Mechanistic Aspects of [3+2] Cycloaddition Reaction of Trifluoroacetonitrile with Diarylnitrilimines in Light of Molecular Electron Density Theory Quantum Chemical Study
In this study, we investigated the [3+2] cycloaddition reaction of CF<sub>3</sub>CN (TFAN) with nitrilimine (NI) to produce 1,2,4-triazole and compared the resulting isomers. We determined the preferred reaction pathway by examining the electrophilic and nucleophilic properties of the re...
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2024-12-01
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| Series: | Molecules |
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| author | Agnieszka Łapczuk Mar Ríos-Gutiérrez |
| author_facet | Agnieszka Łapczuk Mar Ríos-Gutiérrez |
| author_sort | Agnieszka Łapczuk |
| collection | DOAJ |
| description | In this study, we investigated the [3+2] cycloaddition reaction of CF<sub>3</sub>CN (TFAN) with nitrilimine (NI) to produce 1,2,4-triazole and compared the resulting isomers. We determined the preferred reaction pathway by examining the electrophilic and nucleophilic properties of the reaction substrates, performing thermodynamic calculations for the individual pathways, and comparing them with the experimental results. |
| format | Article |
| id | doaj-art-ddce10509d3b4ae2b332c0732cc074af |
| institution | Kabale University |
| issn | 1420-3049 |
| language | English |
| publishDate | 2024-12-01 |
| publisher | MDPI AG |
| record_format | Article |
| series | Molecules |
| spelling | doaj-art-ddce10509d3b4ae2b332c0732cc074af2025-01-10T13:18:50ZengMDPI AGMolecules1420-30492024-12-013018510.3390/molecules30010085Mechanistic Aspects of [3+2] Cycloaddition Reaction of Trifluoroacetonitrile with Diarylnitrilimines in Light of Molecular Electron Density Theory Quantum Chemical StudyAgnieszka Łapczuk0Mar Ríos-Gutiérrez1Department of Organic Chemistry and Technology, Cracow University of Technology, Warszawska 24, 31-155 Cracow, PolandDepartment of Organic Chemistry, University of Valencia, Dr. Moliner 50, Burjassot, 46100 Valencia, SpainIn this study, we investigated the [3+2] cycloaddition reaction of CF<sub>3</sub>CN (TFAN) with nitrilimine (NI) to produce 1,2,4-triazole and compared the resulting isomers. We determined the preferred reaction pathway by examining the electrophilic and nucleophilic properties of the reaction substrates, performing thermodynamic calculations for the individual pathways, and comparing them with the experimental results.https://www.mdpi.com/1420-3049/30/1/85[3+2] cycloadditionnitriliminereactivitymolecular mechanismmolecular electron density theory1,2,4-triazole |
| spellingShingle | Agnieszka Łapczuk Mar Ríos-Gutiérrez Mechanistic Aspects of [3+2] Cycloaddition Reaction of Trifluoroacetonitrile with Diarylnitrilimines in Light of Molecular Electron Density Theory Quantum Chemical Study Molecules [3+2] cycloaddition nitrilimine reactivity molecular mechanism molecular electron density theory 1,2,4-triazole |
| title | Mechanistic Aspects of [3+2] Cycloaddition Reaction of Trifluoroacetonitrile with Diarylnitrilimines in Light of Molecular Electron Density Theory Quantum Chemical Study |
| title_full | Mechanistic Aspects of [3+2] Cycloaddition Reaction of Trifluoroacetonitrile with Diarylnitrilimines in Light of Molecular Electron Density Theory Quantum Chemical Study |
| title_fullStr | Mechanistic Aspects of [3+2] Cycloaddition Reaction of Trifluoroacetonitrile with Diarylnitrilimines in Light of Molecular Electron Density Theory Quantum Chemical Study |
| title_full_unstemmed | Mechanistic Aspects of [3+2] Cycloaddition Reaction of Trifluoroacetonitrile with Diarylnitrilimines in Light of Molecular Electron Density Theory Quantum Chemical Study |
| title_short | Mechanistic Aspects of [3+2] Cycloaddition Reaction of Trifluoroacetonitrile with Diarylnitrilimines in Light of Molecular Electron Density Theory Quantum Chemical Study |
| title_sort | mechanistic aspects of 3 2 cycloaddition reaction of trifluoroacetonitrile with diarylnitrilimines in light of molecular electron density theory quantum chemical study |
| topic | [3+2] cycloaddition nitrilimine reactivity molecular mechanism molecular electron density theory 1,2,4-triazole |
| url | https://www.mdpi.com/1420-3049/30/1/85 |
| work_keys_str_mv | AT agnieszkałapczuk mechanisticaspectsof32cycloadditionreactionoftrifluoroacetonitrilewithdiarylnitriliminesinlightofmolecularelectrondensitytheoryquantumchemicalstudy AT marriosgutierrez mechanisticaspectsof32cycloadditionreactionoftrifluoroacetonitrilewithdiarylnitriliminesinlightofmolecularelectrondensitytheoryquantumchemicalstudy |