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Diazonium Group Substitution: –OH and –H

Diazonium 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.

1° Amines to Diazonium or Aryldiazonium Salts: Diazotization with NaNO2 Mechanism

1° 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.

1° Amines to Diazonium or Aryldiazonium Salts: Diazotization with NaNO2 Overview

1° 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...

2° Amines to N-Nitrosamines: Reaction with NaNO2

2° 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.

Carboxylic Acids to Methylesters: Alkylation using Diazomethane

Carboxylic 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.

Diazonium Group Substitution with Halogens and Cyanide: Sandmeyer and Schiemann Reactions

Diazonium 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...

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(E)-3-[1-(2,4-Difluoro-phen-yl)eth-yl]-5-methyl-N-nitro-1,3,5-oxadiazinan-4-imine.

Yuan-Yuan Zhong¹, Cong-Cong Li, Liang-Zhong Xu

¹College of Chemistry and Molecular Engineering, Qingdao University of Science and Technology, Qingdao 266042, People's Republic of China.

Acta Crystallographica. Section E, Structure Reports Online

|May 19, 2011

Summary

The crystal structure of a fluorinated oxadiazinane compound reveals an intermediate conformation. Weak intermolecular forces, including C-H⋯O hydrogen bonds and π-π interactions, stabilize the molecular arrangement in the solid state.

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Area of Science:

Crystallography
Organic Chemistry
Structural Chemistry

Background:

The 1,3,5-oxadiazinane ring is a heterocyclic scaffold with potential applications.
Understanding the conformational preferences and intermolecular interactions of such rings is crucial for predicting their chemical behavior and material properties.

Purpose of the Study:

To elucidate the crystal structure and conformational characteristics of a specific fluorinated 1,3,5-oxadiazinane derivative.
To investigate the intermolecular forces, such as hydrogen bonding and π-π interactions, that govern the crystal packing.

Main Methods:

Single-crystal X-ray diffraction analysis was employed to determine the three-dimensional structure.
Analysis of the crystal structure involved identifying and quantifying weak intermolecular interactions.

Main Results:

The 1,3,5-oxadiazinane ring adopts a conformation intermediate between a half-chair and a screw-boat form.
The crystal lattice is stabilized by weak intermolecular C-H⋯O hydrogen bonds.
Evidence for weak π-π interactions between neighboring benzene rings was observed, characterized by specific centroid-centroid and inter-planar distances.

Conclusions:

The study provides detailed structural insights into a fluorinated 1,3,5-oxadiazinane compound.
The findings highlight the significant role of weak intermolecular forces in the self-assembly and stabilization of organic crystals.
The conformational flexibility of the oxadiazinane ring and its packing in the solid state are important structural features.