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Towards redox-switchable organocatalysts based on bidentate halogen bond donors

Engelage, E ; Hijazi, H ; Gartmann, M ; Chamoreau, L.-M ; Schöllhorn, B ; Huber, S. M ; Fave, C

Physical chemistry chemical physics : PCCP, 2021-02, Vol.23 (7), p.4344-4352 [Periódico revisado por pares]

England: Royal Society of Chemistry

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  • Título:
    Towards redox-switchable organocatalysts based on bidentate halogen bond donors
  • Autor: Engelage, E ; Hijazi, H ; Gartmann, M ; Chamoreau, L.-M ; Schöllhorn, B ; Huber, S. M ; Fave, C
  • Assuntos: Analytical chemistry ; Binding ; Catalysis ; Chemical Sciences ; Coordination chemistry ; Donors (electronic) ; Halides ; Inorganic chemistry ; NMR ; Nuclear magnetic resonance ; or physical chemistry ; Organic chemistry ; Theoretical and
  • É parte de: Physical chemistry chemical physics : PCCP, 2021-02, Vol.23 (7), p.4344-4352
  • Notas: Electronic supplementary information (ESI) available. See DOI
    10.1039/d0cp06612e
    ObjectType-Article-1
    SourceType-Scholarly Journals-1
    ObjectType-Feature-2
    content type line 23
  • Descrição: Redox-active bidentate halogen bond donors based on halopyridinium groups as halogen-bond donating units were synthesized and their structures were elucidated by X-ray diffraction analyses and DFT calculations. Via reversible twofold reduction, these dicationic species can be transformed to neutral compounds which should be much weaker Lewis acids. The corresponding electrochemical data were obtained, and CV as well as UV-vis and NMR techniques were also used to determine binding constants of these halogen bond donors to halides. While all titrations agree on the relative order of binding strengths (with chloride being bound strongest), there are marked deviations in the overall affinity constants which are discussed. In contrast to earlier azo-bridge analogues, the ethylene-linked variants presented herein do not oxidize halides, and thus the novel halogen bond donors could also be used as Lewis acidic organocatalysts in a halide abstraction benchmark reaction, yielding a performance similar to bis(haloimidazolium)-derived catalysts. Novel redox-switchable halogen bond donors were synthesized. Thermodynamic affinity constants towards anions have been determined by electrochemical and spectroscopic techniques. The compounds were successfully employed as effective organocatalysts.
  • Editor: England: Royal Society of Chemistry
  • Idioma: Inglês
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