КФУ. Карточка публикации. Sharp difference in the rate of formation and stability of the Diels–Alder reaction adducts with 2,3-dicyano-1,4-benzoquinone and N-phenylimide-1,4-benzoquinone-2,3-dicarboxylic acid

RUS

- EN
- 中文
- ES

SHARP DIFFERENCE IN THE RATE OF FORMATION AND STABILITY OF THE DIELS&NDASH;ALDER REACTION ADDUCTS WITH 2,3-DICYANO-1,4-BENZOQUINONE AND N-PHENYLIMIDE-1,4-BENZOQUINONE-2,3-DICARBOXYLIC ACID

Форма представления

Статьи в зарубежных журналах и сборниках

Год публикации

2021

Язык

английский

Авторы, сотрудники КФУ

Шулятьев Алексей Александрович, автор

Библиографическое описание на языке оригинала

Kiselev VD, Kolesnikova AO, Shulyatiev AA, DinikaevI F, Kornilov DA. Sharp difference in the rate of formation and stability of the Diels-Alder reaction adducts with 2,3-dicyano-1,4-benzoquinone and N-phenylimide-1,4-benzoquinone-2,3-dicarboxylicacid. Int J Chem Kinet. 2021; 53: 1306–1313. https://doi.org/10.1002/kin.21534

Аннотация

his work reports new studies of the activity and Diels–Alder kinetics of a series of dienophiles: tetracyanoethylene (1), 2,3-dicyano-p-benzoquinone (10), and N-phenylimide-1,4-benzoquinone-2,3-dicarboxylic acid (11). Rate differences are interpreted in terms of the donor–acceptor properties of the reagents. The relative π-acceptor properties of the dienophiles are probed by measuring their interaction energies with a series π-donor solvents: benzene, toluene, o-xylene, and chlorobenzene. The normalized interaction energies of 1, 10, and 11 are found to be 100:64:28. Despite the increased energy of the donor–acceptor interaction, dienophile 10 is 255 times less active in the reaction with 9,10-dimethylanthracene than 11. It is suggested that this is due to the significantly lower energy of π-bond cleavage in bicyclic dienophile 11, compared with monocyclic 10.

Ключевые слова

2,3-dicarboxylic acid, 3-dicyano-p-benzoquinone, 4-benzoquinone-2, Diels?Alder reaction, N-phenylimide-1, rate constant, reaction enthalpy

Название журнала

International Journal of Chemical Kinetics

URL

https://onlinelibrary.wiley.com/doi/epdf/10.1002/kin.21534

Пожалуйста, используйте этот идентификатор, чтобы цитировать или ссылаться на эту карточку

https://repository.kpfu.ru/?p_id=271797

Полная запись метаданных

Поле DC	Значение	Язык
dc.contributor.author	Шулятьев Алексей Александрович	ru_RU
dc.date.accessioned	2021-01-01T00:00:00Z	ru_RU
dc.date.available	2021-01-01T00:00:00Z	ru_RU
dc.date.issued	2021	ru_RU
dc.identifier.citation	Kiselev VD, Kolesnikova AO, Shulyatiev AA, DinikaevI F, Kornilov DA. Sharp difference in the rate of formation and stability of the Diels-Alder reaction adducts with 2,3-dicyano-1,4-benzoquinone and N-phenylimide-1,4-benzoquinone-2,3-dicarboxylicacid. Int J Chem Kinet. 2021; 53: 1306–1313. https://doi.org/10.1002/kin.21534	ru_RU
dc.identifier.uri	https://repository.kpfu.ru/?p_id=271797	ru_RU
dc.description.abstract	International Journal of Chemical Kinetics	ru_RU
dc.description.abstract	his work reports new studies of the activity and Diels–Alder kinetics of a series of dienophiles: tetracyanoethylene (1), 2,3-dicyano-p-benzoquinone (10), and N-phenylimide-1,4-benzoquinone-2,3-dicarboxylic acid (11). Rate differences are interpreted in terms of the donor–acceptor properties of the reagents. The relative π-acceptor properties of the dienophiles are probed by measuring their interaction energies with a series π-donor solvents: benzene, toluene, o-xylene, and chlorobenzene. The normalized interaction energies of 1, 10, and 11 are found to be 100:64:28. Despite the increased energy of the donor–acceptor interaction, dienophile 10 is 255 times less active in the reaction with 9,10-dimethylanthracene than 11. It is suggested that this is due to the significantly lower energy of π-bond cleavage in bicyclic dienophile 11, compared with monocyclic 10.	ru_RU
dc.language.iso	ru	ru_RU
dc.subject	2	ru_RU
dc.subject	3-dicarboxylic acid	ru_RU
dc.subject	3-dicyano-p-benzoquinone	ru_RU
dc.subject	4-benzoquinone-2	ru_RU
dc.subject	Diels?Alder reaction	ru_RU
dc.subject	N-phenylimide-1	ru_RU
dc.subject	rate constant	ru_RU
dc.subject	reaction enthalpy	ru_RU
dc.title	Sharp difference in the rate of formation and stability of the Diels–Alder reaction adducts with 2,3-dicyano-1,4-benzoquinone and N-phenylimide-1,4-benzoquinone-2,3-dicarboxylic acid	ru_RU
dc.type	Статьи в зарубежных журналах и сборниках	ru_RU