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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2024-09-01
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| author | Adela F. Dobre Augustin M. Mădălan Anamaria Hanganu Petre Ionita |
| author_facet | Adela F. Dobre Augustin M. Mădălan Anamaria Hanganu Petre Ionita |
| author_sort | Adela F. Dobre |
| collection | DOAJ |
| description | 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 <i>para</i>-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-<i>p</i>-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. |
| format | Article |
| id | doaj-art-86f81a40521943689b0a28d8fc8cb46e |
| institution | OA Journals |
| issn | 2624-8549 |
| language | English |
| publishDate | 2024-09-01 |
| publisher | MDPI AG |
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| series | Chemistry |
| spelling | doaj-art-86f81a40521943689b0a28d8fc8cb46e2025-08-20T02:10:59ZengMDPI AGChemistry2624-85492024-09-016589991010.3390/chemistry6050052Diazenium Betaines Derived from the Stable Free Radical DPPH with Diradicaloid BehaviorAdela F. Dobre0Augustin M. Mădălan1Anamaria Hanganu2Petre Ionita3Department of Inorganic, Organic, Bioorganic and Catalysis, Faculty of Chemistry, University of Bucharest, Panduri 90, 050663 Bucharest, RomaniaDepartment of Inorganic, Organic, Bioorganic and Catalysis, Faculty of Chemistry, University of Bucharest, Panduri 90, 050663 Bucharest, RomaniaDepartment of Inorganic, Organic, Bioorganic and Catalysis, Faculty of Chemistry, University of Bucharest, Panduri 90, 050663 Bucharest, RomaniaDepartment of Inorganic, Organic, Bioorganic and Catalysis, Faculty of Chemistry, University of Bucharest, Panduri 90, 050663 Bucharest, RomaniaStarting 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 <i>para</i>-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-<i>p</i>-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.https://www.mdpi.com/2624-8549/6/5/52free radicalDPPHbetainesynthesisstructural characterizationESR |
| spellingShingle | Adela F. Dobre Augustin M. Mădălan Anamaria Hanganu Petre Ionita Diazenium Betaines Derived from the Stable Free Radical DPPH with Diradicaloid Behavior Chemistry free radical DPPH betaine synthesis structural characterization ESR |
| title | Diazenium Betaines Derived from the Stable Free Radical DPPH with Diradicaloid Behavior |
| title_full | Diazenium Betaines Derived from the Stable Free Radical DPPH with Diradicaloid Behavior |
| title_fullStr | Diazenium Betaines Derived from the Stable Free Radical DPPH with Diradicaloid Behavior |
| title_full_unstemmed | Diazenium Betaines Derived from the Stable Free Radical DPPH with Diradicaloid Behavior |
| title_short | Diazenium Betaines Derived from the Stable Free Radical DPPH with Diradicaloid Behavior |
| title_sort | diazenium betaines derived from the stable free radical dpph with diradicaloid behavior |
| topic | free radical DPPH betaine synthesis structural characterization ESR |
| url | https://www.mdpi.com/2624-8549/6/5/52 |
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