Synthesis, Characterization and Crystal Structure of (2Z)-3-[(4-Methylphenyl)amino]-1-phenylbut-2-en-1-one

• DOI: 10.1007/s10870-012-0279-8
• Publication Date: 2012-02-11T07:26:28Z
• Authors: Siddappa A. Patil; Diego Gonzalez-Fl...; Phillip A. Medina; Jason K. Vohs; Seth Dever; Joshua Popp; Michael Stentzel; Leslie W. Pineda; Mavis L. Montero; Bradley D. Fahlman
• Keywords: Organometallic Chemistry; Characterization

The compound (2Z)-3-[(4-methylphenyl)amino]-1-phenylbut-2-en-1-one was synthesized by the condensation reaction of benzoylacetone with p-methylaniline and structurally characterized by 1H NMR, 13C NMR, IR, mass spectrometry, elemental analysis, TGA/DSC and single crystal X-ray diffraction. The title compound crystallizes in the orthorhombic space group Pccn (No. 56) with a = 17.0042(18) A, b = 11.5826(13) A, c = 14.0514(15) A, V = 2767.5(5) A3 and Z = 8. Data collection on 223(2) K resulted its structure with R1 = 0.0449, wR2 = 0.0980. The molecules in the unit cell are arranged in layers. The intramolecular hydrogen bonds of the type N–H···O were observed in the structure. The compound exhibits two distinct endothermic peaks at a temperature 94.70 °C and 232.60 °C corresponding to melting and boiling points respectively. The compound (2Z)-3-[(4-methylphenyl)amino]-1-phenylbut-2-en-1-one was synthesized by the condensation reaction of benzoylacetone with p-methylaniline and structurally characterized by 1H NMR, 13C NMR, IR, mass spectrometry, elemental analysis, TGA/DSC and single crystal X-ray diffraction. The title compound crystallizes in the orthorhombic space group Pccn (No. 56) with a = 17.0042(18) A, b = 11.5826(13) A, c = 14.0514(15) A, V = 2767.5(5) A3 and Z = 8. Data collection on 223(2) K resulted its structure with R1 = 0.0449, wR2 = 0.0980.