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Updated: Jun 1, 2026
06:46
Facile Preparation of (2Z,4E)-Dienamides by the Olefination of Electron-deficient Alkenes with Allyl Acetate
Published on: June 21, 2017
(E)-1-(2-Thien-yl)-3-(3,4,5-trimethoxy-phen-yl)prop-2-en-1-one
Summary
This study details the crystal structure of a novel heteroaryl chalcone. Researchers identified specific molecular conformations and intermolecular interactions, revealing face-to-side chains formed by weak hydrogen bonds.
Area of Science:
- Organic Chemistry
- Crystallography
- Materials Science
Background:
- Chalcones are versatile organic compounds with diverse biological and chemical properties.
- Heteroaryl chalcones, incorporating heterocyclic rings, offer unique structural and electronic characteristics.
- Understanding the solid-state structure of these molecules is crucial for predicting their reactivity and applications.
Purpose of the Study:
- To elucidate the crystal structure of a specific heteroaryl chalcone (C16H16O4S).
- To analyze the molecular conformation, including dihedral angles and methoxy group orientations.
- To investigate the intermolecular interactions governing the crystal packing.
Main Methods:
- Single-crystal X-ray diffraction analysis was employed to determine the molecular and crystal structure.
- Analysis of bond lengths, bond angles, and torsion angles provided insights into molecular geometry.
- Intermolecular interactions, such as C-H⋯O hydrogen bonds, were identified and characterized.
Main Results:
- The heteroaryl chalcone molecule exhibits a slightly twisted conformation with a dihedral angle of 12.18(4)° between the thiophene and trimethoxyphenyl rings.
- Two methoxy groups are nearly coplanar with the benzene ring, while the third adopts a (-)-synclinal conformation.
- Adjacent molecules form face-to-side chains along the c-axis via C-H⋯O(enone) interactions, which are further stacked by C-H⋯O(methoxy) interactions.
Conclusions:
- The study provides a detailed structural characterization of the title heteroaryl chalcone.
- The observed crystal packing is dictated by specific weak intermolecular interactions, influencing the overall solid-state architecture.
- This structural information serves as a foundation for further investigations into the properties and potential applications of this class of compounds.
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