Stable Spirocyclic Meisenheimer Complexes
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 o...
| Main Authors: | , , |
|---|---|
| Format: | Article |
| Language: | English |
| Published: |
MDPI AG
2008-06-01
|
| Series: | Molecules |
| Subjects: | |
| Online Access: | http://www.mdpi.com/1420-3049/13/6/1282/ |
| _version_ | 1819169857226145792 |
|---|---|
| author | Gonzalo Guirado Iluminada Gallardo Rabih O. Al-Kaysi |
| author_facet | Gonzalo Guirado Iluminada Gallardo Rabih O. Al-Kaysi |
| author_sort | Gonzalo Guirado |
| collection | DOAJ |
| description | 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 Ã-complexes, the ÃHcomplex or ÃX-complex (also named ipso), depending on the aromatic ring position attacked by the nucleophile (a non-substituted or substituted one, respectively). Special examples of ÃX- or ipso-complexes are formed through intermediate spiro adducts, via intramolecular SNAr. Some of these spirocyclic Meisenheimer complexes, a type of ÃXcomplex, 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. |
| first_indexed | 2024-12-22T19:26:09Z |
| format | Article |
| id | doaj.art-55945a3dc9eb48cd9887e858bae7cff8 |
| institution | Directory Open Access Journal |
| issn | 1420-3049 |
| language | English |
| last_indexed | 2024-12-22T19:26:09Z |
| publishDate | 2008-06-01 |
| publisher | MDPI AG |
| record_format | Article |
| series | Molecules |
| spelling | doaj.art-55945a3dc9eb48cd9887e858bae7cff82022-12-21T18:15:14ZengMDPI AGMolecules1420-30492008-06-011361282130210.3390/molecules13061282Stable Spirocyclic Meisenheimer ComplexesGonzalo GuiradoIluminada GallardoRabih O. Al-KaysiMeisenheimer 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 Ã-complexes, the ÃHcomplex or ÃX-complex (also named ipso), depending on the aromatic ring position attacked by the nucleophile (a non-substituted or substituted one, respectively). Special examples of ÃX- or ipso-complexes are formed through intermediate spiro adducts, via intramolecular SNAr. Some of these spirocyclic Meisenheimer complexes, a type of ÃXcomplex, 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.http://www.mdpi.com/1420-3049/13/6/1282/Spirocyclic-Zwitterionic-Meisenheimer- ComplexesFluorescent Compounts |
| spellingShingle | Gonzalo Guirado Iluminada Gallardo Rabih O. Al-Kaysi Stable Spirocyclic Meisenheimer Complexes Molecules Spirocyclic- Zwitterionic- Meisenheimer- Complexes Fluorescent Compounts |
| title | Stable Spirocyclic Meisenheimer Complexes |
| title_full | Stable Spirocyclic Meisenheimer Complexes |
| title_fullStr | Stable Spirocyclic Meisenheimer Complexes |
| title_full_unstemmed | Stable Spirocyclic Meisenheimer Complexes |
| title_short | Stable Spirocyclic Meisenheimer Complexes |
| title_sort | stable spirocyclic meisenheimer complexes |
| topic | Spirocyclic- Zwitterionic- Meisenheimer- Complexes Fluorescent Compounts |
| url | http://www.mdpi.com/1420-3049/13/6/1282/ |
| work_keys_str_mv | AT gonzaloguirado stablespirocyclicmeisenheimercomplexes AT iluminadagallardo stablespirocyclicmeisenheimercomplexes AT rabihoalkaysi stablespirocyclicmeisenheimercomplexes |