Related Experiment Video
Updated: Jun 1, 2026
12:27
Synthesis of Hypervalent Iodonium Alkynyl Triflates for the Application of Generating Cyanocarbenes
Published on: September 8, 2013
1,2-Diazinium hydrogen chloranilate.
Kazuma Gotoh1, Hiroyuki Ishida
1Department of Chemistry, Faculty of Science, Okayama University, Okayama 700-8530, Japan.
Summary
This study details the crystal structure of a compound containing 1,2-diazinium cations and hydrogen chloranilate anions. The structure reveals a complex three-dimensional network formed by various hydrogen bonds between the cations and anions.
Area of Science:
- Crystallography
- Supramolecular Chemistry
- Materials Science
Background:
- Understanding the self-assembly of organic molecules is crucial for designing novel materials.
- Hydrogen bonding plays a pivotal role in dictating crystal packing and material properties.
Purpose of the Study:
- To elucidate the crystal structure of the title compound, C(4)H(5)N(2) (+)·C(6)HCl(2)O(4) (-).
- To investigate the hydrogen bonding interactions and supramolecular assembly within the crystal lattice.
Main Methods:
- Single-crystal X-ray diffraction analysis was employed to determine the three-dimensional structure.
- Analysis of hydrogen bonding (O-H⋯O, N-H⋯O, C-H⋯O, C-H⋯N) was performed.
Main Results:
- The crystal structure comprises three independent 1,2-diazinium cations and hydrogen chloranilate anions.
- Anions form dimers via O-H⋯O hydrogen bonds, with one dimer being centrosymmetric.
- Cations and anions associate into 2-2 arrangements through bifurcated N-H⋯O hydrogen bonds.
- Intermolecular C-H⋯O and C-H⋯N hydrogen bonds link these associations into molecular tapes.
- Further C-H⋯O hydrogen bonds connect the tapes into a 3D network.
Conclusions:
- The study reveals a complex supramolecular architecture driven by diverse hydrogen bonding interactions.
- The formation of a 3D network from 2-2 cation-anion associations highlights intricate molecular self-assembly.
- This detailed structural understanding provides insights into the solid-state behavior of such ionic compounds.
More Related Videos
Related Concept Videos
01:19Diazonium Group Substitution: –OH and –H
Nitrous acid, a weak acid, is prepared in situ via the reaction of sodium nitrite with a strong acid under cold conditions. This nitrous acid prepared in situ reacts with primary arylamines to form arenediazonium salts. Such reactions are known as diazotization reactions. As shown in Figure 1, the formation of arenediazonium salts begins with the decomposition of nitrous acid in an acidic solution to give nitrosonium ions.
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.
01:261° Amines to Diazonium or Aryldiazonium Salts: Diazotization with NaNO2 Overview
Nitrous acid and nitric acids are two types of acids containing nitrogen, among which nitrous acid is weaker than nitric acid. Nitrous acid with a pKa value of 3.37 ionizes in water to give a nitrite ion and the hydronium ion.
The nitrous acid is unstable. Hence, it is formed in situ from a solution of sodium nitrite and cold aqueous acids such as hydrochloric or sulfuric acid. In an acidic solution, the –OH group of nitrous acid undergoes protonation to give oxonium ion, followed by water loss...
The nitrous acid is unstable. Hence, it is formed in situ from a solution of sodium nitrite and cold aqueous acids such as hydrochloric or sulfuric acid. In an acidic solution, the –OH group of nitrous acid undergoes protonation to give oxonium ion, followed by water loss...
01:20Diazonium Group Substitution with Halogens and Cyanide: Sandmeyer and Schiemann Reactions
Arenediazonium substitution reactions occur when the diazonium group is substituted by various functional groups such as halides, hydroxyl, nitrile, etc. For instance, arenediazonium salts react with copper(I) salts of chloride, bromide, or cyanide to form corresponding aryl chlorides, bromides, and nitriles. These reactions are named Sandmeyer reactions. Although the mechanism of this reaction is complicated, as illustrated in Figure 1, they are believed to progress via an aryl copper...
01:14Nucleophilic Aromatic Substitution of Aryldiazonium Salts: Aromatic SN1
Treating arylamines with nitrous acid gives aryldiazonium salts that are effective substrates in nucleophilic aromatic substitution reactions. The diazonio group in these salts can be easily displaced by different nucleophiles, yielding a wide variety of substituted benzenes. The leaving group departs as nitrogen gas, and this easy elimination is the driving force for the substitution reaction.
In the Sandmeyer reaction, for example, the diazonio group is replaced by a chloro, bromo, or cyano...
In the Sandmeyer reaction, for example, the diazonio group is replaced by a chloro, bromo, or cyano...
01:11Aryldiazonium Salts to Azo Dyes: Diazo Coupling
The reaction of weakly electrophilic aryldiazonium (also called arenediazonium) salts with highly activated aromatic compounds leads to the formation of products with an —N=N— link, called an azo linkage. This reaction, presented in Figure 1, is known as diazo coupling and occurs without the loss of the nitrogen atoms of the aryldiazonium salt. Highly activated aromatic compounds such as phenols or arylamines favor the diazo coupling reaction. The coupling generally occurs at the para position.