A theoretical study of the thermal Curtius rearrangement of some cinnamoyl azides using the DFT approach

被引：1
|
作者：
Abu-Eittah, Rafie H. [1 ]
Hassan, Walid M. I. [1 ]
Zordok, W. [2 ]
机构：
[1] Cairo Univ, Dept Chem, Fac Sci, Giza, Egypt
[2] Zagazig Univ, Dept Chem, Fac Sci, Zagazig, Egypt
来源：
JOURNAL OF STRUCTURAL CHEMISTRY | 2015年 / 56卷 / 04期
关键词：
Curtius rearrangement; cinnamoyl azides; DFT treatment; one stage mechanism; ACYL AZIDES; DENSITY; SPECTRA;
D O I：
10.1134/S0022476615040046
中图分类号：
O61 [无机化学];
学科分类号：
070301 ; 081704 ;
摘要：
The thermal Curtius rearrangement of cinnamoyl azide, 1-azido-3-phenylprop-2-ene-1-one, and the reactions of some of its derivatives is studied theoretically using the DFT-B3LYP/6-31G(d,p) approach. The potential energy surface profiles of the rearrangement are calculated. The transition state was located and confirmed. The Curtius rearrangement of the studied compounds is a one-stage, discrete reaction. A weak effect of substitution on the reaction rate is due to the unique, localized pi system of the studied molecules; strong opposing dipoles span the whole molecule.
引用
收藏
页码：628 / 641
页数：14
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