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Related Concept Videos

Preparation of 1° Amines: Azide Synthesis01:22

Preparation of 1° Amines: Azide Synthesis

2.6K
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...
2.6K
1° Amines to Diazonium or Aryldiazonium Salts: Diazotization with NaNO2 Overview01:26

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

1.9K
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...
1.9K
Diazonium Group Substitution with Halogens and Cyanide: Sandmeyer and Schiemann Reactions01:20

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

2.0K
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...
2.0K
Diazonium Group Substitution: –OH and –H01:19

Diazonium Group Substitution: –OH and –H

1.9K
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.
1.9K
Aryldiazonium Salts to Azo Dyes: Diazo Coupling01:11

Aryldiazonium Salts to Azo Dyes: Diazo Coupling

3.2K
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...
3.2K
1° Amines to Diazonium or Aryldiazonium Salts: Diazotization with NaNO2 Mechanism01:37

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

3.3K
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.
3.3K

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Preparation and In Vivo Use of an Activity-based Probe for N-acylethanolamine Acid Amidase
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3,3-Dinitro-azetidinium chloride.

Biao Yan1, Hong-Ya Li, Ning-Ning Zhao

  • 1School of Chemistry and Chemical Engineering, Yulin University, Yulin 719000 Shaanxi, People's Republic of China ; School of Chemical Engineering, Northwest University, Xi'an 710069 Shaanxi, People's Republic of China.

Acta Crystallographica. Section E, Structure Reports Online
|March 12, 2013
PubMed
Summary
This summary is machine-generated.

This study characterizes the gem-dinitro-azetidinium chloride salt, revealing its planar azetidine ring and specific nitro group orientation. Crystal analysis shows ions linked by hydrogen bonds, forming chains and layers.

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

  • Crystallography
  • Inorganic Chemistry
  • Materials Science

Background:

  • Azetidinium salts are nitrogen-containing heterocycles with potential applications in various chemical fields.
  • Understanding the structural and bonding characteristics of novel energetic materials is crucial for their development and safe handling.

Purpose of the Study:

  • To elucidate the crystal structure and molecular geometry of the gem-dinitro-azetidinium chloride salt.
  • To investigate the intermolecular interactions governing the crystal packing of this energetic salt.

Main Methods:

  • Single-crystal X-ray diffraction was employed to determine the three-dimensional structure of the title compound.
  • Analysis of bond lengths, bond angles, and intermolecular interactions (hydrogen bonding) was performed.

Main Results:

  • The crystal structure of gem-dinitro-azetidinium chloride was determined, with cations and anions located on a mirror plane.
  • The azetidine ring was found to be nearly planar (mean deviation of 0.0569 Å).
  • A dihedral angle of 90.00(5)° was observed between the two nitro groups. N-H⋯Cl and C-H⋯O hydrogen bonds link the ions into chains and layers.

Conclusions:

  • The gem-dinitro-azetidinium chloride salt exhibits a well-defined crystal structure with a planar azetidine core.
  • Intermolecular hydrogen bonding plays a significant role in organizing the crystal lattice, forming extended chain and layered structures.