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

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• 作者：Rafie H. Abu-Eittah ; Walid M. I. Hassan ; W. Zordok
• 关键词：Curtius rearrangement ; cinnamoyl azides ; DFT treatment ; one stage mechanism
• 刊名：Journal of Structural Chemistry
• 出版年：2015
• 出版时间：July 2015
• 年：2015
• 卷：56
• 期：4
• 页码：628-641
• 全文大小：928 KB
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• 作者单位：Rafie H. Abu-Eittah (1)
  Walid M. I. Hassan (1)
  W. Zordok (2)
  
  1. Department of Chemistry, Faculty of Science, University of Cairo, Giza, Egypt
  2. Department of Chemistry, Faculty of Science, University of Zagazig, Zagazig, Egypt
  
• 刊物类别：Chemistry and Materials Science
• 刊物主题：Chemistry
  Inorganic Chemistry
  Physical Chemistry
  Atoms, Molecules, Clusters and Plasmas
  Atomic and Molecular Structure and Spectra
  Solid State Physics and Spectroscopy
  Russian Library of Science
  
• 出版者：Springer New York
• ISSN：1573-8779

文摘

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 π system of the studied molecules; strong opposing dipoles span the whole molecule. Keywords Curtius rearrangement cinnamoyl azides DFT treatment one stage mechanism