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Updated: Jun 1, 2026

Microwave-assisted Intramolecular Dehydrogenative Diels-Alder Reactions for the Synthesis of Functionalized Naphthalenes/Solvatochromic Dyes
Published on: April 1, 2013
2,7-Dimethoxy--1-(4-nitro-benzo-yl)-naphthalene
Shoji Watanabe1, Kosuke Nakaema, Takahiro Nishijima
1Department of Organic and Polymer Materials Chemistry, Tokyo University of Agriculture and Technology, Koganei, Tokyo 184-8588, Japan.
This study details the crystal structure of a novel organic compound, revealing specific dihedral angles and intermolecular interactions. These findings contribute to understanding molecular packing and bonding in crystalline organic materials.
Area of Science:
- Crystallography
- Organic Chemistry
- Materials Science
Background:
- Understanding the three-dimensional arrangement of atoms in organic molecules is crucial for predicting their properties.
- Intermolecular forces, such as hydrogen bonds and pi-pi interactions, significantly influence crystal packing and material characteristics.
Purpose of the Study:
- To elucidate the crystal structure of the title compound, C(19)H(15)NO(5).
- To analyze the dihedral angles between aromatic ring systems and the bridging carbonyl group.
- To identify and characterize intermolecular interactions 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 torsion angles provided insights into molecular geometry.
- Identification of non-covalent interactions, including C-H···π, π-π stacking, and C-H···O hydrogen bonds.
Main Results:
- The dihedral angle between the naphthalene and benzene rings is 61.97°.
- A significant dihedral angle of 54.68° was observed between the naphthalene system and the bridging carbonyl plane.
- The nitro group and phenyl ring exhibit near-coplanarity (torsion angle 2.94°).
- Molecules are linked by C-H···π interactions, and phenyl rings engage in π-π stacking.
- Weak C-H···O hydrogen bonds were identified between methoxy and carbonyl groups.
Conclusions:
- The crystal structure of C(19)H(15)NO(5) reveals a non-planar conformation with distinct dihedral angles.
- Intermolecular C-H···π, π-π stacking, and C-H···O interactions play a key role in stabilizing the crystal structure.
- These structural insights are valuable for the design of novel organic materials with tailored properties.
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