(E)-1-(2-Aminophenyl)-3-(4-chlorophenyl)prop-2-en-1-one
Abonia, Rodrigo and Cabrera, Lorena and Quiroga, Jairo and Insuasty, Braulio and Moreno-Fuquen, Rodolfo and Kennedy, Alan R. (2016) (E)-1-(2-Aminophenyl)-3-(4-chlorophenyl)prop-2-en-1-one. Molbank, 2016 (4). M911.
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Text (Abonia-etal-Molbank-2016-(E)-1-(2-Aminophenyl)-3-(4-chlorophenyl)prop-2)
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Abstract
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.
Creators(s): |
Abonia, Rodrigo, Cabrera, Lorena, Quiroga, Jairo, Insuasty, Braulio, Moreno-Fuquen, Rodolfo and Kennedy, Alan R. ![]() | Item type: | Article |
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ID code: | 58160 |
Keywords: | o-aminoacetophenones, Claisen–Schmidt condensation, o-aminochalcones, single crystal X-ray diffraction, Chemistry, Chemistry(all) |
Subjects: | Science > Chemistry |
Department: | Faculty of Science > Pure and Applied Chemistry |
Depositing user: | Pure Administrator |
Date deposited: | 14 Oct 2016 14:24 |
Last modified: | 23 Jan 2021 03:25 |
Related URLs: | |
URI: | https://strathprints.strath.ac.uk/id/eprint/58160 |
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