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Related Concept Videos

1° Amines to Diazonium or Aryldiazonium Salts: Diazotization with NaNO2 Mechanism01:37

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.
Diazonium Group Substitution: –OH and –H01:19

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.
Aryldiazonium Salts to Azo Dyes: Diazo Coupling01:11

Aryldiazonium 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.
1° Amines to Diazonium or Aryldiazonium Salts: Diazotization with NaNO2 Overview01:26

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...
Preparation of 1° Amines: Azide Synthesis01:22

Preparation of 1° Amines: Azide Synthesis

Direct alkylation of ammonia produces polyalkylated amines, along with a quaternary ammonium salt. To exclusively prepare primary amines, the azide synthesis method can be used.
Azide ions act as good nucleophiles and react with unhindered alkyl halides to form alkyl azides. Alkyl azides do not participate in further nucleophilic substitution reactions, thereby eliminating the chances of polyalkylated products. Alkyl azides are reduced by hydride-based reducing agents, like lithium aluminum...
Nucleophilic Aromatic Substitution of Aryldiazonium Salts: Aromatic SN101:14

Nucleophilic 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...

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Preparation of Stable Bicyclic Aziridinium Ions and Their Ring-Opening for the Synthesis of Azaheterocycles
11:45

Preparation of Stable Bicyclic Aziridinium Ions and Their Ring-Opening for the Synthesis of Azaheterocycles

Published on: August 22, 2018

1-(2,4-Dinitro-phen-yl)-3,3-dinitro-azetidine.

Biao Yan, Hai-Xia Ma, Yin Hu

    Acta Crystallographica. Section E, Structure Reports Online
    |May 18, 2011
    PubMed
    Summary

    This study details the molecular structure of a novel compound, C(9)H(7)N(5)O(8). Researchers determined the precise spatial arrangement and orientation of its azetidine and benzene rings, along with nitro groups.

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    Preparation of Contiguous Bisaziridines for Regioselective Ring-Opening Reactions
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    Preparation of Contiguous Bisaziridines for Regioselective Ring-Opening Reactions
    04:38

    Preparation of Contiguous Bisaziridines for Regioselective Ring-Opening Reactions

    Published on: July 28, 2022

    Area of Science:

    • Crystallography and Molecular Structure
    • Organic Chemistry
    • Nitrogen-Containing Heterocycles

    Background:

    • Understanding the three-dimensional structure of organic molecules is crucial for predicting their properties and reactivity.
    • Azetidine and benzene rings are common structural motifs in pharmaceuticals and materials science.
    • Nitro groups can significantly influence a molecule's electronic properties and reactivity.

    Purpose of the Study:

    • To elucidate the detailed crystal structure of the compound C(9)H(7)N(5)O(8).
    • To quantify the dihedral angle between the azetidine and benzene ring systems.
    • To describe the spatial orientation of the nitro groups attached to the azetidine ring.

    Main Methods:

    • Single-crystal X-ray diffraction analysis was employed to determine the molecular structure.
    • Geometric parameters, including bond lengths, bond angles, and dihedral angles, were precisely measured.
    • The crystal structure was refined to a high degree of accuracy.

    Main Results:

    • The title compound, C(9)H(7)N(5)O(8), was structurally characterized.
    • A dihedral angle of 26.1(1)° was measured between the mean planes of the azetidine and benzene rings.
    • The planes of the two nitro groups on the azetidine ring were found to be aligned at 88.7(1)°, indicating a near-perpendicular orientation.

    Conclusions:

    • The study provides precise structural data for C(9)H(7)N(5)O(8), contributing to the understanding of strained ring systems.
    • The observed dihedral angles offer insights into the conformational preferences and potential intermolecular interactions.
    • This detailed structural information can guide future synthetic efforts and applications of related compounds.