ChemInform Abstract: Spirocyclic Meisenheimer Complexes. Part 36. Investigation of the Formation of Zwitterionic Spiro‐δ‐Complexes from Polynitroaromatic Derivatives of 3‐Hydroxy‐2‐pyridones, 8‐Hydroxy‐ quinolin‐1‐oxide, Hydroxynaphtho‐ and Anthraquinone.

Knyazev, V. N.; Drozd, V. N.

doi:10.1002/chin.199504169

Cited by 2 publications

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“…This became clear when the absorption spectrum of a solution of ( 52 ) in dichloromethane showed red shifted peaks consistent with a Meisenheimer complex. Also, the H-NMR spectrum of ( 52 ) showed chemical shifts consistent with structure ( 53 ) [ 58 ]. A crystalline sample of ( 52 ) existed only in the ZSMC form ( 53 ).…”

Section: Zwitterionic Spirocyclic Meisenheimer Complexes (Zsmcs)mentioning

confidence: 98%

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Stable Spirocyclic Meisenheimer Complexes

2008

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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 σH-complex 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 σX-complex, 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.

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Section: Zwitterionic Spirocyclic Meisenheimer Complexes (Zsmcs)mentioning

confidence: 98%

“…It is worth mentioning that most of the SMCs synthesized by V. N. Knyazev and co-workers revolved around a similar strategy with slight variations in the chemical structures of the reactants [ 33 , 34 , 35 , 36 , 38 , 39 , 40 , 41 , 42 , 43 , 44 , 45 , 46 , 47 , 50 , 51 , 52 ].…”

Section: B Russian Contributions To Smcsmentioning

confidence: 99%

Stable Spirocyclic Meisenheimer Complexes

2008

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“…Because in general for a zwitterionic spirocyclic Meisenheimer complex the hetero atom which forms bond with the spiro carbon should not possess any positive charge. Because this will make the molecule unstable as the sp 3 carbon will become electron deficient and the system will be keen to rearomatize37. More exciting fact about this molecule was its pH dependent dual fluorescent switching.…”

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confidence: 99%

On-line Ammonia Sensor and Invisible Security Ink by Fluorescent Zwitterionic Spirocyclic Meisenheimer Complex

Das

Pramanik

Haldar

2017

Sci Rep

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Ammonia is not only a highly important gas for civilization but also contribute significantly for climate change and human health hazard. Highly sensitive ammonia sensor has been developed from a fluorescent zwitterionic spirocyclic Meisenheimer complex. Moreover, formation of this Meisenheimer complex can also be utilized for selective as well as naked eye instant detection of nitro aromatic explosive picric acid. The presence of a quaternary nitrogen atom directly attached to the spiro carbon is the unique feature of this Meisenheimer complex. This excellent photoluminescent (PL) Meisenheimer complex has two distinct stimuli responsive sites. One is sensitive towards acid while the other one is towards the base. These two positions can be modulated by adding one equivalent acid and one equivalent base to result two new products which are non fluorescent. One of these two non fluorescent species was found very exciting because of its UV/Vis transparency. Utilizing this concept we have fabricated an on-line sensor for measuring ammonia in dry or humid and condensing sewer air. The sensor was robust against ambient temperature and humidity variation. We have also developed an invisible ink from this Meisenheimer complex, with potential application for security purpose.

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ChemInform Abstract: Spirocyclic Meisenheimer Complexes. Part 36. Investigation of the Formation of Zwitterionic Spiro‐δ‐Complexes from Polynitroaromatic Derivatives of 3‐Hydroxy‐2‐pyridones, 8‐Hydroxy‐ quinolin‐1‐oxide, Hydroxynaphtho‐ and Anthraquinone.

Cited by 2 publications

References 0 publications

Stable Spirocyclic Meisenheimer Complexes

Stable Spirocyclic Meisenheimer Complexes

On-line Ammonia Sensor and Invisible Security Ink by Fluorescent Zwitterionic Spirocyclic Meisenheimer Complex

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