Study of all stages of the Diels-Alder reaction of cyclopentadiene with 2,3-dicyano-1,4-benzoquinone and monoadducts: Kinetics, thermochemistry, and high pressure effect

被引:3
作者
Kolesnikova, Anastasia O. [1 ]
Kornilov, Dmitry A. [1 ]
Gubaidullin, Aidar T. [2 ]
Kiselev, Vladimir D. [1 ]
机构
[1] Kazan Fed Univ, AM Butlerov Chem Inst, Kremlevskaya Str 18, Kazan 420008, Russia
[2] Russian Acad Sci, AE Arbuzov Inst Organ & Phys Chem, FRC Kazan Sci Ctr, Kazan 420088, Russia
关键词
2; 3-dicyano-1; 4-benzoquinone; cyclopentadiene; Diels-Alder reaction; high pressure effect; kinetics; thermochemistry; ANTITUMOR QUINONES; TETRACYANOETHYLENE; 1,4-BENZOQUINONE; CYCLOADDITION; QUADRICYCLANE; ENTHALPIES;
D O I
10.1002/kin.21350
中图分类号
O64 [物理化学(理论化学)、化学物理学];
学科分类号
070304 ; 081704 ;
摘要
The kinetic parameters and enthalpies of the Diels-Alder reactions between cyclopentadiene and 2,3-dicyano-1,4-benzoquinone leading to the formation of two different monoadducts and bisadduct were determined. The stability of adducts is compared. Monoadduct appears to be thermodynamically more stable than the bisadduct. Comparison with the other Diels-Alder reactions studied previously allows us to conclude that the heat effects upon formation of the considered Diels-Alder adducts are the lowest in comparison with all the studied dienophiles.
引用
收藏
页码:301 / 309
页数:9
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