(Pre)association as a crucial step for computational prediction and analysis of the catalytic activity of σ-hole donating organocatalysts

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(Pre)association as a crucial step for computational prediction and analysis of the catalytic activity of σ-hole donating organocatalysts. / Полонников, Денис Алексеевич ; Ильин, Михаил Вячеславович ; Сафинская, Яна Валерьевна; Алиярова, Ирина Сергеевна; Новиков, Александр Сергеевич ; Болотин, Дмитрий Сергеевич.

в: Organic Chemistry Frontiers, 22.11.2022.

Результаты исследований: Научные публикации в периодических изданиях › статья › Рецензирование

BibTeX

@article{5217b6a8195940e084a186260a1a6ae1,

title = "(Pre)association as a crucial step for computational prediction and analysis of the catalytic activity of σ-hole donating organocatalysts",

abstract = "Based upon the experimentally obtained kinetic data on iodonium salt catalyzed nucleophilic addition of isocyanide to imine leading to imidazopyridine species, a reliable model for DFT calculations has been suggested. It was shown that preassociation of the catalysts with the reaction species might significantly affect the total energy profile of the reaction obtained by DFT. The associates of the organocatalysts featuring the solvent molecules ligated to its σ-holes should be used as a starting point for calculations. Taking these reaction steps into consideration during the calculations leads to significantly more reliable theoretical results, which can be applied either for prediction of the catalytic activity of yet untested species or for justification of the catalytic paths based upon the experimental kinetic data as well.",

author = "Полонников, {Денис Алексеевич} and Ильин, {Михаил Вячеславович} and Сафинская, {Яна Валерьевна} and Алиярова, {Ирина Сергеевна} and Новиков, {Александр Сергеевич} and Болотин, {Дмитрий Сергеевич}",

note = "Publisher Copyright: {\textcopyright} 2022 The Royal Society of Chemistry.",

year = "2022",

month = nov,

day = "22",

doi = "10.1039/d2qo01648f",

language = "English",

journal = "Organic Chemistry Frontiers",

issn = "2052-4110",

publisher = "Royal Society of Chemistry",

}

RIS

TY - JOUR

T1 - (Pre)association as a crucial step for computational prediction and analysis of the catalytic activity of σ-hole donating organocatalysts

AU - Полонников, Денис Алексеевич

AU - Ильин, Михаил Вячеславович

AU - Сафинская, Яна Валерьевна

AU - Алиярова, Ирина Сергеевна

AU - Новиков, Александр Сергеевич

AU - Болотин, Дмитрий Сергеевич

PY - 2022/11/22

Y1 - 2022/11/22

N2 - Based upon the experimentally obtained kinetic data on iodonium salt catalyzed nucleophilic addition of isocyanide to imine leading to imidazopyridine species, a reliable model for DFT calculations has been suggested. It was shown that preassociation of the catalysts with the reaction species might significantly affect the total energy profile of the reaction obtained by DFT. The associates of the organocatalysts featuring the solvent molecules ligated to its σ-holes should be used as a starting point for calculations. Taking these reaction steps into consideration during the calculations leads to significantly more reliable theoretical results, which can be applied either for prediction of the catalytic activity of yet untested species or for justification of the catalytic paths based upon the experimental kinetic data as well.

AB - Based upon the experimentally obtained kinetic data on iodonium salt catalyzed nucleophilic addition of isocyanide to imine leading to imidazopyridine species, a reliable model for DFT calculations has been suggested. It was shown that preassociation of the catalysts with the reaction species might significantly affect the total energy profile of the reaction obtained by DFT. The associates of the organocatalysts featuring the solvent molecules ligated to its σ-holes should be used as a starting point for calculations. Taking these reaction steps into consideration during the calculations leads to significantly more reliable theoretical results, which can be applied either for prediction of the catalytic activity of yet untested species or for justification of the catalytic paths based upon the experimental kinetic data as well.

UR - https://pubs.rsc.org/en/content/articlelanding/2022/qo/d2qo01648f/unauth

UR - http://www.scopus.com/inward/record.url?scp=85143166726&partnerID=8YFLogxK

UR - https://www.mendeley.com/catalogue/b0f16760-a6c3-3ba4-a7ce-bf29359bbd9b/

U2 - 10.1039/d2qo01648f

DO - 10.1039/d2qo01648f

M3 - Article

JO - Organic Chemistry Frontiers

JF - Organic Chemistry Frontiers

SN - 2052-4110

ER -

ID: 100506545