(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. (https://doi.org/10.3390/M911)

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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.

ORCID iDs

Abonia, Rodrigo, Cabrera, Lorena, Quiroga, Jairo, Insuasty, Braulio, Moreno-Fuquen, Rodolfo and Kennedy, Alan R. ORCID logoORCID: https://orcid.org/0000-0003-3652-6015;
  • Item type:Article
    ID code:58160
    Dates:
    Date
    Event
    15 October 2016
    Published
    10 October 2016
    Accepted
    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:25 May 2023 09:50
    Related URLs:
    URI:https://strathprints.strath.ac.uk/id/eprint/58160
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