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- Title
Synthesis, Characterization and Crystal Structure of ( Z)-3-(4-Chlorophenylamino)-1-Phenylbut-2-En-1-One.
- Authors
Patil, Siddappa; Gonzalez-Flores, Diego; Medina, Phillip; Dever, Seth; Stentzel, Michael; Popp, Joshua; Pineda, Leslie; Montero, Mavis; Ziller, Joseph; Fahlman, Bradley
- 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 H NMR, C 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 P2/ n, Z = 4, V = 1370.3(7) Å, and unit cell parameters a = 6.4063(19) Å, b = 7.085(2) Å, c = 30.194(9) Å, 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. Graphical Abstract: 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 [Figure not available: see fulltext.].
- Subjects
CONDENSATION; CHLOROANILINE; FORMIC acid; NUCLEAR magnetic resonance spectroscopy; BOILING-points
- Publication
Journal of Chemical Crystallography, 2012, Vol 42, Issue 6, p543
- ISSN
1074-1542
- Publication type
Article
- DOI
10.1007/s10870-012-0276-y