1-[(Phenyl-iminio)amino]-2-naphtho-late
1Hubei Key Laboratory of Pollutant Analysis & Reuse Technology, College of Chemistry and Environmental Engineering, Hubei Normal University, Huangshi, Hubei 435002, People's Republic of China.
This study characterizes a novel zwitterionic compound, C(16)H(12)N(2)O, detailing its molecular structure and crystal packing. Key findings include a specific dihedral angle and strong π-π interactions facilitating molecular assembly.
Area of Science:
- Crystallography
- Organic Chemistry
- Supramolecular Chemistry
Background:
- Understanding the structural and electronic properties of organic molecules is crucial for designing new materials.
- Zwitterionic compounds, possessing both positive and negative charges, exhibit unique chemical behaviors.
- Azo compounds are versatile building blocks in organic synthesis and materials science.
Purpose of the Study:
- To elucidate the crystal structure and intermolecular interactions of the title zwitterionic compound.
- To investigate the conformational preferences and hydrogen bonding in the solid state.
- To analyze the role of π-π stacking in the crystal packing.
Main Methods:
- Single-crystal X-ray diffraction was employed to determine the molecular and crystal structure.
- Analysis of bond lengths, bond angles, and dihedral angles provided conformational insights.
- Intermolecular interactions, including hydrogen bonding and π-π stacking, were systematically studied.
Main Results:
- The title compound, C(16)H(12)N(2)O, crystallizes as a zwitterion.
- A small dihedral angle of 2.0(1)° between the benzene and naphthalene ring systems was observed.
- The azo group is in a trans configuration, and an intramolecular N-H⋯O hydrogen bond was identified.
- Strong π-π interactions with a centroid-centroid distance of 3.375(3) Å govern the crystal packing.
Conclusions:
- The study provides a detailed structural characterization of a novel zwitterionic azo compound.
- The observed intramolecular hydrogen bond and significant π-π stacking interactions play key roles in stabilizing the crystal structure.
- These findings contribute to the understanding of structure-property relationships in zwitterionic organic materials.
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