N-Substituent effects on the stability of ketenimines

被引：0
|
作者：
Sung, KS [1 ]
机构：
[1] Natl Cheng Kung Univ, Dept Chem, Tainan 70101, Taiwan
来源：
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 2 | 2000年 / 4卷
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D O I：
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中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
A homodesmotic reaction was designed to study N-substituent effects on the stability of ketenimines. A good correlation (SE1=-12.27 chi(BE)+29.81) between N-substituted ketenimine stabilization energies (SE1) and substituent group electronegativity has been found. Both N-substituted and C-beta-substituted ketenimine stabilization energies (SE1 and SE2) have good correlations with Taft's dual-substituent-parameters and modified Swain-Lupton constants. As to N-substituent and C-beta-substituent effects on the stability of ketenimines, sigma-donors stabilize ketenimines while sigma-acceptors destabilize them; pi-acceptors stabilize ketenimines while pi-donors destabilize them.
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收藏
页码：847 / 852
页数：6
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