KFU. Card publication. 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

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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

Form of presentation

Articles in international journals and collections

Year of publication

2021

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Authors, employees of KFU

Shulyatev Aleksey Aleksandrovich, author

Bibliographic description in the original language

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

Annotation

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.

Keywords

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

The name of the journal

International Journal of Chemical Kinetics

URL

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

Please use this ID to quote from or refer to the card

https://repository.kpfu.ru/eng/?p_id=271797&p_lang=2

Full metadata record

Field DC	Value	Language
dc.contributor.author	Shulyatev Aleksey Aleksandrovich	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/eng/?p_id=271797&p_lang=2	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	Articles in international journals and collections	ru_RU