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Updated: Jun 1, 2026
08:12
A Two-Step Protocol for Umpolung Functionalization of Ketones Via Enolonium Species
Published on: August 16, 2018
(1-Adamant-yl)(2-methyl-phen-yl)methanone
Summary
This study details the crystal structure of a C18H22O compound, revealing a significant dihedral angle between its carbonyl and benzene planes. The adamantyl group exhibits ideal chair conformations, with only van der Waals forces observed in the crystal lattice.
Area of Science:
- Crystallography
- Organic Chemistry
- Molecular Structure
Background:
- Understanding the three-dimensional arrangement of atoms in organic molecules is crucial for predicting their properties and reactivity.
- Adamantane derivatives are of interest due to their unique cage-like structure and applications in materials science and medicinal chemistry.
Purpose of the Study:
- To elucidate the precise molecular geometry and crystal packing of the title compound, C18H22O.
- To analyze the conformational preferences of the adamantyl group and the orientation of the carbonyl and benzene moieties.
Main Methods:
- Single-crystal X-ray diffraction was employed to determine the atomic coordinates and unit cell parameters.
- Geometric analyses were performed to calculate bond lengths, bond angles, and dihedral angles.
Main Results:
- The dihedral angle between the carbonyl and benzene planes was determined to be 69.11(6)°.
- The three fused cyclohexane rings within the adamantyl group adopt near-ideal chair conformations.
- Carbon-carbon-carbon bond angles within the adamantyl group range from 108.14(11)° to 110.50(11)°.
- No specific intermolecular interactions, beyond van der Waals forces, were identified in the crystal structure.
Conclusions:
- The crystal structure of C18H22O is characterized by a specific non-planar arrangement of its functional groups.
- The adamantyl cage maintains its characteristic strain-free chair conformations.
- The absence of strong intermolecular interactions suggests that crystal packing is dominated by weak van der Waals forces.
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