Diazenium Betaines Derived from the Stable Free Radical DPPH with Diradicaloid Behavior

Starting from the well known stable free radical DPPH (or its reduced counterpart, 2,2-diphenyl-1-picryl-hydrazine) and several amino derivatives, novel zwitterionic compounds (diazenium betaines) were obtained and characterized by different means, like NMR, IR, MS, and UV–Vis. These betaines are hi...

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Bibliographic Details
Published in:Chemistry an international journal 2024-10, Vol.6 (5), p.899-910
Main Authors: Dobre, Adela F., Mădălan, Augustin M., Hanganu, Anamaria, Ionita, Petre
Format: Article
Language:English
Subjects:
Ascorbic acid
betaine
Betaines
DPPH
Electrons
ESR
free radical
Free radicals
Hydrazines
NMR
Nuclear magnetic resonance
Oxidation
Single crystals
structural characterization
synthesis
Vitamin C
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Summary:Starting from the well known stable free radical DPPH (or its reduced counterpart, 2,2-diphenyl-1-picryl-hydrazine) and several amino derivatives, novel zwitterionic compounds (diazenium betaines) were obtained and characterized by different means, like NMR, IR, MS, and UV–Vis. These betaines are highly intense blue-colored compounds that can be easily reduced by ascorbic acid (vitamin C) or sodium ascorbate to their corresponding para-phenyl substituted derivatives of DPPH, which have a yellow color. Most of such redox processes were found to be reversible. However, the oxidation of 2-p-aminophenyl-2-phenyl-1-picryl-hydrazine led to an azo-derivative of DPPH diradical, and its structure was unveiled by X-ray monocrystal diffraction. Possible diradicaloid behavior is also discussed.
ISSN:2624-8549
2624-8549
DOI:10.3390/chemistry6050052