C—C bond formation in the intramolecular Diels-Alder reaction of triene amides
The mechanism nature of the intramolecular Diels–Alder reaction has been performed; and thus, the changes of C—C bond forming/breaking along IRC are characterized in this study. Conceptual DFT analyses of the most favorable adduct fused/exo shows that the flux electronic will take place from diene t...
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| Format: | Article |
| Language: | English |
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Elsevier
2018-02-01
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| Series: | Heliyon |
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| Online Access: | http://www.sciencedirect.com/science/article/pii/S2405844017321679 |
| _version_ | 1818445111348953088 |
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| author | Abdelilah Benallou Habib El Alaoui El Abdallaoui Hocine Garmes |
| author_facet | Abdelilah Benallou Habib El Alaoui El Abdallaoui Hocine Garmes |
| author_sort | Abdelilah Benallou |
| collection | DOAJ |
| description | The mechanism nature of the intramolecular Diels–Alder reaction has been performed; and thus, the changes of C—C bond forming/breaking along IRC are characterized in this study. Conceptual DFT analyses of the most favorable adduct fused/exo shows that the flux electronic will take place from diene to dienophile moiety. Moreover, ELF topological analysis based on the electron density predicts that C—C bond is formed by the coupling of two pseudoradical centers generated at the most significant atoms of the molecules. However, C2 vs C3, also C1 and C4 interaction comes mainly from the global electron density transfer which takes place along the reaction. Two- stage one-step is the proposed mechanism of this reaction, the first stage aims for the formation of C2—C3 σ bond while the second stage aims for C1—C4 σ bond formation. Interestingly, the observed asynchronicity of this IMDA reaction due principally to the asymmetric reorganization of electron density at the most attractive centers. |
| first_indexed | 2024-12-14T19:26:38Z |
| format | Article |
| id | doaj.art-6981220a8f7441819ee4b7d3b3d8be7c |
| institution | Directory Open Access Journal |
| issn | 2405-8440 |
| language | English |
| last_indexed | 2024-12-14T19:26:38Z |
| publishDate | 2018-02-01 |
| publisher | Elsevier |
| record_format | Article |
| series | Heliyon |
| spelling | doaj.art-6981220a8f7441819ee4b7d3b3d8be7c2022-12-21T22:50:12ZengElsevierHeliyon2405-84402018-02-014210.1016/j.heliyon.2018.e00504C—C bond formation in the intramolecular Diels-Alder reaction of triene amidesAbdelilah Benallou0Habib El Alaoui El Abdallaoui1Hocine Garmes2Team of Chemoinformatics Research and Spectroscopy and Quantum Chemistry, Physical and Chemistry Lab, Faculty of Science, El Jadida, MoroccoTeam of Chemoinformatics Research and Spectroscopy and Quantum Chemistry, Physical and Chemistry Lab, Faculty of Science, El Jadida, MoroccoLaboratory of Bio-organic Chemistry, Department of Chemistry, Faculty of Science, El Jadida, MoroccoThe mechanism nature of the intramolecular Diels–Alder reaction has been performed; and thus, the changes of C—C bond forming/breaking along IRC are characterized in this study. Conceptual DFT analyses of the most favorable adduct fused/exo shows that the flux electronic will take place from diene to dienophile moiety. Moreover, ELF topological analysis based on the electron density predicts that C—C bond is formed by the coupling of two pseudoradical centers generated at the most significant atoms of the molecules. However, C2 vs C3, also C1 and C4 interaction comes mainly from the global electron density transfer which takes place along the reaction. Two- stage one-step is the proposed mechanism of this reaction, the first stage aims for the formation of C2—C3 σ bond while the second stage aims for C1—C4 σ bond formation. Interestingly, the observed asynchronicity of this IMDA reaction due principally to the asymmetric reorganization of electron density at the most attractive centers.http://www.sciencedirect.com/science/article/pii/S2405844017321679Theoretical chemistryPhysical chemistryOrganic chemistry |
| spellingShingle | Abdelilah Benallou Habib El Alaoui El Abdallaoui Hocine Garmes C—C bond formation in the intramolecular Diels-Alder reaction of triene amides Heliyon Theoretical chemistry Physical chemistry Organic chemistry |
| title | C—C bond formation in the intramolecular Diels-Alder reaction of triene amides |
| title_full | C—C bond formation in the intramolecular Diels-Alder reaction of triene amides |
| title_fullStr | C—C bond formation in the intramolecular Diels-Alder reaction of triene amides |
| title_full_unstemmed | C—C bond formation in the intramolecular Diels-Alder reaction of triene amides |
| title_short | C—C bond formation in the intramolecular Diels-Alder reaction of triene amides |
| title_sort | c c bond formation in the intramolecular diels alder reaction of triene amides |
| topic | Theoretical chemistry Physical chemistry Organic chemistry |
| url | http://www.sciencedirect.com/science/article/pii/S2405844017321679 |
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