Kazan (Volga region) Federal University, KFU
KAZAN
FEDERAL UNIVERSITY
 
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
Form of presentationArticles in international journals and collections
Year of publication2021
Языканглийский
  • 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

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