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Molbank 2016, 2016(4), M911; doi:10.3390/M911

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

1
Department of Chemistry, Universidad del Valle, A.A. 25360, Santiago de Cali, Colombia
2
WestCHEM, Department of Pure and Applied Chemistry, University of Strathclyde, 295 Cathedral Street, Glasgow G1 1XL, Scotland
*
Author to whom correspondence should be addressed.
Academic Editors: René T. Boeré and Norbert Haider
Received: 14 September 2016 / Revised: 8 October 2016 / Accepted: 10 October 2016 / Published: 15 October 2016
(This article belongs to the Section Structure Determination)
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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. View Full-Text
Keywords: o-aminoacetophenones; Claisen–Schmidt condensation; o-aminochalcones; single crystal X-ray diffraction o-aminoacetophenones; Claisen–Schmidt condensation; o-aminochalcones; single crystal X-ray diffraction
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This is an open access article distributed under the Creative Commons Attribution License which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited. (CC BY 4.0).

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MDPI and ACS Style

Abonia, R.; Cabrera, L.; Quiroga, J.; Insuasty, B.; Moreno-Fuquen, R.; Kennedy, A.R. (E)-1-(2-Aminophenyl)-3-(4-chlorophenyl)prop-2-en-1-one. Molbank 2016, 2016, M911.

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