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Updated: Jun 1, 2026
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Microwave-assisted Intramolecular Dehydrogenative Diels-Alder Reactions for the Synthesis of Functionalized Naphthalenes/Solvatochromic Dyes
Published on: April 1, 2013
(Naphthalene-1,4-di-yl)dimethyl dibenzoate
1Department of Chemistry, ZunYi Normal College, ZunYi 563002, People's Republic of China.
Summary
This study details the crystal structure of a C(26)H(20)O(4) compound, revealing a planar naphthalene system and specific dihedral angles between its aromatic rings and carboxylate group.
Area of Science:
- Crystallography
- Organic Chemistry
- Molecular Structure Analysis
Background:
- Understanding the precise 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 detailed crystal structure of the title compound, C(26)H(20)O(4).
- To analyze the planarity of the naphthalene ring system and the spatial orientation of the carboxylate and benzene groups.
Main Methods:
- Single-crystal X-ray diffraction was employed to determine the molecular and crystal structure.
- Crystallographic symmetry operations, specifically a 2-fold axis, were used to generate the complete molecule.
- Geometric analyses, including planarity assessments and dihedral angle calculations, were performed.
Main Results:
- The complete molecule of C(26)H(20)O(4) is generated by a crystallographic 2-fold axis.
- The naphthalene ring system exhibits planarity within 0.05(4) Å.
- Significant dihedral angles were observed between the carboxylate (-COO) plane, the benzene ring, and the naphthalene system (12.83(3)° and 12.93(1)°).
- The carboxylate plane and the benzene ring are nearly coplanar, with a small dihedral angle of 2.59(8)°.
Conclusions:
- The crystal structure of C(26)H(20)O(4) has been precisely determined.
- The molecule displays a planar naphthalene core with specific orientations of the attached functional groups.
- These structural details provide insights into the molecule's conformation and potential intermolecular interactions.
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