Theoretical Analysis of the Mechanism of the 1,3-Dipolar Cycloaddition of Benzodiazepine with N-Aryl-C-ethoxycarbonylnitrilimine
In this work, the mechanism and regio- and no-periselectivity of the 1,3-dipolar cycloaddition reaction of 2,4-dimethyl-3H-1,5-benzodiazepine with N-aryl-C-ethoxycarbonylnitrilimine have been studied using the DFT method at the B3LYP/6-31G(d) level of theory. IRC calculations and activation energies...
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| Format: | Article |
| Language: | English |
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Wiley
2020-01-01
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| Series: | Journal of Chemistry |
| Online Access: | http://dx.doi.org/10.1155/2020/8695405 |
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| author | Khadija Nabih Mohamed Maatallah Abdesselam Baouid Abdellah Jarid |
| author_facet | Khadija Nabih Mohamed Maatallah Abdesselam Baouid Abdellah Jarid |
| author_sort | Khadija Nabih |
| collection | DOAJ |
| description | In this work, the mechanism and regio- and no-periselectivity of the 1,3-dipolar cycloaddition reaction of 2,4-dimethyl-3H-1,5-benzodiazepine with N-aryl-C-ethoxycarbonylnitrilimine have been studied using the DFT method at the B3LYP/6-31G(d) level of theory. IRC calculations and activation energies show that this reaction follows an asynchronous concerted mechanism. The two C=N sites of 2,4-dimethyl-3H-1,5-benzodiazepine are easily reached by the dipole, and the energy barrier between the reagents and the transition states is too weak. The secondary barriers are traversed by the heat released in the reaction medium after the crossing of the first TS, which facilitates the addition reaction and does not require high energy. The obtained results of this study are in good agreement with experimental outcomes. |
| format | Article |
| id | doaj-art-2cc27d488fa44a8485268ec109412796 |
| institution | Kabale University |
| issn | 2090-9063 2090-9071 |
| language | English |
| publishDate | 2020-01-01 |
| publisher | Wiley |
| record_format | Article |
| series | Journal of Chemistry |
| spelling | doaj-art-2cc27d488fa44a8485268ec1094127962025-02-03T01:05:17ZengWileyJournal of Chemistry2090-90632090-90712020-01-01202010.1155/2020/86954058695405Theoretical Analysis of the Mechanism of the 1,3-Dipolar Cycloaddition of Benzodiazepine with N-Aryl-C-ethoxycarbonylnitrilimineKhadija Nabih0Mohamed Maatallah1Abdesselam Baouid2Abdellah Jarid3Laboratory of Molecular Chemistry, Department of Chemistry, Faculty of Sciences Semlalia, University of Cadi Ayyad, BP. 2390, Av. My Abdellah, Marrakech 40000, MoroccoLaboratory of Molecular Chemistry, Department of Chemistry, Faculty of Sciences Semlalia, University of Cadi Ayyad, BP. 2390, Av. My Abdellah, Marrakech 40000, MoroccoLaboratory of Molecular Chemistry, Department of Chemistry, Faculty of Sciences Semlalia, University of Cadi Ayyad, BP. 2390, Av. My Abdellah, Marrakech 40000, MoroccoLaboratory of Molecular Chemistry, Department of Chemistry, Faculty of Sciences Semlalia, University of Cadi Ayyad, BP. 2390, Av. My Abdellah, Marrakech 40000, MoroccoIn this work, the mechanism and regio- and no-periselectivity of the 1,3-dipolar cycloaddition reaction of 2,4-dimethyl-3H-1,5-benzodiazepine with N-aryl-C-ethoxycarbonylnitrilimine have been studied using the DFT method at the B3LYP/6-31G(d) level of theory. IRC calculations and activation energies show that this reaction follows an asynchronous concerted mechanism. The two C=N sites of 2,4-dimethyl-3H-1,5-benzodiazepine are easily reached by the dipole, and the energy barrier between the reagents and the transition states is too weak. The secondary barriers are traversed by the heat released in the reaction medium after the crossing of the first TS, which facilitates the addition reaction and does not require high energy. The obtained results of this study are in good agreement with experimental outcomes.http://dx.doi.org/10.1155/2020/8695405 |
| spellingShingle | Khadija Nabih Mohamed Maatallah Abdesselam Baouid Abdellah Jarid Theoretical Analysis of the Mechanism of the 1,3-Dipolar Cycloaddition of Benzodiazepine with N-Aryl-C-ethoxycarbonylnitrilimine Journal of Chemistry |
| title | Theoretical Analysis of the Mechanism of the 1,3-Dipolar Cycloaddition of Benzodiazepine with N-Aryl-C-ethoxycarbonylnitrilimine |
| title_full | Theoretical Analysis of the Mechanism of the 1,3-Dipolar Cycloaddition of Benzodiazepine with N-Aryl-C-ethoxycarbonylnitrilimine |
| title_fullStr | Theoretical Analysis of the Mechanism of the 1,3-Dipolar Cycloaddition of Benzodiazepine with N-Aryl-C-ethoxycarbonylnitrilimine |
| title_full_unstemmed | Theoretical Analysis of the Mechanism of the 1,3-Dipolar Cycloaddition of Benzodiazepine with N-Aryl-C-ethoxycarbonylnitrilimine |
| title_short | Theoretical Analysis of the Mechanism of the 1,3-Dipolar Cycloaddition of Benzodiazepine with N-Aryl-C-ethoxycarbonylnitrilimine |
| title_sort | theoretical analysis of the mechanism of the 1 3 dipolar cycloaddition of benzodiazepine with n aryl c ethoxycarbonylnitrilimine |
| url | http://dx.doi.org/10.1155/2020/8695405 |
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