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Updated: Apr 28, 2026

Microwave-assisted Intramolecular Dehydrogenative Diels-Alder Reactions for the Synthesis of Functionalized Naphthalenes/Solvatochromic Dyes
Published on: April 1, 2013
Zwitterionic 1-{(E)-[(2-methyl-phen-yl)iminium-yl]meth-yl}naphthalen-2-olate
Ammar Khelifa Baghdouche1, Salima Mosbah1, Youghourta Belhocine1
1Laboratoire de Chimie des Matériaux, Faculté des Sciences Exactes, Département de Chimie, Université Constantine 1, Algeria.
This study details the crystal structure of a zwitterionic Schiff base (C18H15NO). Key findings include an N-H⋯O hydrogen bond forming an S(6) ring and weak aromatic π-π stacking interactions.
Area of Science:
- Crystal engineering and supramolecular chemistry.
- Organic solid-state chemistry.
Background:
- Schiff bases are versatile organic compounds with diverse applications.
- Understanding their solid-state structures is crucial for material design.
Purpose of the Study:
- To elucidate the crystal structure of the title Schiff base (C18H15NO).
- To investigate intermolecular interactions, including hydrogen bonding and π-π stacking.
Main Methods:
- Single-crystal X-ray diffraction analysis.
- Analysis of hydrogen bonding and non-covalent interactions.
Main Results:
- The Schiff base crystallizes in a zwitterionic form.
- An intramolecular N-H⋯O hydrogen bond forms a six-membered S(6) ring.
- A dihedral angle of 36.91° exists between the aromatic ring systems.
- Weak aromatic π-π stacking was observed with a minimum centroid-centroid separation of 3.7771 Å.
Conclusions:
- The zwitterionic nature and specific hydrogen bonding dictate the crystal packing.
- Aromatic π-π stacking contributes to the overall crystal lattice stability.
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