Studies on the Regioselective Nucleophilic Aromatic Substitution (SNAr) Reaction of 2-Substituted 3,5-Dichloropyrazines
2013
Scales, Stephanie | Johnson, Sarah | Hu, Qiyue | Do, Quyen-Quyen | Richardson, Paul | Wang, Fen | Braganza, John | Ren, Shijian | Wan, Yadong | Zheng, Baojiang | Faizi, Darius | McAlpine, Indrawan
Differences in regioselectivity were observed during the SNAr reaction of amines with unsymmetrical 3,5-dichloropyrazines. This study revealed that when the 2-position of the pyrazine was occupied with an electron-withdrawing group (EWG), nucleophilic attack occurred preferentially at the 5-position. When the 2-position was substituted with an electron-donating group (EDG), nucleophilic attack occurred preferentially at the 3-position. These results are reported along with a computational rationale for the experimental observations based on the Fukui index at the reacting centers.
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