Carbon–Bromide Bond Activation by Bidentate Halogen, Chalcogen, Pnicogen, and Tetrel Bonds DOI
Yang Xu, Chang Zhao, Cuihong Sun

et al.

The Journal of Physical Chemistry A, Journal Year: 2024, Volume and Issue: unknown

Published: Nov. 25, 2024

Halogen, chalcogen, pnictogen, and tetrel bonds in organocatalysis have gained noticeable attention. In this work, carbon-bromide bond activation the Ritter reaction by bidentate imidazole-type halogen, pnicogen, donors was studied density functional theory. All of above four kinds catalysts exhibited excellent catalytic performance. σ-hole interactions were formed between Br atom reactant donors, which elongated C-Br caused rearrangement electron precomplexes, resulting breaking abstraction. Notably, activity chalcogen is best, followed that halogen bond. Although pnicogen not as good bond, they can still be used effective substitutes for providing more choices noncovalent catalysis. Furthermore, within same group, fifth-period atomic catalyst than fourth-period one donor catalysts.

Language: Английский

Iodonium and Telluronium Triflates Serving as Noncovalent Organocatalysts Provide Catalytic Effect in the Schiff Condensation Due to Different Reasons DOI
Ivan O. Putnin, Alexandra A. Sysoeva, Mikhail V. Il’in

et al.

ChemCatChem, Journal Year: 2024, Volume and Issue: unknown

Published: June 15, 2024

Abstract Sulfonium, selenonium, telluronium triflates, as well chloronium, bromonium, and iodonium triflates have been examined in the model Schiff condensation chalcogen‐ halogen bond donating organocatalysts, respectively. The kinetic data indicated that catalytic effect of salt is provided via decrease enthalpy activation reaction, whereas – unexpectedly caused by value entropy activation. In addition, it was experimentally shown activity sulfonium selenonium salts significantly lower than chloronium bromonium salts, but latter pair species less stable under reaction conditions former pair.

Language: Английский

Citations

4
Halonium and Chalconium Salt-Catalyzed Schiff Condensation: Kinetics and DFT Insights into Organocatalyst Activity Parameters DOI
Alexandra A. Sysoeva, Yana V. Safinskaya, Mikhail V. Il’in

et al.

Organic & Biomolecular Chemistry, Journal Year: 2025, Volume and Issue: unknown

Published: Jan. 1, 2025

Chalconium and halonium salts catalyze Schiff condensation. Kinetic data DFT calculations show that the catalytic activity correlates with maximum electrostatic potential on σ-holes, whereas other factors are less significant.

Language: Английский

Citations

0
Comparative Study of the Catalytic Activity of Hypervalent Halogen(III) and Chalcogen(IV) Salts in the Imine–Isocyanide Coupling DOI
Yana V. Safinskaya, Mikhail V. Il’in

Russian Journal of General Chemistry, Journal Year: 2024, Volume and Issue: 94(10), P. 2632 - 2637

Published: Oct. 1, 2024

Language: Английский

Citations

0
Carbon–Bromide Bond Activation by Bidentate Halogen, Chalcogen, Pnicogen, and Tetrel Bonds DOI
Yang Xu, Chang Zhao, Cuihong Sun

et al.

The Journal of Physical Chemistry A, Journal Year: 2024, Volume and Issue: unknown

Published: Nov. 25, 2024

Halogen, chalcogen, pnictogen, and tetrel bonds in organocatalysis have gained noticeable attention. In this work, carbon-bromide bond activation the Ritter reaction by bidentate imidazole-type halogen, pnicogen, donors was studied density functional theory. All of above four kinds catalysts exhibited excellent catalytic performance. σ-hole interactions were formed between Br atom reactant donors, which elongated C-Br caused rearrangement electron precomplexes, resulting breaking abstraction. Notably, activity chalcogen is best, followed that halogen bond. Although pnicogen not as good bond, they can still be used effective substitutes for providing more choices noncovalent catalysis. Furthermore, within same group, fifth-period atomic catalyst than fourth-period one donor catalysts.

Language: Английский

Citations

0