(E)-1-(2-Aminophenyl)-3-(4-chlorophenyl)prop-2-en-1-one

• Main Authors: Rodrigo Abonia, Lorena Cabrera, Jairo Quiroga, Braulio Insuasty, Rodolfo Moreno-Fuquen, Alan R. Kennedy
• Format: Article
• Language: English
• Published: MDPI AG 2016-10-01
• Series: Molbank
• Subjects: o-aminoacetophenones; Claisen–Schmidt condensation; o-aminochalcones; single crystal X-ray diffraction
• Online Access: http://www.mdpi.com/1422-8599/2016/4/M911

The title chalcone (E)-1-(2-aminophenyl)-3-(4-chlorophenyl)prop-2-en-1-one was prepared with an excellent yield from a Claisen–Schmidt condensation reaction between o-aminoacetophenone and p-chlorobenzaldehyde. This product will be used as a key precursor for the development of an alternative route for the total synthesis of dubamine and graveoline alkaloids. Single crystals of the title compound suitable for X-ray diffraction were grown via slow evaporation in ethanol at room temperature. A complete crystallographic study was performed in depth to unequivocally confirm its structure and determine some interesting supramolecular properties. The crystal structure of the title o-aminochalcone, C15H12ClNO, shows two molecules per asymmetric unit (Z′ = 2) and adopts an E configuration about the C=C double bond. In the title compound, the mean plane of the non-H atoms of the central chalcone fragment C—C(O)—C—C—C is as follows: [r.m.s. deviation = 0.0130 Å for A-B and 0.0043 for C-D molecules]. In the crystal, molecules are linked by N—H...N and C—H...O, hydrogen bonds forming edge-fused R66(46) rings parallel to (100). Additionally, N—H...O hydrogen bonds generate a three-dimensional network.