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Updated: Jun 1, 2026

A Two-Step Protocol for Umpolung Functionalization of Ketones Via Enolonium Species
Published on: August 16, 2018
2-Eth-oxy-6-[(methyl-imino)-meth-yl]phenol.
Cheng Min Ge1, Shu-Hua Zhang, Feng Chao
1College of Chemistry and Bioengineering, Guilin University of Technology, Guilin 541004, People's Republic of China.
This study details the synthesis of a novel compound, C(10)H(13)NO(2). The research highlights an intramolecular hydrogen bond within the molecule and intermolecular hydrogen bonds forming dimers in its crystal structure.
Area of Science:
- Organic Chemistry
- Crystallography
- Supramolecular Chemistry
Background:
- Benzaldehyde derivatives are important in organic synthesis.
- Hydrogen bonding plays a crucial role in molecular structure and crystal packing.
- Understanding intermolecular interactions is key to materials science.
Purpose of the Study:
- To synthesize and characterize a new organic compound, C(10)H(13)NO(2).
- To investigate the presence and nature of intramolecular hydrogen bonding.
- To analyze the crystal structure and intermolecular interactions.
Main Methods:
- Chemical synthesis involving 2-hydroxy-3-ethoxy-benzaldehyde and methylamine.
- Single-crystal X-ray diffraction for structural analysis.
- Analysis of hydrogen bonding networks (O-H⋯N and C-H⋯O).
Main Results:
- Successful synthesis of the target compound C(10)H(13)NO(2).
- Identification of a significant intramolecular O-H⋯N hydrogen bond.
- Observation of molecular self-assembly into inversion dimers via C-H⋯O hydrogen bonds in the crystal lattice.
Conclusions:
- The synthesized compound exhibits distinct intramolecular hydrogen bonding.
- Crystal packing is governed by intermolecular C-H⋯O hydrogen bonds, leading to dimer formation.
- Structural insights contribute to the understanding of hydrogen bonding in organic molecules.
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