Origin and switch of different colors: Thermo-isomerism and crystal structure of (1E,2E)-bis[1-(4-nitrophenyl)ethylidene] hydrazine

Tighadouini S., Radi S., Toupet L., Sirajuddin M., Ben Hadda T., AKKURT M. , ...Daha Fazla

JOURNAL OF CHEMICAL SCIENCES, cilt.127, sa.12, ss.2211-2216, 2015 (SCI İndekslerine Giren Dergi) identifier identifier

  • Yayın Türü: Makale / Tam Makale
  • Cilt numarası: 127 Konu: 12
  • Basım Tarihi: 2015
  • Doi Numarası: 10.1007/s12039-015-0992-x
  • Sayfa Sayıları: ss.2211-2216


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, H-1 and C-13 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) , V = 2963.42(16) (3), 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) , alpha= 71.133(7), beta= 81.281(5), gamma= 74.895(5) (a similar to), V = 746.86(9) (3), 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) (a similar to), respectively. The crystal structures of both compounds are stabilized by weak intramolecular C-H aEuro broken vertical bar N contacts and intermolecular C-H aEuro broken vertical bar O hydrogen bonding interactions. In addition, pi- pi stacking interactions are observed between the same aromatic rings of molecules.