Form of presentation | Articles in international journals and collections |
Year of publication | 2021 |
Язык | английский |
|
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 ![](https://shelly.kpfu.ru/pdf/picture/arrow_black_right.gif) |
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 |
|