(3E)-1,1,1-Trichloro-4-methoxy-4-phenylbut-3-en-2-one
(3E)-1,1,1-Trichloro-4-methoxy-4-phenylbut-3-en-2-one
Dokument öffnen (12MB)Datum der Veröffentlichung
09.12.2025Verlag / herausgebende Einrichtung
IUCrVerlagsort
Chester, EnglandMetadaten
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Zitierbarer Link (Handle URI) 
https://hdl.handle.net/20.500.11811/14329
Inhalt
The title compound, C11H9Cl3O2, (common name: β-aryl-β-methoxyvinyl trichloromethylketone) was crystallized from a chloroform solution at room temperature. The asymmetric unit comprises one molecule with all atoms in general positions and the E isomerism about the central vinyl entity could be undoubtedly determined. Weak intramolecular interactions between the ketone and the phenyl groups can be suggested, as two O⋅⋅⋅C distances [2.9154 (17) and 2.9780 (15) Å] are shorter than the van der Waals radii sum for the respective atoms (3.35 Å). As a result of the sp3 C atoms and the C—C single bond between the phenyl ring and the central alkene fragment, the molecule is not planar. In the crystal, the molecules are linked by Cl⋅⋅⋅O weak interactions along the a-axis direction (2.962 Å intermolecular distances, compared to the 3.34 Å for the vdW radius sum) and these contacts were observed over the Hirshfeld surfaces set as dnorm, shape-index and curvedness modes. The Hirshfeld surface analysis mapped over the dnorm property indicates that four major contributions for the crystal cohesion are the H⋅⋅⋅Cl/Cl⋅⋅⋅H (34.2%), H⋅⋅⋅H (22.2%), H⋅⋅⋅C/C⋅⋅⋅H (13.5%) and H⋅⋅⋅O/O⋅⋅⋅H (10.6%) contacts. In addition, quantum-mechanical properties were calculated using the B3LYP/6–31 G(d,p) monomer wavefunctions model. The calculations were performed from a single molecular entity within a radial cluster of symmetry-generated molecules, with the radius set to 3.8 Å, and the total intermolecular energies between the molecular pairs range from −3.5 kJ/mol to −22.4 kJ mol−1. An expanded structure section, set to 3 × 3 × 3 unit cells, was used for the visualization of the energy-framework (only the total energy property was selected and the energy cut-off was set to 10.0 kJ/mol). The synthesis and 1H/13C NMR data of the title compound are already published in the literature [Siqueira et al. (1994). Quim. Nova, 17, 24–26].
Schlagwörter
crystal structure, alkenes isomerism, methoxyvinyl ketone
Klassifikation (DDC)
540 ChemieErschienen in
IUCrData, 2025, volume 10, part 12, x251096, S. 1-6Erstpublikation
https://doi.org/10.1107/S241431462501096XBof de Oliveira, Adriano; Bortoluzzi, Adailton João; Flores, Alex Fabiani Claro: (3E)-1,1,1-Trichloro-4-methoxy-4-phenylbut-3-en-2-one. In: IUCrData. 2025, volume 10, part 12, x251096, 1-6.
Online-Ausgabe in bonndoc: https://hdl.handle.net/20.500.11811/14329
Online-Ausgabe in bonndoc: https://hdl.handle.net/20.500.11811/14329
@article{handle:20.500.11811/14329,
author = {{Adriano Bof de Oliveira} and {Adailton João Bortoluzzi} and {Alex Fabiani Claro Flores}},
title = {(3E)-1,1,1-Trichloro-4-methoxy-4-phenylbut-3-en-2-one},
publisher = {IUCr},
year = 2025,
month = dec,
journal = {IUCrData},
volume = 2025, volume 10,
number = part 12, x251096,
pages = 1--6,
note = {The title compound, C11H9Cl3O2, (common name: β-aryl-β-methoxyvinyl trichloromethylketone) was crystallized from a chloroform solution at room temperature. The asymmetric unit comprises one molecule with all atoms in general positions and the E isomerism about the central vinyl entity could be undoubtedly determined. Weak intramolecular interactions between the ketone and the phenyl groups can be suggested, as two O⋅⋅⋅C distances [2.9154 (17) and 2.9780 (15) Å] are shorter than the van der Waals radii sum for the respective atoms (3.35 Å). As a result of the sp3 C atoms and the C—C single bond between the phenyl ring and the central alkene fragment, the molecule is not planar. In the crystal, the molecules are linked by Cl⋅⋅⋅O weak interactions along the a-axis direction (2.962 Å intermolecular distances, compared to the 3.34 Å for the vdW radius sum) and these contacts were observed over the Hirshfeld surfaces set as dnorm, shape-index and curvedness modes. The Hirshfeld surface analysis mapped over the dnorm property indicates that four major contributions for the crystal cohesion are the H⋅⋅⋅Cl/Cl⋅⋅⋅H (34.2%), H⋅⋅⋅H (22.2%), H⋅⋅⋅C/C⋅⋅⋅H (13.5%) and H⋅⋅⋅O/O⋅⋅⋅H (10.6%) contacts. In addition, quantum-mechanical properties were calculated using the B3LYP/6–31 G(d,p) monomer wavefunctions model. The calculations were performed from a single molecular entity within a radial cluster of symmetry-generated molecules, with the radius set to 3.8 Å, and the total intermolecular energies between the molecular pairs range from −3.5 kJ/mol to −22.4 kJ mol−1. An expanded structure section, set to 3 × 3 × 3 unit cells, was used for the visualization of the energy-framework (only the total energy property was selected and the energy cut-off was set to 10.0 kJ/mol). The synthesis and 1H/13C NMR data of the title compound are already published in the literature [Siqueira et al. (1994). Quim. Nova, 17, 24–26].},
url = {https://hdl.handle.net/20.500.11811/14329}
}
author = {{Adriano Bof de Oliveira} and {Adailton João Bortoluzzi} and {Alex Fabiani Claro Flores}},
title = {(3E)-1,1,1-Trichloro-4-methoxy-4-phenylbut-3-en-2-one},
publisher = {IUCr},
year = 2025,
month = dec,
journal = {IUCrData},
volume = 2025, volume 10,
number = part 12, x251096,
pages = 1--6,
note = {The title compound, C11H9Cl3O2, (common name: β-aryl-β-methoxyvinyl trichloromethylketone) was crystallized from a chloroform solution at room temperature. The asymmetric unit comprises one molecule with all atoms in general positions and the E isomerism about the central vinyl entity could be undoubtedly determined. Weak intramolecular interactions between the ketone and the phenyl groups can be suggested, as two O⋅⋅⋅C distances [2.9154 (17) and 2.9780 (15) Å] are shorter than the van der Waals radii sum for the respective atoms (3.35 Å). As a result of the sp3 C atoms and the C—C single bond between the phenyl ring and the central alkene fragment, the molecule is not planar. In the crystal, the molecules are linked by Cl⋅⋅⋅O weak interactions along the a-axis direction (2.962 Å intermolecular distances, compared to the 3.34 Å for the vdW radius sum) and these contacts were observed over the Hirshfeld surfaces set as dnorm, shape-index and curvedness modes. The Hirshfeld surface analysis mapped over the dnorm property indicates that four major contributions for the crystal cohesion are the H⋅⋅⋅Cl/Cl⋅⋅⋅H (34.2%), H⋅⋅⋅H (22.2%), H⋅⋅⋅C/C⋅⋅⋅H (13.5%) and H⋅⋅⋅O/O⋅⋅⋅H (10.6%) contacts. In addition, quantum-mechanical properties were calculated using the B3LYP/6–31 G(d,p) monomer wavefunctions model. The calculations were performed from a single molecular entity within a radial cluster of symmetry-generated molecules, with the radius set to 3.8 Å, and the total intermolecular energies between the molecular pairs range from −3.5 kJ/mol to −22.4 kJ mol−1. An expanded structure section, set to 3 × 3 × 3 unit cells, was used for the visualization of the energy-framework (only the total energy property was selected and the energy cut-off was set to 10.0 kJ/mol). The synthesis and 1H/13C NMR data of the title compound are already published in the literature [Siqueira et al. (1994). Quim. Nova, 17, 24–26].},
url = {https://hdl.handle.net/20.500.11811/14329}
}
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