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Updated: Jun 1, 2026

Retropinacol/Cross-pinacol Coupling Reactions - A Catalytic Access to 1,2-Unsymmetrical Diols
Published on: April 4, 2014
1,3,5-Tri-p-tolyl-pentane-1,5-dione
1Jiangxi Key Laboratory of Surface Engineering, Jiangxi Science and Technology Normal University, Jiangxi 330013, People's Republic of China.
The crystal structure of C(26)H(26)O(2) reveals specific dihedral angles between tolyl rings in the 1,5-dione chain. These molecules form chains through C-H⋯O hydrogen bonds, influencing crystal packing.
Area of Science:
- Crystallography
- Organic Chemistry
- Supramolecular Chemistry
Background:
- Understanding molecular arrangements in crystals is crucial for predicting material properties.
- Diaryl ketone derivatives are common motifs in organic synthesis and materials science.
- Hydrogen bonding plays a significant role in directing crystal packing and intermolecular interactions.
Purpose of the Study:
- To determine and analyze the crystal structure of the title compound, C(26)H(26)O(2).
- To investigate the conformational preferences of the 1,5-dione chain and the orientation of the tolyl rings.
- To identify and characterize intermolecular interactions, specifically hydrogen bonding, within the crystal lattice.
Main Methods:
- Single-crystal X-ray diffraction was employed to obtain the crystal structure data.
- Analysis of bond lengths, bond angles, and dihedral angles was performed.
- Identification of potential hydrogen bonding interactions (C-H⋯O) was conducted.
Main Results:
- The crystal structure of C(26)H(26)O(2) was successfully elucidated.
- Significant dihedral angles were observed between the terminal tolyl rings (70.3°) and between the central tolyl group and terminal rings (67.8°, 85.1°).
- Intermolecular C-H⋯O hydrogen bonds were identified between benzene/methylene carbon atoms and carbonyl oxygen atoms, leading to the formation of one-dimensional chains.
Conclusions:
- The conformational analysis reveals a non-planar arrangement of the tolyl rings within the 1,5-dione framework.
- The identified C-H⋯O hydrogen bonds are key stabilizing interactions that dictate the crystal packing and supramolecular architecture.
- The study provides insights into the solid-state behavior of this class of organic compounds.
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