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Updated: Jun 5, 2026

A Two-Step Protocol for Umpolung Functionalization of Ketones Via Enolonium Species
Published on: August 16, 2018
(E)-2-[(2-Chloro-phen-yl)imino-meth-yl]-4-methyl-phenol
This study reveals the enol-imine tautomeric form of a C14H12ClNO molecule, stabilized by intramolecular hydrogen bonds and intermolecular C-H⋯π interactions in its crystal structure.
Area of Science:
- Crystallography
- Organic Chemistry
- Molecular Structure
Background:
- Understanding tautomerism is crucial in organic chemistry.
- Intramolecular hydrogen bonding influences molecular conformation.
- Intermolecular interactions dictate crystal packing.
Purpose of the Study:
- To elucidate the tautomeric form of the title compound (C14H12ClNO).
- To investigate the role of hydrogen bonding in molecular structure.
- To analyze the intermolecular forces governing crystal formation.
Main Methods:
- Single-crystal X-ray diffraction was employed.
- Structural analysis focused on bond lengths, angles, and non-covalent interactions.
- Conformational analysis of the molecule was performed.
Main Results:
- The molecule exists in the enol-imine tautomeric form.
- A significant intramolecular O-H⋯N hydrogen bond was identified.
- The two benzene rings exhibit a twist of 30.6(2)°.
- Crystal structure is stabilized by intermolecular C-H⋯π interactions.
Conclusions:
- The enol-imine tautomer is the predominant form in the solid state.
- Intramolecular hydrogen bonding plays a key role in stabilizing this conformation.
- Intermolecular C-H⋯π interactions are essential for the observed crystal packing.
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