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Updated: Jun 5, 2026

Microwave-assisted Intramolecular Dehydrogenative Diels-Alder Reactions for the Synthesis of Functionalized Naphthalenes/Solvatochromic Dyes
Published on: April 1, 2013
1-(4-Chloro-benzo-yl)-2,7-dimethoxy-naphthalene
This study details the crystal structure of a chlorinated organic compound, C(19)H(15)ClO(3). Researchers identified a significant dihedral angle and an intermolecular hydrogen bond influencing its molecular arrangement.
Area of Science:
- Organic Chemistry
- Crystallography
- Molecular Structure
Background:
- Understanding the three-dimensional arrangement of atoms in organic molecules is crucial for predicting their properties and reactivity.
- Crystal structure analysis provides precise details about molecular geometry, conformation, and intermolecular interactions.
Purpose of the Study:
- To elucidate the crystal structure of the title compound, C(19)H(15)ClO(3).
- To analyze the dihedral angle between the naphthalene and benzene rings.
- To investigate intermolecular interactions, specifically hydrogen bonding, within the crystal lattice.
Main Methods:
- Single-crystal X-ray diffraction was employed to determine the molecular and crystal structure.
- Analysis of bond lengths, bond angles, and dihedral angles provided geometric insights.
- Identification and analysis of intermolecular interactions, including hydrogen bonds, were performed.
Main Results:
- The dihedral angle between the naphthalene and benzene ring systems was determined to be 72.06(7)°.
- The 4-chlorophenyl group and the carbonyl group were found to be nearly coplanar.
- An intermolecular C-H⋯O hydrogen bond was identified, connecting the 4-chlorophenyl group to a methoxy group and forming a zigzag chain along the a axis.
Conclusions:
- The crystal structure of C(19)H(15)ClO(3) reveals specific conformational preferences and the influence of substituents.
- The observed intermolecular hydrogen bonding plays a role in the packing and stability of the crystal structure.
- Detailed structural information contributes to the broader understanding of halogenated aromatic compounds.
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