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

Diazonium Group Substitution: –OH and –H01:19

Diazonium Group Substitution: –OH and –H

3.4K
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.
3.4K
Electrophilic Aromatic Substitution: Chlorination and Bromination of Benzene01:15

Electrophilic Aromatic Substitution: Chlorination and Bromination of Benzene

11.9K
Chlorination and bromination are important classes of electrophilic aromatic substitutions, where benzene reacts with chlorine or bromine in the presence of a Lewis acid catalyst to give halogenated substitution products. A Lewis acid such as aluminium chloride or ferric chloride catalyzes the chlorination, and ferric bromide catalyzes the bromination reactions. During the bromination of alkenes, bromine polarizes and becomes electrophilic. However, in the bromination of benzene, the bromine...
11.9K
Diazonium Group Substitution with Halogens and Cyanide: Sandmeyer and Schiemann Reactions01:20

Diazonium Group Substitution with Halogens and Cyanide: Sandmeyer and Schiemann Reactions

2.5K
Arenediazonium substitution reactions occur when the diazonium group is substituted by various functional groups such as halides, hydroxyl, nitrile, etc. For instance, arenediazonium salts react with copper(I) salts of chloride, bromide, or cyanide to form corresponding aryl chlorides, bromides, and nitriles. These reactions are named Sandmeyer reactions. Although the mechanism of this reaction is complicated, as illustrated in Figure 1, they are believed to progress via an aryl copper...
2.5K
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
Electrophilic Aromatic Substitution: Fluorination and Iodination of Benzene01:13

Electrophilic Aromatic Substitution: Fluorination and Iodination of Benzene

7.6K
Bromination and chlorination of aromatic rings by electrophilic aromatic substitution reactions are easily achieved, but fluorination and iodination are difficult to achieve. Fluorine is so reactive that its reaction with benzene is difficult to control, resulting in poor yields of monofluoroaromatic products. To address this, Selectfluor reagent is used as a fluorine source in which a fluorine atom is bonded to a positively charged nitrogen.
7.6K
Aryldiazonium Salts to Azo Dyes: Diazo Coupling01:11

Aryldiazonium Salts to Azo Dyes: Diazo Coupling

3.7K
The reaction of weakly electrophilic aryldiazonium (also called arenediazonium) salts with highly activated aromatic compounds leads to the formation of products with an —N=N— link, called an azo linkage. This reaction, presented in Figure 1, is known as diazo coupling and occurs without the loss of the nitrogen atoms of the aryldiazonium salt. Highly activated aromatic compounds such as phenols or arylamines favor the diazo coupling reaction. The coupling generally occurs at the para...
3.7K

You might also read

Related Articles

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

Sort by
Same author

GSH-activatable rare-earth nanoprobe for NIR-II fluorescence imaging-guided surgery and enhanced chemotherapy/chemodynamic therapy of breast cancer.

Cancer letters·2026
Same author

Systems-level regulation principles for microbial lignin valorization.

Current opinion in biotechnology·2026
Same author

A NIR-Ⅱ fluorescent probe for real-time visualization and early assessment of responses to CDK4/6 inhibitors in breast cancer.

Cancer letters·2026
Same author

TROP2-targeted NIR-II fluorescence imaging for visualizing surgical margins and metastatic sentinel lymph nodes in breast cancers.

Proceedings of the National Academy of Sciences of the United States of America·2026
Same author

Output Synchronization via Intermittent Dynamic Event-Triggered Sampled-Data Security Control for Delayed Reaction--Diffusion Neural Networks.

IEEE transactions on cybernetics·2026
Same author

Isoduprezianane-Type Sesquiterpene and Rare Isocedrenes from <i>Ainsliaea pertyoides</i> Franch. .

Journal of natural products·2025
Same journal

Crystal structure of 1-(piperidin-1-yl)butane-1,3-dione.

Acta crystallographica. Section E, Structure reports online·2015
Same journal

Crystal structure of methyl 1-methyl-3,5-diphenyl-7-tosyl-3,6,7,11b-tetra-hydro-pyrazolo-[4',3':5,6]pyrano[3,4-c]quinoline-5a(5H)-carboxyl-ate.

Acta crystallographica. Section E, Structure reports online·2015
Same journal

Crystal structure of 4-amino-1-(4-methyl-benz-yl)pyridinium bromide.

Acta crystallographica. Section E, Structure reports online·2015
Same journal

Crystal structure of (Z)-3-benz-yloxy-6-[(2-hy-droxy-anilino)methyl-idene]cyclo-hexa-2,4-dien-1-one.

Acta crystallographica. Section E, Structure reports online·2015
Same journal

Crystal structure of bis-(1-benzyl-1H-1,2,4-triazole) perchloric acid monosolvate.

Acta crystallographica. Section E, Structure reports online·2015
Same journal

Crystal structure of 2-(di-phenyl-phos-phanyl)phenyl 4-(hy-droxy-meth-yl)benzoate.

Acta crystallographica. Section E, Structure reports online·2015
See all related articles

Related Experiment Video

Updated: Feb 22, 2026

Preparation of Stable Bicyclic Aziridinium Ions and Their Ring-Opening for the Synthesis of Azaheterocycles
11:45

Preparation of Stable Bicyclic Aziridinium Ions and Their Ring-Opening for the Synthesis of Azaheterocycles

Published on: August 22, 2018

8.8K

Phenazin-5-ium bromide.

Gong-Xiao Zhang1, Ping Li, Jian Dong

  • 1Faculty of Chemistry and Chemical Engineering, TaiShan Medical University, Tai'an 271016, People's Republic of China.

Acta Crystallographica. Section E, Structure Reports Online
|July 17, 2012
PubMed
Summary
This summary is machine-generated.

This study details the crystal structure of a protonated tricyclic compound. Hydrogen bonds and π-π interactions dictate its molecular assembly in the solid state.

More Related Videos

Preparation of N-2-alkoxyvinylsulfonamides from N-tosyl-1,2,3-triazoles and Subsequent Conversion to Substituted Phthalans and Phenethylamines
10:42

Preparation of N-2-alkoxyvinylsulfonamides from N-tosyl-1,2,3-triazoles and Subsequent Conversion to Substituted Phthalans and Phenethylamines

Published on: January 3, 2018

10.3K
Preparation and Reactivity of a Triphosphenium Bromide Salt: A Convenient and Stable Source of PhosphorusI
08:46

Preparation and Reactivity of a Triphosphenium Bromide Salt: A Convenient and Stable Source of PhosphorusI

Published on: November 22, 2016

8.3K

Related Experiment Videos

Last Updated: Feb 22, 2026

Preparation of Stable Bicyclic Aziridinium Ions and Their Ring-Opening for the Synthesis of Azaheterocycles
11:45

Preparation of Stable Bicyclic Aziridinium Ions and Their Ring-Opening for the Synthesis of Azaheterocycles

Published on: August 22, 2018

8.8K
Preparation of N-2-alkoxyvinylsulfonamides from N-tosyl-1,2,3-triazoles and Subsequent Conversion to Substituted Phthalans and Phenethylamines
10:42

Preparation of N-2-alkoxyvinylsulfonamides from N-tosyl-1,2,3-triazoles and Subsequent Conversion to Substituted Phthalans and Phenethylamines

Published on: January 3, 2018

10.3K
Preparation and Reactivity of a Triphosphenium Bromide Salt: A Convenient and Stable Source of PhosphorusI
08:46

Preparation and Reactivity of a Triphosphenium Bromide Salt: A Convenient and Stable Source of PhosphorusI

Published on: November 22, 2016

8.3K

Area of Science:

  • Crystallography
  • Organic Chemistry
  • Supramolecular Chemistry

Background:

  • Understanding the solid-state packing of organic molecules is crucial for predicting material properties.
  • Tricyclic organic compounds exhibit diverse structural motifs and potential applications.

Purpose of the Study:

  • To elucidate the crystal structure and intermolecular interactions of a protonated tricyclic compound.
  • To analyze the role of hydrogen bonding and π-π stacking in the self-assembly of organic cations and anions.

Main Methods:

  • Single-crystal X-ray diffraction was employed to determine the molecular and crystal structure.
  • Analysis of hydrogen bonding (N-H⋯Br, C-H⋯Br) and π-π interactions was performed.

Main Results:

  • The protonated tricyclic system displays a slight twist between the outer benzene rings (dihedral angle of 3.9°).
  • Centrosymmetric assemblies are formed through N-H⋯Br and C-H⋯Br hydrogen bonds linking cations and anions.
  • These assemblies are further organized into stacks along the [010] direction via π-π interactions between aromatic rings (centroid-centroid distance = 3.725 Å).

Conclusions:

  • The crystal structure reveals specific hydrogen bonding patterns and π-π stacking interactions that govern the compound's solid-state organization.
  • The observed supramolecular architecture highlights the interplay between ionic and covalent interactions in driving molecular assembly.