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      Permanent link:
      https://www.ias.ac.in/article/fulltext/jcsc/128/02/0235-0245

    • Keywords

       

      N-acylaziridine; hydrolysis; isomerization; DFT calculations.

    • Abstract

       

      The acid isomerization of N-acyl-2,2-dimethylaziridines 1 in concentrated sulfuric acid at room temperature leads to oxazolines 2 but the neutral hydrolysis of 1 in pure water at room temperature leads to amidoalcohols 3. However, the use of aqueous solutions of H2SO4 at different concentrations at room temperature leads to a mixture of oxazolines 2, amidoalcohols 3 and allylamides 4 with yields depending on the acidity of the medium and the nature of the acyl group. A mechanism has been suggested to explain the formation of these three products. DFT calculations employing the Gaussian 09 program with DFT/B3LYP methods and 6-311++G(2d,2p) basis set were carried out which gave the most stable geometry as well as their atomic charge distributions of compounds 1-4.

    • Author Affiliations

       

      Madiha Kamoun Mhiri1 Firas Aboumessaad2 Mohamed Lotfi Efrit1 Youssef Arfaoui3 Néji Besbes2

      1. Laboratoire de Synthèse Organique et Hétérocyclique, Département de Chimie, Faculté des Sciences de Tunis, Université Tunis El Manar, 2092, El Manar, Tunis, Tunisia
      2. Laboratoire Physicochimie de Matériaux Minéraux et leurs Applications, Centre National des Recherches en Sciences des Matériaux, Technopole Borj Cédria, Soliman, 8027, Tunisia
      3. Unité Physico Chimie des Matériaux Condensés -UR11ES19 Département de Chimie Faculté des Sciences de Tunis, Université Tunis El Manar, 2092, El Manar, Tunis, Tunisia

    • Dates

       
      Published
      February 2016
      Manuscript received
      9 July 2015
      Manuscript revised
      2 November 2015
      Accepted
      30 November 2015

    • Supplementary Material

       

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