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Related Concept Videos

Electrophilic Aromatic Substitution: Nitration of Benzene01:20

Electrophilic Aromatic Substitution: Nitration of Benzene

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.
Preparation of Amines: Reduction of Oximes and Nitro Compounds01:29

Preparation of Amines: Reduction of Oximes and Nitro Compounds

Oximes can be reduced to primary amines using catalytic hydrogenation, hydride reduction, or sodium metal reduction. The reduction of aliphatic and aromatic nitro compounds to primary amines takes place by either catalytic hydrogenation or by using active metals like Fe, Zn, and Sn in the presence of an acid.
Though catalytic hydrogenation can reduce nitrobenzenes, the reduction is nonselective in the presence of other functional groups. For instance, if nitrobenzene contains an aldehyde group,...
2° Amines to N-Nitrosamines: Reaction with NaNO201:20

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.
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...
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...
meta-Directing Deactivators: –NO2, –CN, –CHO, –⁠CO2R, –COR, –CO2H01:13

meta-Directing Deactivators: –NO2, –CN, –CHO, –⁠CO2R, –COR, –CO2H

All meta-directing substituents are deactivating groups. These substituents withdraw electrons from the aromatic ring, making the ring less reactive toward electrophilic substitution. For example, the nitration of nitrobenzene is 100,000 times slower than that of benzene because of the deactivating effect of the nitro group. The first step in an electrophilic aromatic substitution is the addition of an electrophile to form a resonance-stabilized carbocation. The energy diagrams for the...

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Related Experiment Video

Updated: Jun 12, 2026

A Direct, Regioselective and Atom-Economical Synthesis of 3-Aroyl-N-hydroxy-5-nitroindoles by Cycloaddition of 4-Nitronitrosobenzene with Alkynones
07:30

A Direct, Regioselective and Atom-Economical Synthesis of 3-Aroyl-N-hydroxy-5-nitroindoles by Cycloaddition of 4-Nitronitrosobenzene with Alkynones

Published on: January 21, 2020

Nitroaromatic compounds, from synthesis to biodegradation.

Kou-San Ju1, Rebecca E Parales

  • 1Department of Microbiology, College of Biological Sciences, University of California, 226 Briggs Hall, 1 Shields Ave., Davis, CA 95616, USA.

Microbiology and Molecular Biology Reviews : MMBR
|May 29, 2010
PubMed
Summary
This summary is machine-generated.

Microorganisms can degrade nitroaromatic compounds, which are industrial chemicals that contaminate soil and groundwater. This review explores the bacteria and pathways involved in nitroaromatic compound biodegradation.

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A General Method for Detecting Nitrosamide Formation in the In Vitro Metabolism of Nitrosamines by Cytochrome P450s
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A General Method for Detecting Nitrosamide Formation in the In Vitro Metabolism of Nitrosamines by Cytochrome P450s

Published on: September 25, 2017

On-line Analysis of Nitrogen Containing Compounds in Complex Hydrocarbon Matrixes
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On-line Analysis of Nitrogen Containing Compounds in Complex Hydrocarbon Matrixes

Published on: August 5, 2016

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Last Updated: Jun 12, 2026

A Direct, Regioselective and Atom-Economical Synthesis of 3-Aroyl-N-hydroxy-5-nitroindoles by Cycloaddition of 4-Nitronitrosobenzene with Alkynones
07:30

A Direct, Regioselective and Atom-Economical Synthesis of 3-Aroyl-N-hydroxy-5-nitroindoles by Cycloaddition of 4-Nitronitrosobenzene with Alkynones

Published on: January 21, 2020

A General Method for Detecting Nitrosamide Formation in the In Vitro Metabolism of Nitrosamines by Cytochrome P450s
07:38

A General Method for Detecting Nitrosamide Formation in the In Vitro Metabolism of Nitrosamines by Cytochrome P450s

Published on: September 25, 2017

On-line Analysis of Nitrogen Containing Compounds in Complex Hydrocarbon Matrixes
07:49

On-line Analysis of Nitrogen Containing Compounds in Complex Hydrocarbon Matrixes

Published on: August 5, 2016

Area of Science:

  • Environmental microbiology
  • Biochemistry
  • Industrial chemistry

Background:

  • Nitroaromatic compounds (NACs) are synthetic industrial chemicals crucial for products like dyes, polymers, pesticides, and explosives.
  • Widespread use has resulted in significant soil and groundwater contamination.
  • The nitro group imparts recalcitrance to biodegradation due to its electron-withdrawing nature and the stable benzene ring, compounded by toxicity and mutagenicity.

Purpose of the Study:

  • To review the synthesis of both natural and synthetic nitroaromatic compounds.
  • To identify bacteria capable of degrading and mineralizing nitroaromatic compounds.
  • To elucidate the biodegradation pathways and discuss their evolutionary origins.

Main Methods:

  • Literature review of synthesis and biodegradation pathways of nitroaromatic compounds.
  • Identification and characterization of microbial strains that metabolize nitroaromatic compounds.
  • Analysis of enzymatic pathways involved in nitroaromatic compound degradation.

Main Results:

  • Overview of synthetic and biogenic nitroaromatic compound production.
  • Identification of diverse bacterial strains capable of complete nitroaromatic compound mineralization.
  • Detailed description of evolved biodegradation pathways utilized by these microorganisms.

Conclusions:

  • Microorganisms have evolved remarkable metabolic capabilities to utilize nitroaromatic compounds as nutrient sources.
  • Understanding these biodegradation pathways is crucial for developing effective environmental remediation strategies.
  • Further research into the evolutionary origins of these pathways can provide insights into microbial adaptation.