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Updated: Jun 5, 2026

Preparation of Stable Bicyclic Aziridinium Ions and Their Ring-Opening for the Synthesis of Azaheterocycles
Published on: August 22, 2018
Piperidinium 3-hydr-oxy-2-naphthoate.
Yong-Tao Wang1, Gui-Mei Tang, Yong-Chun Zhang
1Department of Chemical Engineering, Shandong Institute of Light Industry, Jinan, Shandong 250353, People's Republic of China.
Piperidine and 3-hydroxy-2-naphthoic acid form a salt with piperidinium cations in a chair conformation. These cations and anions link via hydrogen bonds, forming a stable crystal structure.
Area of Science:
- Crystallography
- Supramolecular Chemistry
- Organic Chemistry
Background:
- 3-hydroxy-2-naphthoic acid is an organic compound with potential applications in material science.
- Piperidine is a cyclic secondary amine commonly used in organic synthesis.
- Understanding the crystal structure of organic salts can provide insights into their physical and chemical properties.
Purpose of the Study:
- To synthesize and characterize the salt formed between 3-hydroxy-2-naphthoic acid and piperidine.
- To elucidate the crystal structure of the title salt.
- To investigate the intermolecular interactions within the crystal lattice.
Main Methods:
- Crystallization from a methanol/water solution.
- Single-crystal X-ray diffraction analysis.
Main Results:
- The title salt, C(5)H(12)N(+)·C(11)H(7)O(3) (-), was successfully obtained.
- Piperidinium cations adopt a chair conformation in the crystal structure.
- Hydrogen bonding interactions (N-H⋯O and C-H⋯O) were observed between cations and anions.
- An intramolecular O-H⋯O interaction was identified within the hydroxy-naphthoate anion.
Conclusions:
- The crystal structure reveals the specific arrangement and interactions of piperidinium cations and hydroxy-naphthoate anions.
- Hydrogen bonding plays a crucial role in stabilizing the crystal lattice.
- The findings contribute to the understanding of supramolecular assembly in organic salts.
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