Next Article in Journal
Benzyl 2-((E)-Tosyliminomethyl)phenylcarbamate
Previous Article in Journal
5-[(3-Fluorophenyl)(2-hydroxy-6-oxocyclohex-1-en-1-yl)methyl]-6-hydroxy-1,3-dimethylpyrimidine-2,4(1H,3H)-dione
Open AccessShort Note

(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
Molbank 2016, 2016(4), M911; https://doi.org/10.3390/M911
Received: 14 September 2016 / Revised: 8 October 2016 / Accepted: 10 October 2016 / Published: 15 October 2016
(This article belongs to the Section Structure Determination)
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
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.

Show more citation formats Show less citations formats
Note that from the first issue of 2016, MDPI journals use article numbers instead of page numbers. See further details here.

Article Access Map by Country/Region

1
Back to TopTop