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

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

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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...
5.7K
1° Amines to Diazonium or Aryldiazonium Salts: Diazotization with NaNO2 Mechanism01:37

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

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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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Electrophilic Aromatic Substitution: Nitration of Benzene01:20

Electrophilic Aromatic Substitution: Nitration of Benzene

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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.
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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

3.5K
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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Preparation of Amines: Reduction of Oximes and Nitro Compounds01:29

Preparation of Amines: Reduction of Oximes and Nitro Compounds

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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,...
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Nitrosation of Enols01:19

Nitrosation of Enols

3.7K
The nitrosation reaction is one of the methods of preparing 1,2-diketones. The enol tautomer of the starting ketone reacts with sodium nitrite in hydrochloric acid, generating the 1,2-diketone after hydrolysis.
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Related Experiment Video

Updated: Sep 2, 2025

Chemiluminescence-based Assays for Detection of Nitric Oxide and its Derivatives from Autoxidation and Nitrosated Compounds
08:23

Chemiluminescence-based Assays for Detection of Nitric Oxide and its Derivatives from Autoxidation and Nitrosated Compounds

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NTO Degradation by Nitroreductase: A DFT Study.

Liudmyla K Sviatenko1, Leonid Gorb2, Jerzy Leszczynski1

  • 1Interdisciplinary Center for Nanotoxicity, Department of Chemistry, Physics & Atmospheric Sciences, Jackson State University, Jackson, Mississippi 39217, United States.

The Journal of Physical Chemistry. B
|August 4, 2022
PubMed
Summary
This summary is machine-generated.

5-nitro-1,2,4-triazol-3-one (NTO) environmental degradation occurs via nitroreductase enzymes. Computational studies reveal NTO transforms into 5-amino-1,2,4-triazol-3-one (ATO) through sequential electron and proton transfers facilitated by the flavin mononucleotide (FMN) cofactor.

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Area of Science:

  • Environmental Chemistry
  • Biocatalysis
  • Computational Chemistry

Background:

  • 5-nitro-1,2,4-triazol-3-one (NTO) is an energetic material with potential environmental release during its lifecycle.
  • Understanding NTO's environmental degradation pathways is crucial for risk assessment and remediation strategies.

Purpose of the Study:

  • To elucidate the detailed mechanism of NTO reduction by oxygen-insensitive nitroreductase.
  • To investigate the role of the flavin mononucleotide (FMN) cofactor in NTO transformation.

Main Methods:

  • Computational study employing the PCM(Pauling)/M06-2X/6-311++G(d,p) level of theory.
  • Analysis of sequential electron and proton transfer steps involved in NTO reduction.

Main Results:

  • NTO is sequentially reduced to 5-amino-1,2,4-triazol-3-one (ATO) via nitroso and hydroxylamino intermediates.
  • The reduction mechanism involves electron and proton transfers from the FMN cofactor, with potential hydride transfer for nitroso reduction.
  • Low activation energies and high exothermicity indicate favorable reaction pathways.

Conclusions:

  • Oxygen-insensitive nitroreductase, utilizing FMN, efficiently catalyzes NTO degradation in the environment.
  • The computational findings support the significant role of FMN-containing enzymes in the environmental breakdown of NTO.