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Computational Study for the Aromatic Nucleophilic Substitution of 4-Dimethylamino-3-Trifluoroacetyl- Quinoline with Various Nucleophiles
Heterocycles ( IF 0.6 ) Pub Date : 2021-02-01 , DOI: 10.3987/com-20-s(k)62 Etsuji Okada , Norio Ota , Souma Nakagawa , Yasuhiro Kamitori
Heterocycles ( IF 0.6 ) Pub Date : 2021-02-01 , DOI: 10.3987/com-20-s(k)62 Etsuji Okada , Norio Ota , Souma Nakagawa , Yasuhiro Kamitori
The aromatic nucleophilic substitutions of 4-dimethylamino- 3-trifluoroacetylquinoline 1 with amines, thiols, and alcohols are elucidated on the basis of DFT calculations. Our calculation results suggest that the reaction of 1 with amines giving N-N exchanged products 4 occurs via Meisenheimer type adducts V whereas the ones with thiols and alcohols proceed via the enol type adducts VII and IX to afford N-S and N-O exchanged products 8 and 9, respectively. It is also clarified that the conditions required for the successful substitution are not controlled by the activation energies on these processes, but by the energy changes on the processes from 1 to each intermediates, V, VII, and IX.
中文翻译:
4-二甲基氨基-3-三氟乙酰基喹啉与各种亲核试剂的芳香亲核取代的计算研究
在DFT计算的基础上,阐明了用胺,硫醇和醇将4-二甲基氨基-3-三氟乙酰基喹啉1进行的芳香亲核取代。我们的计算结果表明,1与胺反应生成NN交换产物4是通过Meisenheimer型加合物V发生的,而与硫醇和醇类的反应则是通过烯醇型加合物VII和IX进行的,从而得到NS和NO交换产物8和9, 分别。还需要说明的是,成功取代所需的条件不受这些过程中活化能的控制,而是受过程中从1到各个中间体V ,VII和IX的能量变化的控制。
更新日期:2021-03-21
中文翻译:
4-二甲基氨基-3-三氟乙酰基喹啉与各种亲核试剂的芳香亲核取代的计算研究
在DFT计算的基础上,阐明了用胺,硫醇和醇将4-二甲基氨基-3-三氟乙酰基喹啉1进行的芳香亲核取代。我们的计算结果表明,1与胺反应生成NN交换产物4是通过Meisenheimer型加合物V发生的,而与硫醇和醇类的反应则是通过烯醇型加合物VII和IX进行的,从而得到NS和NO交换产物8和9, 分别。还需要说明的是,成功取代所需的条件不受这些过程中活化能的控制,而是受过程中从1到各个中间体V ,VII和IX的能量变化的控制。