A computational study of the chemical reactivity of isoxaflutole herbicide and its active metabolite using global and local descriptors
In this work, the chemical reactivity of isoxaflutole (ISOX) and diketonitrile (DKN) was analyzed at the X/6-311++G(2d,2p) (where X = = B3LYP, M06, M06L and ωB97XD) level of theory, in the gas and aqueous phases. The results indicate that DKN, the active metabolite of ISOX, is more stable than isoxa...
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| Format: | Article |
| Language: | English |
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Serbian Chemical Society
2020-01-01
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| Series: | Journal of the Serbian Chemical Society |
| Subjects: | |
| Online Access: | http://www.doiserbia.nb.rs/img/doi/0352-5139/2020/0352-51392000024M.pdf |
| _version_ | 1819058763219337216 |
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| author | Mendoza-Huizar Luis H. Rios-Reyes Clara H. Zuñiga-Trejo Hector |
| author_facet | Mendoza-Huizar Luis H. Rios-Reyes Clara H. Zuñiga-Trejo Hector |
| author_sort | Mendoza-Huizar Luis H. |
| collection | DOAJ |
| description | In this work, the chemical reactivity of isoxaflutole (ISOX) and diketonitrile (DKN) was analyzed at the X/6-311++G(2d,2p) (where X = = B3LYP, M06, M06L and ωB97XD) level of theory, in the gas and aqueous phases. The results indicate that DKN, the active metabolite of ISOX, is more stable than isoxaflutole in both phases. ISOX is susceptible to electrophilic and free radical reactions through the isoxazole ring; while the carbonyl group is attacked by nucleophiles. For DKN nucleophilic and free radical attacks are expected on the aromatic ring, while electrophilic attacks are favored on the oxygen atom of the carbonyl groups. The results suggest that the cleavage of the N–O bond in the isoxazole ring is possible through electrophilic and free radical attacks, while electrophilic and free radical attacks will favor substitutions on the carbonyl groups of DKN. |
| first_indexed | 2024-12-21T14:00:22Z |
| format | Article |
| id | doaj.art-95ec35576df6429a87be31b47b96b2a5 |
| institution | Directory Open Access Journal |
| issn | 0352-5139 1820-7421 |
| language | English |
| last_indexed | 2024-12-21T14:00:22Z |
| publishDate | 2020-01-01 |
| publisher | Serbian Chemical Society |
| record_format | Article |
| series | Journal of the Serbian Chemical Society |
| spelling | doaj.art-95ec35576df6429a87be31b47b96b2a52022-12-21T19:01:23ZengSerbian Chemical SocietyJournal of the Serbian Chemical Society0352-51391820-74212020-01-018591163117410.2298/JSC191105024M0352-51392000024MA computational study of the chemical reactivity of isoxaflutole herbicide and its active metabolite using global and local descriptorsMendoza-Huizar Luis H.0Rios-Reyes Clara H.1Zuñiga-Trejo Hector2Universidad Autónoma del Estado de Hidalgo. Academic Area of Chemistry, Hgo., MéxicoUniversidad La Salle Pachuca. Calle Belisario Domínguez, Centro, Hgo., MéxicoUniversidad Autónoma del Estado de Hidalgo. Academic Area of Chemistry, Hgo., MéxicoIn this work, the chemical reactivity of isoxaflutole (ISOX) and diketonitrile (DKN) was analyzed at the X/6-311++G(2d,2p) (where X = = B3LYP, M06, M06L and ωB97XD) level of theory, in the gas and aqueous phases. The results indicate that DKN, the active metabolite of ISOX, is more stable than isoxaflutole in both phases. ISOX is susceptible to electrophilic and free radical reactions through the isoxazole ring; while the carbonyl group is attacked by nucleophiles. For DKN nucleophilic and free radical attacks are expected on the aromatic ring, while electrophilic attacks are favored on the oxygen atom of the carbonyl groups. The results suggest that the cleavage of the N–O bond in the isoxazole ring is possible through electrophilic and free radical attacks, while electrophilic and free radical attacks will favor substitutions on the carbonyl groups of DKN.http://www.doiserbia.nb.rs/img/doi/0352-5139/2020/0352-51392000024M.pdfisoxaflutolediketonitrilefukui function |
| spellingShingle | Mendoza-Huizar Luis H. Rios-Reyes Clara H. Zuñiga-Trejo Hector A computational study of the chemical reactivity of isoxaflutole herbicide and its active metabolite using global and local descriptors Journal of the Serbian Chemical Society isoxaflutole diketonitrile fukui function |
| title | A computational study of the chemical reactivity of isoxaflutole herbicide and its active metabolite using global and local descriptors |
| title_full | A computational study of the chemical reactivity of isoxaflutole herbicide and its active metabolite using global and local descriptors |
| title_fullStr | A computational study of the chemical reactivity of isoxaflutole herbicide and its active metabolite using global and local descriptors |
| title_full_unstemmed | A computational study of the chemical reactivity of isoxaflutole herbicide and its active metabolite using global and local descriptors |
| title_short | A computational study of the chemical reactivity of isoxaflutole herbicide and its active metabolite using global and local descriptors |
| title_sort | computational study of the chemical reactivity of isoxaflutole herbicide and its active metabolite using global and local descriptors |
| topic | isoxaflutole diketonitrile fukui function |
| url | http://www.doiserbia.nb.rs/img/doi/0352-5139/2020/0352-51392000024M.pdf |
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