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Updated: May 19, 2026
12:07
Microwave-assisted Intramolecular Dehydrogenative Diels-Alder Reactions for the Synthesis of Functionalized Naphthalenes/Solvatochromic Dyes
Published on: April 1, 2013
2,7-Dimeth-oxy-1-(2-naphtho-yl)naph-thalene.
Takehiro Tsumuki1, Atsumi Isogai, Atsushi Nagasawa
1Department of Organic and Polymer Materials Chemistry, Tokyo University of Agriculture & Technology, 2-24-16 Naka-machi, Koganei, Tokyo 184-8588, Japan.
Acta Crystallographica. Section E, Structure Reports Online
|August 21, 2012
Summary
This study details the molecular structure of a C(23)H(18)O(3) compound, revealing a significant dihedral angle between its naphthalene rings. Weak hydrogen bonding was observed in its crystal structure.
Area of Science:
- Crystallography
- Organic Chemistry
- Molecular Structure Analysis
Background:
- Understanding the three-dimensional arrangement of atoms in organic molecules is crucial for predicting their properties and reactivity.
- Naphthalene derivatives are important in materials science and medicinal chemistry.
Purpose of the Study:
- To elucidate the precise molecular geometry of a novel C(23)H(18)O(3) compound.
- To investigate the spatial relationship between the naphthalene ring systems and the bridging carbonyl group.
- To identify intermolecular interactions within the crystal lattice.
Main Methods:
- Single-crystal X-ray diffraction was employed to determine the molecular structure.
- Analysis of dihedral and torsion angles was performed to describe the conformation.
- Identification of hydrogen bonding interactions in the solid state.
Main Results:
- The dihedral angle between the two naphthalene ring systems was determined to be 80.44(4)°.
- The carbonyl group exhibited distinct torsion angles with each naphthalene unit (-68.55(17)° and -9.01(19)°).
- A weak C-H⋯O hydrogen bond was identified between the carbonyl oxygen and a naphthalene hydrogen atom of a symmetry-related molecule.
Conclusions:
- The study provides a detailed structural characterization of the C(23)H(18)O(3) molecule.
- The observed conformation highlights the non-planar arrangement of the fused ring systems.
- The identified weak hydrogen bond contributes to the crystal packing and stability.
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