Theoretical investigation of Banert cascade reaction
Computational inside of Banert cascade reaction for triazole formation is studied with B3LYP/6-31G(d,p) level of theory. The reaction proceeds mainly by SN2 initial chloride displacement rather than SN2′-type attack. Furthermore, according to the rate of reaction calculation, SN2 displacement is muc...
| Main Authors: | , |
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| Format: | Article |
| Language: | English |
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The Royal Society
2018-01-01
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| Series: | Royal Society Open Science |
| Subjects: | |
| Online Access: | https://royalsocietypublishing.org/doi/pdf/10.1098/rsos.171075 |
| _version_ | 1818134669468631040 |
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| author | S. Bhattacharyya K. Hatua |
| author_facet | S. Bhattacharyya K. Hatua |
| author_sort | S. Bhattacharyya |
| collection | DOAJ |
| description | Computational inside of Banert cascade reaction for triazole formation is studied with B3LYP/6-31G(d,p) level of theory. The reaction proceeds mainly by SN2 initial chloride displacement rather than SN2′-type attack. Furthermore, according to the rate of reaction calculation, SN2 displacement is much faster than SN2′ displacement in the order of 8. The [3,3]-sigmatropic rearrangement for the conversion of propargyl azide into triazafulvene has been proved as the rate-determining step having highest activation energy parameter. Solvent effect on total course of reaction has been found negligible. Furthermore, effects of different density functional theory functionals and functional groups on activation energies of [3,3]-sigmatropic rearrangement of propargyl azide were also studied. BHHLYP, ωB97XD, M062X and BMK calculated ΔG‡ are consistent with B3LYP. |
| first_indexed | 2024-12-11T09:12:18Z |
| format | Article |
| id | doaj.art-4a92ae08ba2a4b359c0a7b1551d3632a |
| institution | Directory Open Access Journal |
| issn | 2054-5703 |
| language | English |
| last_indexed | 2024-12-11T09:12:18Z |
| publishDate | 2018-01-01 |
| publisher | The Royal Society |
| record_format | Article |
| series | Royal Society Open Science |
| spelling | doaj.art-4a92ae08ba2a4b359c0a7b1551d3632a2022-12-22T01:13:27ZengThe Royal SocietyRoyal Society Open Science2054-57032018-01-015410.1098/rsos.171075171075Theoretical investigation of Banert cascade reactionS. BhattacharyyaK. HatuaComputational inside of Banert cascade reaction for triazole formation is studied with B3LYP/6-31G(d,p) level of theory. The reaction proceeds mainly by SN2 initial chloride displacement rather than SN2′-type attack. Furthermore, according to the rate of reaction calculation, SN2 displacement is much faster than SN2′ displacement in the order of 8. The [3,3]-sigmatropic rearrangement for the conversion of propargyl azide into triazafulvene has been proved as the rate-determining step having highest activation energy parameter. Solvent effect on total course of reaction has been found negligible. Furthermore, effects of different density functional theory functionals and functional groups on activation energies of [3,3]-sigmatropic rearrangement of propargyl azide were also studied. BHHLYP, ωB97XD, M062X and BMK calculated ΔG‡ are consistent with B3LYP.https://royalsocietypublishing.org/doi/pdf/10.1098/rsos.171075triazolebanert cascadepropargyl chloridedensity functional theorypropargyl azide |
| spellingShingle | S. Bhattacharyya K. Hatua Theoretical investigation of Banert cascade reaction Royal Society Open Science triazole banert cascade propargyl chloride density functional theory propargyl azide |
| title | Theoretical investigation of Banert cascade reaction |
| title_full | Theoretical investigation of Banert cascade reaction |
| title_fullStr | Theoretical investigation of Banert cascade reaction |
| title_full_unstemmed | Theoretical investigation of Banert cascade reaction |
| title_short | Theoretical investigation of Banert cascade reaction |
| title_sort | theoretical investigation of banert cascade reaction |
| topic | triazole banert cascade propargyl chloride density functional theory propargyl azide |
| url | https://royalsocietypublishing.org/doi/pdf/10.1098/rsos.171075 |
| work_keys_str_mv | AT sbhattacharyya theoreticalinvestigationofbanertcascadereaction AT khatua theoreticalinvestigationofbanertcascadereaction |