Synthesis, Characterization and Crystal Structure of (Z)-3-(4-Chlorophenylamino)-1-Phenylbut-2-En-1-One

Abstract

The title compound (Z)-3-(4-chlorophenylamino)-1-phenylbut-2-en-1-one, has been prepared in good yield from the condensation reaction of benzoylacetone and 4-chloroaniline, catalyzed by two drops of formic acid. The compound was characterized by 1H NMR, 13C NMR, IR spectroscopy, mass spectrometry, elemental analysis, thermogravimetric analysis (TGA), differential scanning calorimetry (DSC), and single crystal X-ray diffraction. The compound crystallized in the monoclinic crystal system with space group P21/n, Z = 4, V = 1370.3(7) A3, and unit cell parameters a = 6.4063(19) A, b = 7.085(2) A, c = 30.194(9) A, α = 90°, β = 90.824(5)° and γ = 90°. The crystal structure reveals that the compound exists in the enamino-ketone form and not the enol-imine form. Moreover, TGA/DSC analyses of the title compound was studied, showing two distinct endothermic peaks at temperatures of 134.05 and 302.71 °C, corresponding to melting and boiling points, respectively. The crystal structure reveals that the compound exists in the enamino-ketone form and not the enol-imine form. Moreover, TGA/DSC analyses of the title compound was studied, showing two distinct endothermic peaks at temperatures of 134.05 and 302.71 °C, corresponding to melting and boiling points, respectively .