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Related Concept Videos

Diazonium Group Substitution: –OH and –H01:19

Diazonium Group Substitution: –OH and –H

2.8K
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.
2.8K
Diazonium Group Substitution with Halogens and Cyanide: Sandmeyer and Schiemann Reactions01:20

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

1.9K
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...
1.9K
Nucleophilic Aromatic Substitution of Aryldiazonium Salts: Aromatic SN101:14

Nucleophilic Aromatic Substitution of Aryldiazonium Salts: Aromatic SN1

2.1K
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,...
2.1K
Aryldiazonium Salts to Azo Dyes: Diazo Coupling01:11

Aryldiazonium Salts to Azo Dyes: Diazo Coupling

2.9K
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...
2.9K
Preparation of 1° Amines: Azide Synthesis01:22

Preparation of 1° Amines: Azide Synthesis

3.9K
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...
3.9K
1° Amines to Diazonium or Aryldiazonium Salts: Diazotization with NaNO2 Mechanism01:37

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

3.8K
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.
3.8K

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Updated: Jun 26, 2025

Preparation of Stable Bicyclic Aziridinium Ions and Their Ring-Opening for the Synthesis of Azaheterocycles
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Comparative Analysis of the Hydrazine Interaction with Arylene Diimide Derivatives: Complementary Approach Using

Aditya Tiwari1, Rikitha S Fernandes2, Nilanjan Dey2

  • 1Department of Electrical and Electronics Engineering, Birla Institute of Technology and Science-Pilani, Hyderabad Campus, Hyderabad 500078, India.

Langmuir : the ACS Journal of Surfaces and Colloids
|May 15, 2024
PubMed
Summary
This summary is machine-generated.

Perlyene diimide (PDI) and naphthyl diimide (NDI) sensors show promise for detecting analytes. PDI-GLU, functionalized with glutamic acid, emerged as the optimal hydrazine sensor due to strong hydrogen bonding interactions.

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Isolating Free Carbenes, their Mixed Dimers and Organic Radicals
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Area of Science:

  • Materials Science
  • Chemical Sensing
  • Computational Chemistry

Background:

  • Perylene diimide (PDI) and naphthyl diimide (NDI) based sensors exhibit high sensitivity to various gaseous analytes.
  • A systematic understanding of molecular interactions for optical transduction in NDI/PDI sensors is lacking, hindering performance optimization.

Purpose of the Study:

  • To investigate and rationalize the molecular-level interactions governing hydrazine adsorption on engineered NDI/PDI scaffolds.
  • To compare the efficacy of different amino acid functionalized NDI/PDI derivatives as hydrazine sensors.

Main Methods:

  • Ab initio calculations were employed to study hydrazine adsorption on four NDI/PDI derivatives functionalized with alanine (ALA) and glutamic acid (GLU).
  • Analysis focused on adsorption energy, charge transfer, and recovery time, alongside molecular energy spectrum variations.
  • Experimental validation utilized UV-visible spectroscopy, NMR, EPR, and FT-IR studies.

Main Results:

  • Carboxylic acid (COOH) groups on the scaffolds serve as primary interaction sites for hydrazine via hydrogen bonding.
  • Glutamic acid (GLU) functional groups, with more COOH groups and stronger secondary interactions, enhance hydrazine binding compared to alanine (ALA).
  • Perylene diimide (PDI) derivatives showed more favorable HOMO/LUMO gap changes upon hydrazine interaction.

Conclusions:

  • PDI-GLU was identified as the most effective hydrazine host molecule among the studied derivatives due to combined electronic and binding properties.
  • Theoretical predictions were experimentally validated, confirming the interaction mechanism and the superiority of PDI-GLU for hydrazine sensing.