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      Permanent link:
      https://www.ias.ac.in/article/fulltext/jcsc/127/12/2211-2216

    • Keywords

       

      Hydrazine derivative; crystal structure; thermo-isomerism; color switching.

    • Abstract

       

      A new symmetric branched 4-nitrophenyl hydrazine compound has been prepared in one-step procedure by direct condensation of aromatic ketone with hydrazine in MeOH. The synthesized compound, red isomer, was characterized by IR, 1H and 13C NMR spectroscopy, Elemental analyses, Mass spectrometry and X-ray crystallography. Refluxing in MeOH solution led to thermo-isomerism offering a white isomer product that was characterized by X-ray crystallography. The red isomer crystallizes in the orthorhombic system having space group Pbcn, with a = 12.7612(4), b = 11.5197(3), c = 20.1586(7) Å, V = 2963.42(16)Å3, Z = 8 while the white isomer crystallizes in the triclinic system having space group P−1, with a = 7.8007(4), 8.5966(7), 12.224 (1) Å, 𝛼 = 71.133(7), 𝛽 = 81.281(5), 𝛾 = 74.895(5)°, V = 746.86(9)Å3, Z = 2. Molecules of both compounds are twisted at N2–N3 bond with the C7-N2-N3-C9 torsion angle of 155.23(12) and −113.36(18)°, respectively. The crystal structures of both compounds are stabilized by weak intramolecular C—H. . .N contacts and intermolecular C—H. . .O hydrogen bonding interactions. In addition, 𝜋–𝜋 stacking interactions are observed between the same aromatic rings of molecules.

    • Author Affiliations

       

      Said Tighadouini1 Smaail Radi1 Loic Toupet2 Muhammad Sirajuddin3 Taibi Ben Hadda4 Mehmet Akkurt5 Ismail Warad6 Yahia N Mabkhot7 Saqib Ali8

      1. LCAE, Département de Chimie, Faculté des Sciences, Université Mohammed Premier, Oujda 60000, Morocco
      2. Institut de Physique de Rennes, UMR 625, Université de Rennes 1, Campus de Beaulieu Bat. 11 A, 263 av. Général Leclerc, 35042 Rennes Cedex, France
      3. Department of Chemistry, University of Science & Technology, Bannu, Pakistan
      4. Laboratoire de Chimie des Matériaux, Faculté des Sciences, Université Mohammed Premier, Oujda 60000, Morocco
      5. Department of Physics, Faculty of Sciences, Erciyes University, 38039 Kayseri, Turkey
      6. Department of Chemistry, An-Najah National University, Nablus, Palestinian Territories
      7. Department of Chemistry, College of Science, King Saud University, P.O. Box 2455, Riyadh 1451, Saudi Arabia
      8. Department of Chemistry, Quaid-i-Azam University, Islamabad, 45320, Pakistan

    • Dates

       
      Published
      December 2015
      Manuscript received
      9 February 2015
      Manuscript revised
      12 August 2015
      Accepted
      22 September 2015

    • Supplementary Material

       

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