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The Kinetic Solvent Effect on 1,3‐Dipolar Cycloaddition of 2,2,5,5‐Tetramethyl‐3‐imidazoline‐3‐oxide‐1‐oxyl Научная публикация

Журнал ChemPlusChem
ISSN: 2192-6506
Вых. Данные Год: 2022, Том: 87, Номер: 7, Номер статьи : e202200119, Страниц : DOI: 10.1002/cplu.202200119
Ключевые слова 1,3-dipolar cycloaddition; kinetics; nitrone; nitroxide; solvent effect
Авторы Cherkasov Sergey A. 1 , Kaletina Polina M. 1 , Polienko Yuliya F. 1 , Parkhomenko Dmitriy A. 1
Организации
1 N.N. Vorozhtsov Novosibirsk Institute of Organic Chemistry of Siberian Branch of Russian Academy of Sciences

Информация о финансировании (1)

1 Российский Научный Фонд 20-73-00350

Реферат: The use of 2,2,5,5-tetramethyl-3-imidazoline-3-oxide-1-oxyl (1) as a controlling agent in Nitroxide Mediated Polymerization allows for activation of alkoxyamine homolysis by 1,3-dipolar cycloaddition of a vinyl monomer [Edeleva et al. Chem. Commun. 2019, 55, 190–193]. Polymerization can be carried out in a medium with different polarity and hydrogen bonding capacity which affects the rate of 1,3-dipolar cycloaddition reaction. In the present study, the solvent effect on the rate of this reaction was investigated by the electron paramagnetic resonance and density functional theory for the six different dipolarophiles, e. g. styrene, n-butyl acrylate, acrylonitrile, methyl vinyl ketone, maleic anhydride, and N-phenyl maleimide. The rate of 1,3 dipolar cycloaddition of non-polar styrene was found to be slightly dependent on solvent, while one order of magnitude decrease in rate coefficient is observed for other dipolarophiles when going from hexane to methanol.
Библиографическая ссылка: Cherkasov S.A. , Kaletina P.M. , Polienko Y.F. , Parkhomenko D.A.
The Kinetic Solvent Effect on 1,3‐Dipolar Cycloaddition of 2,2,5,5‐Tetramethyl‐3‐imidazoline‐3‐oxide‐1‐oxyl
ChemPlusChem. 2022. V.87. N7. e202200119 . DOI: 10.1002/cplu.202200119 WOS Scopus OpenAlex
Даты:
Поступила в редакцию: 1 апр. 2022 г.
Принята к публикации: 4 июл. 2022 г.
Опубликована в печати: 19 июл. 2022 г.
Опубликована online: 19 июл. 2022 г.
Идентификаторы БД:
Web of science: WOS:000827098900001
Scopus: 2-s2.0-85134556248
OpenAlex: W4283789822
Цитирование в БД:
БД Цитирований
Scopus 1
OpenAlex 1
Web of science 1
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