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Related Concept Videos

Electrophilic Aromatic Substitution: Nitration of Benzene01:20

Electrophilic Aromatic Substitution: Nitration of Benzene

9.0K
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.
9.0K
Nucleophilic Aromatic Substitution: Elimination–Addition01:11

Nucleophilic Aromatic Substitution: Elimination–Addition

5.1K
Simple aryl halides do not react with nucleophiles. However, nucleophilic aromatic substitutions can be forced under certain conditions, such as high temperatures or strong bases. The mechanism of substitution under such conditions involves the highly unstable and reactive benzyne intermediate. Benzyne contains equivalent carbon centers at both ends of the triple bond, each of which is equally susceptible to nucleophilic attack. This 50–50 distribution of products is...
5.1K
meta-Directing Deactivators: –NO2, –CN, –CHO, –⁠CO2R, –COR, –CO2H01:13

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

6.9K
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...
6.9K
Nucleophilic Aromatic Substitution: Addition–Elimination (SNAr)01:30

Nucleophilic Aromatic Substitution: Addition–Elimination (SNAr)

4.9K
Nucleophilic substitution in aromatic compounds is feasible in substrates bearing strong electron-withdrawing substituents positioned ortho or para to the leaving group. The reaction proceeds via two steps: the addition of the nucleophile and the elimination of the leaving group.
The reaction begins with an attack of the nucleophile on the carbon that holds the leaving group. This results in the delocalization of the π electrons over the ring carbons. The resonance interaction between...
4.9K
Nucleophilic Aromatic Substitution of Aryldiazonium Salts: Aromatic SN101:14

Nucleophilic Aromatic Substitution of Aryldiazonium Salts: Aromatic SN1

2.8K
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,...
2.8K
Rate-Determining Steps03:08

Rate-Determining Steps

37.6K
Relating Reaction Mechanisms
In a multistep reaction mechanism, one of the elementary steps progresses significantly slower than the others. This slowest step is called the rate-limiting step (or rate-determining step). A reaction cannot proceed faster than its slowest step, and hence, the rate-determining step limits the overall reaction rate.
The concept of rate-determining step can be understood from the analogy of a 4-lane freeway with a short-stretch of traffic-bottleneck caused due to...
37.6K

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Related Experiment Video

Updated: Feb 22, 2026

Continuous Flow Chemistry: Reaction of Diphenyldiazomethane with p-Nitrobenzoic Acid
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Continuous Flow Chemistry: Reaction of Diphenyldiazomethane with p-Nitrobenzoic Acid

Published on: November 15, 2017

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A countercurrent microflow strategy for simultaneous high selectivity and conversion in aromatic nitration.

Jing Song1, Yongqi Pan1, Ruobing Xin1

  • 1State Key Laboratory of Chemical Engineering and Low-Carbon Technology, Department of Chemical Engineering, Tsinghua University, Beijing, China.

Nature Communications
|February 20, 2026
PubMed
Summary
This summary is machine-generated.

This study introduces a novel countercurrent microflow method for aromatic nitration, significantly enhancing reaction speed and selectivity. This approach overcomes long-standing challenges in controlling over-nitration, improving safety and efficiency in chemical synthesis.

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Area of Science:

  • Chemical Engineering
  • Organic Chemistry
  • Process Chemistry

Background:

  • Aromatic nitration is a critical industrial process with inherent safety risks.
  • A persistent challenge is the trade-off between reaction rate and selectivity, leading to problematic over-nitration.
  • Traditional batch reactors and co-current microflow systems exhibit limitations in efficiency and control.

Purpose of the Study:

  • To develop a microflow strategy that simultaneously enhances spatiotemporal conversion rate and selectivity in aromatic nitration.
  • To address and mitigate the issue of over-nitration, a common side reaction.
  • To demonstrate the versatility of the proposed method across different aromatic nitration reactions.

Main Methods:

  • Implementation of a countercurrent microflow mode utilizing two microreactors.
  • Investigation of the reaction kinetics and thermodynamics within the microreactor system.
  • Identification of the role of water in inhibiting over-nitration through in situ reduction of nitroaromatic dissolution.

Main Results:

  • The countercurrent microflow mode achieved a five-fold increase in spatiotemporal conversion rate compared to co-current flow.
  • A two-orders-of-magnitude improvement in conversion rate was observed relative to traditional batch reactors.
  • An effective inhibition mechanism for over-nitration was identified, linked to water generation during the reaction.
  • Simultaneous achievement of high conversion and selectivity, overcoming the traditional trade-off effect.

Conclusions:

  • The proposed countercurrent microflow strategy offers a significant advancement in aromatic nitration processes.
  • This method provides enhanced safety, efficiency, and control, overcoming key limitations of existing technologies.
  • The demonstrated broad applicability suggests potential for widespread adoption in various nitration applications.