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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-[(Dimethyl-amino)(phen-yl)meth-yl]naphthalen-2-ol
1Ordered Matter Science Research Center, College of Chemistry and Chemical Engineering, Southeast University, Nanjing 210096, People's Republic of China.
This study details the molecular structure of C(19)H(19)NO, revealing a significant dihedral angle between its naphthyl and phenyl rings. An intramolecular hydrogen bond and van der Waals forces stabilize its unique conformation.
Area of Science:
- Organic Chemistry
- Crystallography
- Molecular Structure
Background:
- Understanding molecular conformation is crucial in chemistry.
- Specific interactions dictate the three-dimensional arrangement of atoms in molecules.
Purpose of the Study:
- To elucidate the precise molecular conformation of the title compound, C(19)H(19)NO.
- To identify the key interactions responsible for stabilizing this conformation.
Main Methods:
- Single-crystal X-ray diffraction was employed to determine the molecular structure.
- Analysis of bond lengths, angles, and intermolecular contacts was performed.
Main Results:
- The dihedral angle between the naphthyl and phenyl ring systems was precisely measured at 79.83(6)°.
- An intramolecular O-H⋯N hydrogen bond was identified as a key stabilizing feature.
- Van der Waals interactions were also found to contribute to the molecular conformation.
Conclusions:
- The molecular conformation of C(19)H(19)NO is significantly influenced by the dihedral angle between its aromatic systems.
- Intramolecular hydrogen bonding and van der Waals forces play critical roles in stabilizing this specific arrangement.
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