Unexpected Inhibition of the Knoevenagel Condensation in Methanol by Iodonium Salt Served as Electrophilic Activator

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Unexpected Inhibition of the Knoevenagel Condensation in Methanol by Iodonium Salt Served as Electrophilic Activator. / Сысоева, Александра Александровна.

в: Journal of Physical Organic Chemistry, Том 38, № 3, e70006, 01.03.2025.

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

BibTeX

@article{6a3021876b6a4d51be61b15bc326bfed,

title = "Unexpected Inhibition of the Knoevenagel Condensation in Methanol by Iodonium Salt Served as Electrophilic Activator",

abstract = "Halogen bond donors are recognized as electrophilic catalysts in reactions involving carbonyl compounds. This study describes an unexpected inhibition of the Knoevenagel condensation by the catalyst. To elucidate the intricacies of the inhibition mechanism, the overall reaction order and rate constants were determined using 1H NMR spectroscopy, and further experiments with different nucleophiles were conducted. The findings revealed that the inhibition of the primary reaction is attributed to a substantial acceleration of the side reaction involving aldehyde methanolysis, which hinders the formation of the final alkene product.",

keywords = "chemical kinetics, halogen bond donor, inhibition, reaction rate constant, weak interactions",

author = "Сысоева, {Александра Александровна}",

year = "2025",

month = mar,

day = "1",

doi = "10.1002/poc.70006",

language = "English",

volume = "38",

journal = "Journal of Physical Organic Chemistry",

issn = "0894-3230",

publisher = "Wiley-Blackwell",

number = "3",

}

RIS

TY - JOUR

T1 - Unexpected Inhibition of the Knoevenagel Condensation in Methanol by Iodonium Salt Served as Electrophilic Activator

AU - Сысоева, Александра Александровна

PY - 2025/3/1

Y1 - 2025/3/1

N2 - Halogen bond donors are recognized as electrophilic catalysts in reactions involving carbonyl compounds. This study describes an unexpected inhibition of the Knoevenagel condensation by the catalyst. To elucidate the intricacies of the inhibition mechanism, the overall reaction order and rate constants were determined using 1H NMR spectroscopy, and further experiments with different nucleophiles were conducted. The findings revealed that the inhibition of the primary reaction is attributed to a substantial acceleration of the side reaction involving aldehyde methanolysis, which hinders the formation of the final alkene product.

AB - Halogen bond donors are recognized as electrophilic catalysts in reactions involving carbonyl compounds. This study describes an unexpected inhibition of the Knoevenagel condensation by the catalyst. To elucidate the intricacies of the inhibition mechanism, the overall reaction order and rate constants were determined using 1H NMR spectroscopy, and further experiments with different nucleophiles were conducted. The findings revealed that the inhibition of the primary reaction is attributed to a substantial acceleration of the side reaction involving aldehyde methanolysis, which hinders the formation of the final alkene product.

KW - chemical kinetics

KW - halogen bond donor

KW - inhibition

KW - reaction rate constant

KW - weak interactions

UR - https://www.mendeley.com/catalogue/4473fca5-46a0-3c6d-9222-1d8390b6acf3/

U2 - 10.1002/poc.70006

DO - 10.1002/poc.70006

M3 - Article

VL - 38

JO - Journal of Physical Organic Chemistry

JF - Journal of Physical Organic Chemistry

SN - 0894-3230

IS - 3

M1 - e70006

ER -

ID: 132224213