Iodonium and Telluronium Triflates Serving as Noncovalent Organocatalysts Provide Catalytic Effect in the Schiff Condensation Due to Different Reasons

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Iodonium and Telluronium Triflates Serving as Noncovalent Organocatalysts Provide Catalytic Effect in the Schiff Condensation Due to Different Reasons. / Болотин, Дмитрий Сергеевич ; Путнин, Иван Олегович ; Сысоева, Александра Александровна ; Ильин, Михаил Вячеславович.

In: ChemCatChem, 15.06.2024.

Research output: Contribution to journal › Article › peer-review

BibTeX

@article{e22ec385b42c4f20a078507a65798717,

title = "Iodonium and Telluronium Triflates Serving as Noncovalent Organocatalysts Provide Catalytic Effect in the Schiff Condensation Due to Different Reasons",

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

author = "Болотин, {Дмитрий Сергеевич} and Путнин, {Иван Олегович} and Сысоева, {Александра Александровна} and Ильин, {Михаил Вячеславович}",

year = "2024",

month = jun,

day = "15",

doi = "10.1002/cctc.202400672",

language = "English",

journal = "ChemCatChem",

issn = "1867-3880",

publisher = "Wiley-Blackwell",

}

RIS

TY - JOUR

T1 - Iodonium and Telluronium Triflates Serving as Noncovalent Organocatalysts Provide Catalytic Effect in the Schiff Condensation Due to Different Reasons

AU - Болотин, Дмитрий Сергеевич

AU - Путнин, Иван Олегович

AU - Сысоева, Александра Александровна

AU - Ильин, Михаил Вячеславович

PY - 2024/6/15

Y1 - 2024/6/15

N2 - Sulfonium, selenonium, telluronium triflates, as well as chloronium, bromonium, and iodonium triflates have been examined in the model Schiff condensation as chalcogen‐ and halogen bond donating organocatalysts, respectively. The kinetic data indicated that the catalytic effect of the telluronium salt is provided via the decrease of enthalpy of activation of the reaction, whereas the catalytic effect of the iodonium salt — unexpectedly — is caused by the decrease of the value of the entropy of activation. In addition, it was experimentally shown that the catalytic activity of sulfonium and selenonium is significantly lower than that of chloronium and bromonium salts, but the latter pair of species is significantly less stable under the reaction conditions than the former pair.

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

UR - https://www.mendeley.com/catalogue/7b83ff77-7e12-32a8-9f98-c8a4f167befa/

U2 - 10.1002/cctc.202400672

DO - 10.1002/cctc.202400672

M3 - Article

JO - ChemCatChem

JF - ChemCatChem

SN - 1867-3880

ER -

ID: 120911477