Isolation, Characterization and X-ray Structure Determination of the Schiff Base Ligand: 5-Methyl-2-phenyl-4-[phenyl-(4-phenyl-thiazol-2-ylamino)- methylene]-2,4-dihydro-pyrazol-3-one

  • AS Thakar
  • HB Friedrich
  • KT Joshi
  • GEM Maguire
Keywords: Pyrazolone, thiazole, Schiff base, tautomer, X-ray structure

Abstract

The structure of the amine tautomer of the new Schiff base derived from 4-benzoyl-5-methyl-2-phenyl-2,4-dihydro-pyrazol- 3-one (2) and 4-phenyl-thiazol-2-ylamine (3) was confirmed by means of single crystal X-ray diffraction. The title compound (4) was synthesized and crystals were grown from a mixture of dichloromethane and n-hexane (1:3). Single crystal X-ray diffraction analysis show that the structure is primarily stabilized by strong intramolecular N3–H3A···O1 hydrogen bonds [N3–H3A = 0.883(19) Å, H3A···O1=1.925(18) Å, N3···O1=2.6901(13) Å, with an angle for N3–H3A···O1=144.1(17) °] and this leads to the formation of a pseudo nine-membered hydrogen bonded pattern. Elemental analysis, FTIR andNMRanalyses have been employed to characterize the crystal.

KEYWORDS Pyrazolone, thiazole, Schiff base, tautomer, X-ray structure.

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eISSN: 0379-4350