Chalcogen Bond Catalysis with Telluronium Cations for Bromination Reaction : Importance of Electrostatic and Polarization Effects
© 2023 Wiley-VCH GmbH..
Recently, chalcogen bond catalysts with telluronium cations have garnered considerable attention in organic reactions. In this work, chalcogen bond catalysis on the bromination reaction of anisole with N-bromosuccinimide (NBS) with the telluronium cationic catalysts has been explored with density functional theory (DFT). The catalytic reaction is divided into two stages: the bromine transfer step and the proton transfer step. Based on the computational results, one can find the rate-determining step is the bromine transfer step. Moreover, the present study elucidates that a stronger chalcogen bond between catalysts and NBS will give better catalytic performance. Additionally, this work also clarified the importance of the electrostatic and polarization effects in the chalcogen bond between the oxygen atom of NBS and the Te atom of the catalyst in this bromination reaction. The electrostatic and polarization effects are significantly influenced by the electron-withdrawing ability of the substitution groups on the catalysts. Moreover, the structure-property relationship between the strength of chalcogen bond, electrostatic effect, polarization effect and catalytic performance are established for the design of more efficient chalcogen bond catalysts.
| Medienart: |
E-Artikel |
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| Erscheinungsjahr: |
2023 |
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| Erschienen: |
2023 |
| Enthalten in: |
Zur Gesamtaufnahme - volume:29 |
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| Enthalten in: |
Chemistry (Weinheim an der Bergstrasse, Germany) - 29(2023), 71 vom: 19. Dez., Seite e202302749 |
| Sprache: |
Englisch |
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| Beteiligte Personen: |
Wang, Yanjiang [VerfasserIn] |
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| Links: |
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| Themen: |
Bromination reaction |
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| Anmerkungen: |
Date Revised 20.12.2023 published: Print-Electronic Citation Status PubMed-not-MEDLINE |
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| doi: |
10.1002/chem.202302749 |
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| funding: |
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| Förderinstitution / Projekttitel: |
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| PPN (Katalog-ID): |
NLM362435405 |
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| 500 | |a Citation Status PubMed-not-MEDLINE | ||
| 520 | |a © 2023 Wiley-VCH GmbH. | ||
| 520 | |a Recently, chalcogen bond catalysts with telluronium cations have garnered considerable attention in organic reactions. In this work, chalcogen bond catalysis on the bromination reaction of anisole with N-bromosuccinimide (NBS) with the telluronium cationic catalysts has been explored with density functional theory (DFT). The catalytic reaction is divided into two stages: the bromine transfer step and the proton transfer step. Based on the computational results, one can find the rate-determining step is the bromine transfer step. Moreover, the present study elucidates that a stronger chalcogen bond between catalysts and NBS will give better catalytic performance. Additionally, this work also clarified the importance of the electrostatic and polarization effects in the chalcogen bond between the oxygen atom of NBS and the Te atom of the catalyst in this bromination reaction. The electrostatic and polarization effects are significantly influenced by the electron-withdrawing ability of the substitution groups on the catalysts. Moreover, the structure-property relationship between the strength of chalcogen bond, electrostatic effect, polarization effect and catalytic performance are established for the design of more efficient chalcogen bond catalysts | ||
| 650 | 4 | |a Journal Article | |
| 650 | 4 | |a bromination reaction | |
| 650 | 4 | |a catalytic performance | |
| 650 | 4 | |a chalcogen bond catalysis | |
| 650 | 4 | |a polarization effect | |
| 650 | 4 | |a structure-property relationship | |
| 650 | 4 | |a telluronium cation | |
| 700 | 1 | |a Zhao, Chang |e verfasserin |4 aut | |
| 700 | 1 | |a Chen, Wen-Kai |e verfasserin |4 aut | |
| 700 | 1 | |a Zeng, Yanli |e verfasserin |4 aut | |
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