Related Experiment Video
Updated: Jun 1, 2026
11:01
Preparation and In Vivo Use of an Activity-based Probe for N-acylethanolamine Acid Amidase
Published on: November 23, 2016
2-Carb-oxy-1-(3-nitro-phen-yl)ethanaminium perchlorate
1Ordered Matter Science Research Center, College of Chemistry and Chemical Engineering, Southeast University, Nanjing 210096, People's Republic of China.
Summary
This study reveals the crystal structure of a novel organic compound. Organic cations form dimers through hydrogen bonds, creating a 2D network with perchlorate anions.
Area of Science:
- Crystallography
- Supramolecular Chemistry
- Organic Chemistry
Background:
- Understanding the self-assembly of organic molecules is crucial for designing new materials.
- Hydrogen bonding plays a key role in dictating crystal packing and material properties.
Purpose of the Study:
- To elucidate the crystal structure and intermolecular interactions of the title compound, C(9)H(11)N(2)O(4) (+)·ClO(4) (-).
- To investigate the role of hydrogen bonding in the formation of supramolecular architectures.
Main Methods:
- Single-crystal X-ray diffraction analysis was employed to determine the molecular and crystal structure.
- Analysis of hydrogen bonding networks (O-H⋯O and N-H⋯O) was performed.
Main Results:
- The crystal structure revealed the formation of centrosymmetric dimers of organic cations through O-H⋯O hydrogen bonds between carboxyl groups.
- N-H⋯O interactions between the protonated amine group, perchlorate anions, and the nitro group resulted in a two-dimensional network parallel to the (001) plane.
Conclusions:
- The study successfully characterized the supramolecular assembly of the title compound.
- The observed hydrogen bonding patterns highlight the importance of specific interactions in directing crystal engineering and network formation.
Related Concept Videos
01:202° Amines to N-Nitrosamines: Reaction with NaNO2
Secondary amines react with nitrous acid to form N-nitrosamines, as depicted in Figure 1. Nitrous acid, a weak and unstable acid, is formed in situ from an aqueous solution of sodium nitrite and strong acids, such as hydrochloric acid or sulfuric acid, in cold conditions. In the presence of an acid, the nitrous acid gets protonated. The subsequent loss of water results in the formation of the electrophile known as nitrosonium ion.
01:28Structures of Carboxylic Acid Derivatives
Structure of Carboxylic Acid Derivatives
Carboxylic acid derivatives contain an acyl group attached to a heteroatom such as chlorine, oxygen, or nitrogen. The carbonyl carbon and oxygen are both sp2-hybridized with an unhybridized p orbital.
The three sp2 orbitals of the carbonyl carbon form three σ bonds, one each with the carbonyl oxygen, the α carbon, and the heteroatom, whereas the other two sp2 orbitals of the carbonyl oxygen are occupied by the lone pairs. Further, the unhybridized p...
Carboxylic acid derivatives contain an acyl group attached to a heteroatom such as chlorine, oxygen, or nitrogen. The carbonyl carbon and oxygen are both sp2-hybridized with an unhybridized p orbital.
The three sp2 orbitals of the carbonyl carbon form three σ bonds, one each with the carbonyl oxygen, the α carbon, and the heteroatom, whereas the other two sp2 orbitals of the carbonyl oxygen are occupied by the lone pairs. Further, the unhybridized p...
01:371° Amines to Diazonium or Aryldiazonium Salts: Diazotization with NaNO2 Mechanism
Nitrous acid is a relatively weak and unstable acid prepared in situ by the reaction of sodium nitrite and cold, dilute hydrochloric acid. In an acidic solution, the nitrous acid undergoes protonation when it loses water to form a nitrosonium ion—an electrophile. Nitrous acid reacts with primary amines to give diazonium salts. The reaction is called diazotization of primary amines.
01:15Enolate Mechanism Conventions
When a carbonyl compound is treated with a strong base, the α position gets deprotonated to give a resonance-stabilized intermediate called an enolate. Enolates are ambident nucleophiles because they possess two nucleophilic sites that can attack an electrophile owing to the delocalization of the negative charge between the α carbon and oxygen atoms. When the oxygen atom attacks an electrophile, it is called O-attack, whereas electrophilic attack via the α carbon is known as C-attack.
C-attack...
C-attack...
01:18Carboxylic Acids to Acid Chlorides
Carboxylic acids react with SOCl2 or PCl5 to form acid chlorides. Amongst the carboxylic acid derivatives, acid chlorides are the most reactive and synthetically important derivatives. They are useful reagents for Friedel–Crafts acylation of some aromatic compounds.
01:33Carboxylic Acids to Methylesters: Alkylation using Diazomethane
Carboxylic acids react with diazomethane in an ether solvent via alkylation at the carboxylate oxygen atom to give methyl esters of the corresponding acid with excellent yields.