Jove
Visualize
Contact Us
JoVE
x logofacebook logolinkedin logoyoutube logo
ABOUT JoVE
OverviewLeadershipBlogJoVE Help Center
AUTHORS
Publishing ProcessEditorial BoardScope & PoliciesPeer ReviewFAQSubmit
LIBRARIANS
TestimonialsSubscriptionsAccessResourcesLibrary Advisory BoardFAQ
RESEARCH
JoVE JournalMethods CollectionsJoVE Encyclopedia of ExperimentsArchive
EDUCATION
JoVE CoreJoVE BusinessJoVE Science EducationJoVE Lab ManualFaculty Resource CenterFaculty Site
Terms & Conditions of Use
Privacy Policy
Policies

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.
NMR Spectroscopy of Benzene Derivatives01:37

NMR Spectroscopy of Benzene Derivatives

Simple unsubstituted benzene has six aromatic protons, all chemically equivalent. Therefore, benzene exhibits only a singlet peak at δ 7.3 ppm in the 1H NMR spectrum. The observed shift is far downfield because the aromatic ring current strongly deshields the protons. Any substitution on the benzene ring makes the aromatic protons nonequivalent, and the protons split each other. The peak is, therefore, no longer a singlet and the splitting pattern and their associated coupling constants depend...
Diazonium Group Substitution: –OH and –H01:19

Diazonium Group Substitution: –OH and –H

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

Nucleophilic Aromatic Substitution: Elimination–Addition

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 confirmed through isotopic...

You might also read

Related Articles

Articles linked to this work by shared authors, journal, and citation graph.

Sort by
Same author

Detection of ionisable lipids in equine plasma by supported liquid extraction and liquid chromatography-high-resolution tandem mass spectrometry for doping control of mRNA agents.

Journal of chromatography. A·2026
Same author

Chemical-Assembled Macrophage-Engaging Glypican-3 × Signal Regulatory Protein-α (SIRP-α) Bispecific Antibody for Immunotherapy Against Liver Cancer.

MedComm·2026
Same author

Biomimetic TME-Responsive Nanotheranostics for Precise NIR-II Ratiometric Photoacoustic Imaging and Synergistic Immuno-Photothermal Therapy.

Small (Weinheim an der Bergstrasse, Germany)·2026
Same author

Direct LC-HRMS/MS characterisation and RT-qPCR detection for potential mRNA-based doping agent.

Analytical and bioanalytical chemistry·2026
Same author

NIR-II Imaging-Guided Photothermal Activation of a TRPV4-Targeted Nanoplatform Delivering Cycloastragenol to Promote Microglia Reprogramming and α-Synuclein Clearance in Parkinson's Disease.

Advanced science (Weinheim, Baden-Wurttemberg, Germany)·2026
Same author

Mechanistic Insights Into Protein Aggregation Inhibition by Green-Synthesized Silver Nanoparticles: A Study on Human Lysozyme.

IET nanobiotechnology·2026

Related Experiment Video

Updated: May 25, 2026

Color Spot Test As a Presumptive Tool for the Rapid Detection of Synthetic Cathinones
06:06

Color Spot Test As a Presumptive Tool for the Rapid Detection of Synthetic Cathinones

Published on: February 5, 2018

N-(4-Bromo-phen-yl)-3,5-dinitro-benzamide.

Sohail Saeed, Naghmana Rashid, Rizwan Hussain

    Acta Crystallographica. Section E, Structure Reports Online
    |January 20, 2012
    PubMed
    Summary

    This study reveals the crystal structure of a brominated organic molecule, C(13)H(8)BrN(3)O(5). Molecular analysis shows twisted benzene rings and stabilization through hydrogen bonds and pi-pi interactions.

    Area of Science:

    • Organic Chemistry
    • Crystallography

    Background:

    • Understanding the solid-state structure of organic molecules is crucial for predicting their properties.
    • Brominated organic compounds can exhibit unique electronic and structural characteristics.

    Purpose of the Study:

    • To elucidate the crystal structure of the title molecule, C(13)H(8)BrN(3)O(5).
    • To investigate the intermolecular interactions stabilizing the crystal lattice.

    Main Methods:

    • Single-crystal X-ray diffraction was employed to determine the molecular and crystal structure.
    • Analysis of hydrogen bonding and π-π interactions was performed.

    Main Results:

    • The molecule C(13)H(8)BrN(3)O(5) exhibits a slightly twisted conformation with a dihedral angle of 5.9° between its benzene rings.

    More Related Videos

    Palladium N-Heterocyclic Carbene Complexes: Synthesis from Benzimidazolium Salts and Catalytic Activity in Carbon-carbon Bond-forming Reactions
    19:58

    Palladium N-Heterocyclic Carbene Complexes: Synthesis from Benzimidazolium Salts and Catalytic Activity in Carbon-carbon Bond-forming Reactions

    Published on: July 30, 2017

    Synthesis of Antiviral Tetrahydrocarbazole Derivatives by Photochemical and Acid-catalyzed C-H Functionalization via Intermediate Peroxides (CHIPS)
    06:34

    Synthesis of Antiviral Tetrahydrocarbazole Derivatives by Photochemical and Acid-catalyzed C-H Functionalization via Intermediate Peroxides (CHIPS)

    Published on: June 20, 2014

    Related Experiment Videos

    Last Updated: May 25, 2026

    Color Spot Test As a Presumptive Tool for the Rapid Detection of Synthetic Cathinones
    06:06

    Color Spot Test As a Presumptive Tool for the Rapid Detection of Synthetic Cathinones

    Published on: February 5, 2018

    Palladium N-Heterocyclic Carbene Complexes: Synthesis from Benzimidazolium Salts and Catalytic Activity in Carbon-carbon Bond-forming Reactions
    19:58

    Palladium N-Heterocyclic Carbene Complexes: Synthesis from Benzimidazolium Salts and Catalytic Activity in Carbon-carbon Bond-forming Reactions

    Published on: July 30, 2017

    Synthesis of Antiviral Tetrahydrocarbazole Derivatives by Photochemical and Acid-catalyzed C-H Functionalization via Intermediate Peroxides (CHIPS)
    06:34

    Synthesis of Antiviral Tetrahydrocarbazole Derivatives by Photochemical and Acid-catalyzed C-H Functionalization via Intermediate Peroxides (CHIPS)

    Published on: June 20, 2014

  • N-H⋯O hydrogen bonds form one-dimensional chains along the [101] direction.
  • π-π interactions, with a shortest centroid-centroid distance of 3.6467(17) Å, further stabilize the crystal structure.

    • Conclusions:

    • The crystal structure is characterized by specific hydrogen bonding and π-π stacking interactions.
    • These interactions dictate the overall packing and stability of the molecule in the solid state.