi Arabia 2 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)
Download PDF [168 KB, uploaded 18 June 2014]

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.
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 which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited.

Share & Cite This Article

Export to BibTeX |
EndNote


MDPI and ACS Style

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

View more citation formats

Related Articles

Article Metrics

Comments

Citing Articles

[Return to top]
Molecules EISSN 1420-3049 Published by MDPI AG, Basel, Switzerland RSS E-Mail Table of Contents Alert