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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
3-[(3-Hydroxypropyl)amino]-1-phenyl-but-2-en-1-one
T S Arul Jeevan1, K S Nagaraja
1Department of Chemistry, Loyola Institute of Frontier Energy, Loyola College, Chennai 600 034, India.
Summary
This study reveals the molecular structure of C(13)H(17)NO(2), detailing its intramolecular hydrogen bond and planar ring formation. Molecules self-assemble into helical chains via intermolecular hydrogen bonds, showcasing crystal structure dynamics.
Area of Science:
- Crystallography
- Chemical Physics
Background:
- Understanding molecular interactions is crucial for predicting material properties.
- Hydrogen bonding plays a significant role in molecular self-assembly and crystal engineering.
Purpose of the Study:
- To elucidate the crystal structure of the title compound, C(13)H(17)NO(2).
- To investigate the role of intra- and intermolecular hydrogen bonding in the compound's structural organization.
Main Methods:
- Single-crystal X-ray diffraction was employed to determine the molecular and crystal structure.
- Analysis of hydrogen bonding networks and geometric parameters was performed.
Main Results:
- The title compound exhibits an intramolecular N-H⋯O hydrogen bond, forming a near-planar six-membered ring.
- An intermolecular O-H⋯O hydrogen bond links molecules into helical chains along the b-axis through 2(1) screw symmetry and b-translation.
- The dihedral angle between the planar ring and the phenyl group is 7.19(8)°.
Conclusions:
- The compound's crystal structure is dictated by a combination of intramolecular and intermolecular hydrogen bonding.
- The observed helical chains highlight the directional nature of hydrogen bonding in crystal packing.
- The structural data provides fundamental insights into the solid-state behavior of this molecule.
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