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

Rodrigo Abonia, Lorena Cabrera, Jairo Quiroga, Braulio Insuasty, Rodolfo Moreno-Fuquen, Alan R. Kennedy

Research output: Contribution to journalArticle

2 Citations (Scopus)

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.
LanguageEnglish
Article numberM911
Number of pages6
JournalMolbank
Volume2016
Issue number4
DOIs
Publication statusPublished - 15 Oct 2016

Fingerprint

Chalcone
Hydrogen
Molecules
Hydrogen bonds
Alkaloids
X-Ray Diffraction
hydrogen bonds
molecules
alkaloids
Ethanol
Condensation reactions
Temperature
Evaporation
ethyl alcohol
condensation
Crystal structure
routes
fragments
evaporation
Single crystals

Keywords

  • o-aminoacetophenones
  • Claisen–Schmidt condensation
  • o-aminochalcones
  • single crystal X-ray diffraction

Cite this

Abonia, R., Cabrera, L., Quiroga, J., Insuasty, B., Moreno-Fuquen, R., & Kennedy, A. R. (2016). (E)-1-(2-Aminophenyl)-3-(4-chlorophenyl)prop-2-en-1-one. Molbank, 2016(4), [M911]. https://doi.org/10.3390/M911
Abonia, Rodrigo ; Cabrera, Lorena ; Quiroga, Jairo ; Insuasty, Braulio ; Moreno-Fuquen, Rodolfo ; Kennedy, Alan R. / (E)-1-(2-Aminophenyl)-3-(4-chlorophenyl)prop-2-en-1-one. In: Molbank. 2016 ; Vol. 2016, No. 4.
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Abonia, R, Cabrera, L, Quiroga, J, Insuasty, B, Moreno-Fuquen, R & Kennedy, AR 2016, '(E)-1-(2-Aminophenyl)-3-(4-chlorophenyl)prop-2-en-1-one' Molbank, vol. 2016, no. 4, M911. https://doi.org/10.3390/M911

(E)-1-(2-Aminophenyl)-3-(4-chlorophenyl)prop-2-en-1-one. / Abonia, Rodrigo; Cabrera, Lorena; Quiroga, Jairo; Insuasty, Braulio; Moreno-Fuquen, Rodolfo; Kennedy, Alan R.

In: Molbank, Vol. 2016, No. 4, M911, 15.10.2016.

Research output: Contribution to journalArticle

TY - JOUR

T1 - (E)-1-(2-Aminophenyl)-3-(4-chlorophenyl)prop-2-en-1-one

AU - Abonia, Rodrigo

AU - Cabrera, Lorena

AU - Quiroga, Jairo

AU - Insuasty, Braulio

AU - Moreno-Fuquen, Rodolfo

AU - Kennedy, Alan R.

PY - 2016/10/15

Y1 - 2016/10/15

N2 - 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.

AB - 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.

KW - o-aminoacetophenones

KW - Claisen–Schmidt condensation

KW - o-aminochalcones

KW - single crystal X-ray diffraction

UR - http://www.mdpi.com/journal/molbank

U2 - 10.3390/M911

DO - 10.3390/M911

M3 - Article

VL - 2016

JO - Molbank

T2 - Molbank

JF - Molbank

SN - 1422-8599

IS - 4

M1 - M911

ER -

Abonia R, Cabrera L, Quiroga J, Insuasty B, Moreno-Fuquen R, Kennedy AR. (E)-1-(2-Aminophenyl)-3-(4-chlorophenyl)prop-2-en-1-one. Molbank. 2016 Oct 15;2016(4). M911. https://doi.org/10.3390/M911