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

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Abstract

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.

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Authors and Affiliations

  1. Department of Chemistry, Faculty of Science, University of Cairo, Giza, Egypt

    Rafie H. Abu-Eittah & Walid M. I. Hassan

  2. Department of Chemistry, Faculty of Science, University of Zagazig, Zagazig, Egypt

    W. Zordok

Authors
  1. Rafie H. Abu-Eittah
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  2. Walid M. I. Hassan
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  3. W. Zordok
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Corresponding author

Correspondence to Rafie H. Abu-Eittah.

Additional information

The text was submitted by the authors in English. Zhurnal Strukturnoi Khimii, Vol. 56, No. 4, pp. 676-688, July-August, 2015. Original article submitted September 26, 2013.

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Abu-Eittah, R.H., Hassan, W.M.I. & Zordok, W. A theoretical study of the thermal Curtius rearrangement of some cinnamoyl azides using the DFT approach. J Struct Chem 56, 628–641 (2015). https://doi.org/10.1134/S0022476615040046

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