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    • Keywords


      Indolin-2-one; crystallography; DFT-computation; tautomerism

    • Abstract


      The synthesis and spectral characterization of the (𝐸)-3-benzylideneindolin-2-one is reported. The compound crystallized in the monoclinic system with space group P 21/𝑛 with cell coordinates 𝑎 = 3.9849 (2) Å, 𝑏 = 22.2236 (9) Å, 𝑐 = 12.2501 (5) Å, 𝛽 = 95.0535 (12)° , 𝑉 =1080.64 (8) Å 3 , and 𝑍 = 4. In the crystal, molecules are packed in chains formed via weak intermolecular C13–H13A· · · O1 and N1-H1N1. . .O1 hydrogen bonding. The relative stabilities of the two tautomeric isomers of 3 are calculated by DFT/B3LYP method using 6-311G(d,p) basis set in gas phase and in solution. The quantum chemical calculations, NMR studies and the XRD analyses showed that the keto form T0 is the only form that could exist in gas, solution and solid phases respectively. The calculated geometric parameters of the dimer molecule showed better agreement with the XRD data than those obtained for single isolated molecule. This shed light on the effect of intermolecular interactions on the calculated geometric parameters. MEP study showed that, the O-atom and the NH proton are the most reactive H-acceptor and H-donor sites, respectively. The N-H...O H-bonding interactions increased the negative charge at the O-atoms and the positive charge of the NH protons compared to the monomer unit.

    • Author Affiliations


      Assem Barakat1 2 Abdullah Mohammed Al-Majid3 Mohammad Shahidul Islam1 M Ali1 Saied M Soliman3 2 Mohammed Rafiq Hussain Siddiqui1 Hazem A Ghabbour4 Hoong-Kun Fun4 5

      1. Department of Chemistry, College of Science, King Saud University, P. O. Box 2455, Riyadh 11451, Saudi Arabia
      2. Department of Chemistry, Faculty of Science, Alexandria University, P.O. Box 426, Ibrahimia, Alexandria 21321, Egypt
      3. Department of Chemistry, College of Science & Arts, King Abdulaziz University, P.O. Box 344, Rabigh 21911, Saudi Arabia
      4. Department of Pharmaceutical Chemistry, College of Pharmacy, King Saud University, P.O. Box 2457, Riyadh 11451, Saudi Arabia
      5. X-Ray Crystallography Unit, School of Physics, Universiti Sains Malaysia, Penang, 11800 Malaysia
    • Dates

  • Journal of Chemical Sciences | News

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