Controlling diaza-cope rearrangement reactions with resonance-assisted hydrogen bonds

被引：49

作者：

Chin, J

Mancin, F

Thavarajah, N

Lee, DY

Lough, A

Chung, DS

机构：

[1] Dept Chem, Toronto, ON M5S 3H6, Canada

[2] Dept Chem, Toronto, ON M5S 3H6, Canada

[3] Seoul Natl Univ, Dept Chem, Seoul 151747, South Korea

来源：

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY | 2003年 / 125卷 / 50期

关键词：

METAL COORDINATION; CRYSTAL-STRUCTURE;

D O I：

10.1021/ja0387554

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

NMR studies reveal that the equilibrium between 1 and 2 lies essentially toward 1 to the left without any detectable amount of 2. DFT computation shows that the value of K1 is about 1.4 × 10-5, and X-ray crystal structures show that the resonance-assisted hydrogen bond (RAHB) in 1 (1.66 Å) is shorter than the regular hydrogen bond in 2 (1.75 Å). The enormous selectivity can be explained in terms of the strength of the RAHBs in 1 compared to that of the regular hydrogen bonds in 2. Copyright © 2003 American Chemical Society.

引用

页码：15276 / 15277

页数：2

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