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A Two-Step Protocol for Umpolung Functionalization of Ketones Via Enolonium Species
Published on: August 16, 2018
1-(4-Fluoro-phen-yl)-2-(phenyl-sulfon-yl)ethanone
Summary
This study details the crystal structure of a fluorinated ethanone compound. Molecular structure and intermolecular hydrogen bonding interactions were analyzed, revealing specific C-H⋯O bonds that link molecules into dimers.
Area of Science:
- Crystallography
- Organic Chemistry
- Supramolecular Chemistry
Background:
- Understanding the three-dimensional arrangement of atoms in organic molecules is crucial for predicting their properties and reactivity.
- Intermolecular forces, such as hydrogen bonds, play a significant role in the assembly of crystal structures and influence bulk material properties.
Purpose of the Study:
- To elucidate the crystal structure of the title compound, C(14)H(11)FO(3)S.
- To analyze the molecular geometry, including planarity and dihedral angles between key functional groups.
- To investigate the intermolecular interactions, specifically hydrogen bonding, that govern crystal packing.
Main Methods:
- Single-crystal X-ray diffraction was employed to determine the precise atomic coordinates and unit cell parameters.
- Analysis of the crystal structure involved calculating root-mean-square deviations for planar groups and determining dihedral angles.
- Supramolecular analysis was performed to identify and characterize hydrogen bonding networks using graph-set notation.
Main Results:
- The ethanone and 4-fluorophenyl moieties exhibit near planarity, with a root-mean-square deviation of 0.0084(2) Å for non-hydrogen atoms.
- A dihedral angle of 37.31(10)° was observed between the planar unit and the phenyl ring.
- Molecules self-assemble into inversion dimers via weak C-H⋯O hydrogen bonds, forming R(2)(2)(16) motifs.
- These dimers are further organized along the crystallographic b-axis through additional C-H⋯O hydrogen bonds.
Conclusions:
- The crystal structure of C(14)H(11)FO(3)S is characterized by specific molecular conformations and a well-defined hydrogen bonding network.
- The identified C-H⋯O hydrogen bonds are key to the formation of dimers and the overall packing arrangement in the crystal lattice.
- This structural information provides a foundation for understanding the solid-state behavior and potential applications of this fluorinated organic compound.
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