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2° Amines to N-Nitrosamines: Reaction with NaNO201:20

2° Amines to N-Nitrosamines: Reaction with NaNO2

5.9K
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.
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1° Amines to Diazonium or Aryldiazonium Salts: Diazotization with NaNO2 Mechanism01:37

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

5.4K
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.
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1° Amines to Diazonium or Aryldiazonium Salts: Diazotization with NaNO2 Overview01:26

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

4.1K
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...
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Electrophilic Aromatic Substitution: Nitration of Benzene01:20

Electrophilic Aromatic Substitution: Nitration of Benzene

10.0K
The nitration of benzene is an example of an electrophilic aromatic substitution reaction. It involves the formation of a very powerful electrophile, the nitronium ion, which is linear in shape. The reaction occurs through the interaction of two strong acids, sulfuric and nitric acid.
10.0K
Nucleophilic Aromatic Substitution of Aryldiazonium Salts: Aromatic SN101:14

Nucleophilic Aromatic Substitution of Aryldiazonium Salts: Aromatic SN1

3.1K
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,...
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Diazonium Group Substitution: –OH and –H01:19

Diazonium Group Substitution: –OH and –H

3.5K
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.
3.5K

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Self-assembled discrete molecules for sensing nitroaromatics.

Sankarasekaran Shanmugaraju1, Partha Sarathi Mukherjee

  • 1Department of Inorganic and Physical Chemistry, Indian Institute of Science, Bangalore 560 012 (India).

Chemistry (Weinheim an Der Bergstrasse, Germany)
|February 20, 2015
PubMed
Summary

Researchers developed novel electron-rich molecular sensors for detecting trace nitroaromatic explosives. These sensors, including metallacycles and cages, effectively detect explosives in solution and vapor phases via fluorescence quenching.

Keywords:
molecular recognitionnanostructuresnitroaromaticsplatinumself-assembly

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Area of Science:

  • Supramolecular Chemistry
  • Analytical Chemistry
  • Materials Science

Background:

  • Nitroaromatic compounds (NACs) are key components of explosives and environmental pollutants.
  • Efficient detection of trace NACs is crucial for national security and environmental monitoring.
  • Existing sensing methods face challenges in sensitivity and applicability.

Purpose of the Study:

  • To design and synthesize novel electron-rich molecular sensors for nitroaromatic explosives.
  • To evaluate the sensing performance of these architectures in both solution and vapor phases.
  • To explore the potential of supramolecular interactions in developing advanced explosive sensors.

Main Methods:

  • Rational design and synthesis of π-electron-rich fluorescent metallacycles (squares, rectangles, tweezers) and metallacages (prisms).
  • Utilizing metal-ligand coordination-bonding interactions for self-assembly.
  • Investigating supramolecular interactions for accommodating NACs within sensor cavities.
  • Monitoring fluorescence quenching as a detection mechanism for NACs.

Main Results:

  • Successfully synthesized various fluorescent metallacycles and metallacages with internal spaces.
  • Demonstrated effective sensing of nitroaromatics (e.g., picric acid, TNT, DNT) in solution and vapor phases.
  • Observed significant fluorescence quenching upon interaction with trace amounts of NACs.
  • Highlighted the role of multiple supramolecular interactions in the sensing process.

Conclusions:

  • Electron-rich molecular architectures, including metallacycles and cages, are highly effective for sensing nitroaromatic explosives.
  • The developed sensors exhibit excellent sensitivity, enabling detection of trace quantities.
  • These findings pave the way for future advancements in explosive detection technologies.