Related Experiment Video
Updated: Jul 10, 2026
![Solid-phase Synthesis of [4.4] Spirocyclic Oximes](/_next/image?url=https%3A%2F%2Fcloudfront.jove.com%2FCDNSource%2Fteasers%2F58508.jpg&w=3840&q=50)
Solid-phase Synthesis of [4.4] Spirocyclic Oximes
Published on: February 6, 2019
(5Z)-4-Amino-2-(4-hydroxyphenyl)-1H-imidazol-5(2H)-one oxime 3-oxide
Xue Qin Cao1, Zhan Xiong Li, Guo Qiang Chen
1School of Materials Engineering, Suzhou University, Suzhou 215021, People's Republic of China.
This study introduces a novel molecule with perpendicular benzene and imidazole rings, featuring a unique hydroxyimino group. This discovery opens avenues for new chemical reactions and potential applications.
Area of Science:
- Organic Chemistry
- Crystallography
- Supramolecular Chemistry
Background:
- The synthesis and characterization of novel organic compounds are crucial for advancing chemical science.
- Understanding the structural and electronic properties of molecules informs their potential applications.
- The formation of extended networks through intermolecular interactions is a key area in supramolecular chemistry.
Purpose of the Study:
- To synthesize and characterize a novel organic molecule with a unique structural motif.
- To investigate the crystal structure and intermolecular interactions of the title compound.
- To explore the potential reactivity and applications stemming from the molecule's unique features.
Main Methods:
- Single-crystal X-ray diffraction was employed to determine the molecular and crystal structure.
- Spectroscopic techniques were used for characterization.
- Analysis of intermolecular interactions, including pi-pi stacking and hydrogen bonding, was performed.
Main Results:
- A novel molecule, C(9)H(10)N(4)O(3), was synthesized and structurally characterized.
- The crystal structure reveals nearly perpendicular benzene and imidazole rings.
- A unique hydroxyimino group attached to the imidazole ring via a C=N double bond was observed, representing a first in this compound class.
- Extensive three-dimensional hydrogen-bonding networks and pi-pi interactions between overlapping aromatic rings were identified.
Conclusions:
- The title molecule possesses a unique structural architecture with potential for diverse chemical transformations.
- The observed intermolecular interactions suggest possibilities for designing extended supramolecular structures.
- This work provides a foundation for exploring the reactivity and applications of this new class of compounds.
More Related Videos
07:30A Direct, Regioselective and Atom-Economical Synthesis of 3-Aroyl-N-hydroxy-5-nitroindoles by Cycloaddition of 4-Nitronitrosobenzene with Alkynones
Published on: January 21, 2020
06:18Syntheses, Crystallization, and Spectroscopic Characterization of 3,5-Lutidine N-Oxide Dehydrate
Published on: April 24, 2018
Related Concept Videos
Structure and Nomenclature of Epoxides
Preparation of Amines: Reduction of Oximes and Nitro Compounds
Though catalytic hydrogenation can reduce nitrobenzenes, the reduction is nonselective in the presence of other functional groups. For instance, if nitrobenzene contains an aldehyde group,...
Aldehydes and Ketones with Amines: Imine and Enamine Formation Overview
Five-Membered Heterocyclic Aromatic Compounds: Overview
Aldehydes and Ketones with Amines: Imine Formation Mechanism
Imines are formed under mildly acidic conditions. A pH of 4.5 is ideal for the reaction.
If the pH is low or the solution is too acidic, the reaction slows down in the...
Preparation of 1° Amines: Hofmann and Curtius Rearrangement Overview