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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-[(4-Bromo-phen-yl)imino-meth-yl]-3,5-dimethoxy-phenol
Summary
This study reveals two similar molecules in the crystal structure of C(15)H(14)BrNO(3), both existing in a phenol-imine tautomeric form stabilized by intramolecular hydrogen bonds.
Area of Science:
- Crystallography
- Organic Chemistry
- Molecular Structure
Background:
- Understanding molecular configurations is crucial in organic chemistry.
- Tautomerism influences chemical properties and reactivity.
- Hydrogen bonding plays a significant role in stabilizing molecular structures.
Purpose of the Study:
- To elucidate the crystal structure of the title compound, C(15)H(14)BrNO(3).
- To investigate the tautomeric form and intermolecular interactions present.
- To analyze the geometric parameters and non-planarity of the molecules.
Main Methods:
- Single-crystal X-ray diffraction was employed to determine the molecular structure.
- Analysis of bond lengths, bond angles, and dihedral angles.
- Identification of hydrogen bonding networks and tautomeric forms.
Main Results:
- Two independent molecules of C(15)H(14)BrNO(3) were identified in the asymmetric unit, exhibiting similar geometries.
- Each molecule adopts the phenol-imine tautomeric form.
- Strong intramolecular O-H⋯N hydrogen bonds were observed, stabilizing the structure.
- The molecules are non-planar, with dihedral angles between aromatic rings measured at 24.6(2)° and 30.30(13)°.
Conclusions:
- The crystal structure of C(15)H(14)BrNO(3) features two similar phenol-imine tautomers.
- Intramolecular hydrogen bonding is a key stabilizing feature.
- The observed non-planarity provides insight into the molecule's three-dimensional conformation.
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