dc.contributor.author |
Kiselev V.D. |
|
dc.contributor.author |
Kolesnikova A.O. |
|
dc.contributor.author |
Shulyatiev A.A. |
|
dc.contributor.author |
Dinikaev I.F. |
|
dc.contributor.author |
Kornilov D.A. |
|
dc.date.accessioned |
2022-02-09T20:34:04Z |
|
dc.date.available |
2022-02-09T20:34:04Z |
|
dc.date.issued |
2021 |
|
dc.identifier.issn |
0538-8066 |
|
dc.identifier.uri |
https://dspace.kpfu.ru/xmlui/handle/net/169070 |
|
dc.description.abstract |
This 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. |
|
dc.relation.ispartofseries |
International Journal of Chemical Kinetics |
|
dc.subject |
2 |
|
dc.subject |
3-dicarboxylic acid |
|
dc.subject |
3-dicyano-p-benzoquinone |
|
dc.subject |
4-benzoquinone-2 |
|
dc.subject |
Diels–Alder reaction |
|
dc.subject |
N-phenylimide-1 |
|
dc.subject |
rate constant |
|
dc.subject |
reaction enthalpy |
|
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 |
|
dc.type |
Article |
|
dc.relation.ispartofseries-issue |
12 |
|
dc.relation.ispartofseries-volume |
53 |
|
dc.collection |
Публикации сотрудников КФУ |
|
dc.relation.startpage |
1306 |
|
dc.source.id |
SCOPUS05388066-2021-53-12-SID85113732641 |
|