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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
2-[(2-Bromo-phen-yl)imino-meth-yl]-6-methyl-phenol
Summary
This study details the solid-state structure of a novel Schiff base compound. Its phenol-imine tautomerism and intramolecular hydrogen bonding were characterized, revealing specific molecular geometry.
Area of Science:
- Organic Chemistry
- Crystallography
- Supramolecular Chemistry
Background:
- Schiff bases are versatile organic compounds with diverse applications.
- Understanding the solid-state behavior of Schiff bases is crucial for their material applications.
- Tautomerism influences the chemical and physical properties of molecules.
Purpose of the Study:
- To characterize the crystal structure of a specific Schiff base, C(14)H(12)BrNO.
- To investigate the tautomeric form adopted by the compound in the solid state.
- To analyze the molecular geometry, including dihedral angles and hydrogen bonding.
Main Methods:
- Single-crystal X-ray diffraction was employed to determine the molecular structure.
- Analysis of bond lengths, bond angles, and dihedral angles.
- Identification and analysis of intra-molecular interactions, such as hydrogen bonds.
Main Results:
- The compound crystallizes as a Schiff base adopting the phenol-imine tautomeric form.
- A significant dihedral angle of 34.26(9)° was observed between the two aromatic rings.
- An intra-molecular O-H⋯N hydrogen bond was identified, forming a stable S(6) ring.
Conclusions:
- The solid-state structure confirms the phenol-imine tautomerism in this Schiff base.
- The observed molecular geometry and hydrogen bonding provide insights into crystal packing and intermolecular interactions.
- This structural information is valuable for the design of related functional organic materials.
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