On the Development of Selective Chelators for Cadmium: Synthesis, Structure and Chelating Properties of 3-((5-(trifluoromethyl)-1,3,4-thiadiazol-2-yl)amino)benzo[<i>d</i>]isothiazole 1,1-dioxide, a Novel Thiadiazolyl Saccharinate
Aquatic contamination by heavy metals is a major concern for the serious negative consequences it has for plants, animals, and humans. Among the most toxic metals, Cd(II) stands out since selective and truly efficient methodologies for its removal are not known. We report a novel multidentate chelat...
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| Format: | Article |
| Language: | English |
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MDPI AG
2021-03-01
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| Series: | Molecules |
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| Online Access: | https://www.mdpi.com/1420-3049/26/6/1501 |
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| author | Joana F. Leal Bruno Guerreiro Patrícia S. M. Amado André L. Fernandes Luísa Barreira José A. Paixão Maria L. S. Cristiano |
| author_facet | Joana F. Leal Bruno Guerreiro Patrícia S. M. Amado André L. Fernandes Luísa Barreira José A. Paixão Maria L. S. Cristiano |
| author_sort | Joana F. Leal |
| collection | DOAJ |
| description | Aquatic contamination by heavy metals is a major concern for the serious negative consequences it has for plants, animals, and humans. Among the most toxic metals, Cd(II) stands out since selective and truly efficient methodologies for its removal are not known. We report a novel multidentate chelating agent comprising the heterocycles thiadiazole and benzisothiazole. 3-((5-(trifluoromethyl)-1,3,4-thiadiazol-2-yl)amino)benzo[<i>d</i>]isothiazole 1,1-dioxide (AL14) was synthesized from cheap saccharin and characterized by different techniques, including single crystal X-ray crystallography. Our studies revealed the efficiency and selectivity of AL14 for the chelation of dissolved Cd(II) (as compared to Cu(II) and Fe(II)). Different spectral changes were observed upon the addition of Cd(II) and Cu(II) during UV-Vis titrations, suggesting different complexation interactions with both metals. |
| first_indexed | 2024-03-10T13:23:26Z |
| format | Article |
| id | doaj.art-a7c0d84a6bde4053b786aeaa38417a6e |
| institution | Directory Open Access Journal |
| issn | 1420-3049 |
| language | English |
| last_indexed | 2024-03-10T13:23:26Z |
| publishDate | 2021-03-01 |
| publisher | MDPI AG |
| record_format | Article |
| series | Molecules |
| spelling | doaj.art-a7c0d84a6bde4053b786aeaa38417a6e2023-11-21T09:52:10ZengMDPI AGMolecules1420-30492021-03-01266150110.3390/molecules26061501On the Development of Selective Chelators for Cadmium: Synthesis, Structure and Chelating Properties of 3-((5-(trifluoromethyl)-1,3,4-thiadiazol-2-yl)amino)benzo[<i>d</i>]isothiazole 1,1-dioxide, a Novel Thiadiazolyl SaccharinateJoana F. Leal0Bruno Guerreiro1Patrícia S. M. Amado2André L. Fernandes3Luísa Barreira4José A. Paixão5Maria L. S. Cristiano6Center of Marine Sciences, CCMAR, Gambelas Campus, University of Algarve, UAlg, 8005-139 Faro, PortugalCenter of Marine Sciences, CCMAR, Gambelas Campus, University of Algarve, UAlg, 8005-139 Faro, PortugalCenter of Marine Sciences, CCMAR, Gambelas Campus, University of Algarve, UAlg, 8005-139 Faro, PortugalCenter of Marine Sciences, CCMAR, Gambelas Campus, University of Algarve, UAlg, 8005-139 Faro, PortugalCenter of Marine Sciences, CCMAR, Gambelas Campus, University of Algarve, UAlg, 8005-139 Faro, PortugalCFisUC, Department of Physics, University of Coimbra, 3004-516 Coimbra, PortugalCenter of Marine Sciences, CCMAR, Gambelas Campus, University of Algarve, UAlg, 8005-139 Faro, PortugalAquatic contamination by heavy metals is a major concern for the serious negative consequences it has for plants, animals, and humans. Among the most toxic metals, Cd(II) stands out since selective and truly efficient methodologies for its removal are not known. We report a novel multidentate chelating agent comprising the heterocycles thiadiazole and benzisothiazole. 3-((5-(trifluoromethyl)-1,3,4-thiadiazol-2-yl)amino)benzo[<i>d</i>]isothiazole 1,1-dioxide (AL14) was synthesized from cheap saccharin and characterized by different techniques, including single crystal X-ray crystallography. Our studies revealed the efficiency and selectivity of AL14 for the chelation of dissolved Cd(II) (as compared to Cu(II) and Fe(II)). Different spectral changes were observed upon the addition of Cd(II) and Cu(II) during UV-Vis titrations, suggesting different complexation interactions with both metals.https://www.mdpi.com/1420-3049/26/6/1501cadmium chelationaquatic remediationsaccharin-based ligandsbenzisothiazolesthiadiazolesselectivity |
| spellingShingle | Joana F. Leal Bruno Guerreiro Patrícia S. M. Amado André L. Fernandes Luísa Barreira José A. Paixão Maria L. S. Cristiano On the Development of Selective Chelators for Cadmium: Synthesis, Structure and Chelating Properties of 3-((5-(trifluoromethyl)-1,3,4-thiadiazol-2-yl)amino)benzo[<i>d</i>]isothiazole 1,1-dioxide, a Novel Thiadiazolyl Saccharinate Molecules cadmium chelation aquatic remediation saccharin-based ligands benzisothiazoles thiadiazoles selectivity |
| title | On the Development of Selective Chelators for Cadmium: Synthesis, Structure and Chelating Properties of 3-((5-(trifluoromethyl)-1,3,4-thiadiazol-2-yl)amino)benzo[<i>d</i>]isothiazole 1,1-dioxide, a Novel Thiadiazolyl Saccharinate |
| title_full | On the Development of Selective Chelators for Cadmium: Synthesis, Structure and Chelating Properties of 3-((5-(trifluoromethyl)-1,3,4-thiadiazol-2-yl)amino)benzo[<i>d</i>]isothiazole 1,1-dioxide, a Novel Thiadiazolyl Saccharinate |
| title_fullStr | On the Development of Selective Chelators for Cadmium: Synthesis, Structure and Chelating Properties of 3-((5-(trifluoromethyl)-1,3,4-thiadiazol-2-yl)amino)benzo[<i>d</i>]isothiazole 1,1-dioxide, a Novel Thiadiazolyl Saccharinate |
| title_full_unstemmed | On the Development of Selective Chelators for Cadmium: Synthesis, Structure and Chelating Properties of 3-((5-(trifluoromethyl)-1,3,4-thiadiazol-2-yl)amino)benzo[<i>d</i>]isothiazole 1,1-dioxide, a Novel Thiadiazolyl Saccharinate |
| title_short | On the Development of Selective Chelators for Cadmium: Synthesis, Structure and Chelating Properties of 3-((5-(trifluoromethyl)-1,3,4-thiadiazol-2-yl)amino)benzo[<i>d</i>]isothiazole 1,1-dioxide, a Novel Thiadiazolyl Saccharinate |
| title_sort | on the development of selective chelators for cadmium synthesis structure and chelating properties of 3 5 trifluoromethyl 1 3 4 thiadiazol 2 yl amino benzo i d i isothiazole 1 1 dioxide a novel thiadiazolyl saccharinate |
| topic | cadmium chelation aquatic remediation saccharin-based ligands benzisothiazoles thiadiazoles selectivity |
| url | https://www.mdpi.com/1420-3049/26/6/1501 |
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