Electrochemistry and Antioxidant Activities of Substituted Furanyl Nitrone: The Role of the Nitro Group
This work compares electrochemical and antioxidant data for synthetic furfural‐derived nitrone (LQB‐109), the novel N‐methyl‐nitroaryl‐furanyl‐nitrone (LQB‐569), and the parent aldehyde (5NBFAL). Cyclic voltammograms (CVs) are obtained on a glassy carbon electrode (GCE) in acetonitrile (MeCN) and 0....
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| Format: | Article |
| Language: | English |
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Wiley-VCH
2025-07-01
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| Series: | ChemElectroChem |
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| Online Access: | https://doi.org/10.1002/celc.202500068 |
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| author | Danyelle Cândido Santos Débora de Souza dos Santos Costa Paulo R. R. Costa Ayres Guimarães Dias Messias de Oliveira Silva Taualia Achira Aly Vinícius Del Colle Jadriane Almeida Xavier Marília O. F. Goulart Thaissa Lúcio Silva |
| author_facet | Danyelle Cândido Santos Débora de Souza dos Santos Costa Paulo R. R. Costa Ayres Guimarães Dias Messias de Oliveira Silva Taualia Achira Aly Vinícius Del Colle Jadriane Almeida Xavier Marília O. F. Goulart Thaissa Lúcio Silva |
| author_sort | Danyelle Cândido Santos |
| collection | DOAJ |
| description | This work compares electrochemical and antioxidant data for synthetic furfural‐derived nitrone (LQB‐109), the novel N‐methyl‐nitroaryl‐furanyl‐nitrone (LQB‐569), and the parent aldehyde (5NBFAL). Cyclic voltammograms (CVs) are obtained on a glassy carbon electrode (GCE) in acetonitrile (MeCN) and 0.1 mol L−1 n‐Bu4NPF6 versus Ag|AgCl|Cl−, to evaluate cathodic and anodic behavior and chemical processes. The CVs of LQB‐109 display two irreversible cathodic waves at −2.04 V and − 2.19V, related to a four‐electron reduction to hydroxylamine. Two anodic waves appeared at +1.32 V and +1.53 V. The first electron uptake for LQB‐569 occurs in the nitroaromatic group, followed by reductions to give a more electrophilic nitroso, prone to dimerizing and forming reducible azoxy derivatives, along with nitrone reduction, in a 10‐electron total process. One irreversible anodic wave at +1.45 V appears, related to the nitrone oxidation. The electrochemical oxidation profile can be correlated to antioxidant capacity (AO). The ability to scavenge 2,2‐diphenil‐1‐picrylhydrazyl (DPPH)• radicals (% radical scavenging activity) and reduce ferric complexes (ferric‐reducing antioxidant power) were used to assess. LQB‐569 showed low AO, due to the presence of the electron‐withdrawing group, reflecting the oxidative part of the CVs. |
| format | Article |
| id | doaj-art-3e46de3db39a4e3f86b86a239bd2a378 |
| institution | Kabale University |
| issn | 2196-0216 |
| language | English |
| publishDate | 2025-07-01 |
| publisher | Wiley-VCH |
| record_format | Article |
| series | ChemElectroChem |
| spelling | doaj-art-3e46de3db39a4e3f86b86a239bd2a3782025-08-20T03:31:30ZengWiley-VCHChemElectroChem2196-02162025-07-011213n/an/a10.1002/celc.202500068Electrochemistry and Antioxidant Activities of Substituted Furanyl Nitrone: The Role of the Nitro GroupDanyelle Cândido Santos0Débora de Souza dos Santos Costa1Paulo R. R. Costa2Ayres Guimarães Dias3Messias de Oliveira Silva4Taualia Achira Aly5Vinícius Del Colle6Jadriane Almeida Xavier7Marília O. F. Goulart8Thaissa Lúcio Silva9Instituto de Química e Biotecnologia Universidade Federal de Alagoas Maceió CEP: 57072‐970 Alagoas BrasilLaboratório de Química Bioorgânica Instituto de Pesquisas de Produtos Naturais Walter Mors Centro de Ciências da Saúde Bloco H, Universidade Federal do Rio de Janeiro Rio de Janeiro CEP: 21941‐590 Rio de Janeiro BrasilLaboratório de Química Bioorgânica Instituto de Pesquisas de Produtos Naturais Walter Mors Centro de Ciências da Saúde Bloco H, Universidade Federal do Rio de Janeiro Rio de Janeiro CEP: 21941‐590 Rio de Janeiro BrasilDepartamento de Química Orgânica ‐ DQO Universidade do Estado do Rio de Janeiro Rio de Janeiro BrasilInstituto de Química e Biotecnologia Universidade Federal de Alagoas Maceió CEP: 57072‐970 Alagoas BrasilInstituto de Química e Biotecnologia Universidade Federal de Alagoas Maceió CEP: 57072‐970 Alagoas BrasilDepartamento de Química Instituto Tecnológico de Aeronáutica Sâo José dos Campos São Paulo CEP: 12228‐900 BrasilInstituto de Química e Biotecnologia Universidade Federal de Alagoas Maceió CEP: 57072‐970 Alagoas BrasilInstituto de Química e Biotecnologia Universidade Federal de Alagoas Maceió CEP: 57072‐970 Alagoas BrasilNúcleo de Ciências Exatas ‐ NCEx Universidade Federal de Alagoas Campus de Arapiraca Arapiraca CEP: 57309‐005 Alagoas BrasilThis work compares electrochemical and antioxidant data for synthetic furfural‐derived nitrone (LQB‐109), the novel N‐methyl‐nitroaryl‐furanyl‐nitrone (LQB‐569), and the parent aldehyde (5NBFAL). Cyclic voltammograms (CVs) are obtained on a glassy carbon electrode (GCE) in acetonitrile (MeCN) and 0.1 mol L−1 n‐Bu4NPF6 versus Ag|AgCl|Cl−, to evaluate cathodic and anodic behavior and chemical processes. The CVs of LQB‐109 display two irreversible cathodic waves at −2.04 V and − 2.19V, related to a four‐electron reduction to hydroxylamine. Two anodic waves appeared at +1.32 V and +1.53 V. The first electron uptake for LQB‐569 occurs in the nitroaromatic group, followed by reductions to give a more electrophilic nitroso, prone to dimerizing and forming reducible azoxy derivatives, along with nitrone reduction, in a 10‐electron total process. One irreversible anodic wave at +1.45 V appears, related to the nitrone oxidation. The electrochemical oxidation profile can be correlated to antioxidant capacity (AO). The ability to scavenge 2,2‐diphenil‐1‐picrylhydrazyl (DPPH)• radicals (% radical scavenging activity) and reduce ferric complexes (ferric‐reducing antioxidant power) were used to assess. LQB‐569 showed low AO, due to the presence of the electron‐withdrawing group, reflecting the oxidative part of the CVs.https://doi.org/10.1002/celc.202500068antioxidant assayscyclic voltammetryelectrochemical mechanismhybrid compoundsnitro‐nitrones |
| spellingShingle | Danyelle Cândido Santos Débora de Souza dos Santos Costa Paulo R. R. Costa Ayres Guimarães Dias Messias de Oliveira Silva Taualia Achira Aly Vinícius Del Colle Jadriane Almeida Xavier Marília O. F. Goulart Thaissa Lúcio Silva Electrochemistry and Antioxidant Activities of Substituted Furanyl Nitrone: The Role of the Nitro Group ChemElectroChem antioxidant assays cyclic voltammetry electrochemical mechanism hybrid compounds nitro‐nitrones |
| title | Electrochemistry and Antioxidant Activities of Substituted Furanyl Nitrone: The Role of the Nitro Group |
| title_full | Electrochemistry and Antioxidant Activities of Substituted Furanyl Nitrone: The Role of the Nitro Group |
| title_fullStr | Electrochemistry and Antioxidant Activities of Substituted Furanyl Nitrone: The Role of the Nitro Group |
| title_full_unstemmed | Electrochemistry and Antioxidant Activities of Substituted Furanyl Nitrone: The Role of the Nitro Group |
| title_short | Electrochemistry and Antioxidant Activities of Substituted Furanyl Nitrone: The Role of the Nitro Group |
| title_sort | electrochemistry and antioxidant activities of substituted furanyl nitrone the role of the nitro group |
| topic | antioxidant assays cyclic voltammetry electrochemical mechanism hybrid compounds nitro‐nitrones |
| url | https://doi.org/10.1002/celc.202500068 |
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