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

Preparation of 1° Amines: Azide Synthesis01:22

Preparation of 1° Amines: Azide Synthesis

Direct alkylation of ammonia produces polyalkylated amines, along with a quaternary ammonium salt. To exclusively prepare primary amines, the azide synthesis method can be used.
Azide ions act as good nucleophiles and react with unhindered alkyl halides to form alkyl azides. Alkyl azides do not participate in further nucleophilic substitution reactions, thereby eliminating the chances of polyalkylated products. Alkyl azides are reduced by hydride-based reducing agents, like lithium aluminum...
Aryldiazonium Salts to Azo Dyes: Diazo Coupling01:11

Aryldiazonium Salts to Azo Dyes: Diazo Coupling

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 position.
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...
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.
Diazonium Group Substitution with Halogens and Cyanide: Sandmeyer and Schiemann Reactions01:20

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

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

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

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.

You might also read

Related Articles

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

Sort by
Same author

Improper geometric ferroelectricity at the monolayer limit.

Science advances·2026
Same author

Evolution and Suppression of Spin Cycloid in Epitaxial BiFeO<sub>3</sub> Thin Films.

Advanced materials (Deerfield Beach, Fla.)·2026
Same author

Biosynthesis of the Selenium-Substituted [FeFe]-Hydrogenases.

Journal of the American Chemical Society·2026
Same author

Revealing buried ferroelectric topologies by depth-resolved electron diffraction imaging.

Nature communications·2026
Same author

Author Correction: Magnon confinement in epitaxial antiferromagnetic oxide heterostructures.

Nature materials·2026
Same author

Magnon confinement in epitaxial antiferromagnetic oxide heterostructures.

Nature materials·2026

Related Experiment Video

Updated: May 17, 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

A New Route to Azadithiolato Complexes.

Raja Angamuthu1, Maria E Carroll, Maya Ramesh

  • 1Department of Chemistry, University of Illinois at Urbana-Champaign, Urbana, IL 61801, USA.

European Journal of Inorganic Chemistry
|November 6, 2012
PubMed
Summary
This summary is machine-generated.

New titanium-based azadithiolate complexes were synthesized and characterized. These findings demonstrate the stability of azadithiolate ligands on mononuclear metal centers and their potential for further chemical transformations.

More Related Videos

Synthesis of a Thiol Building Block for the Crystallization of a Semiconducting Gyroidal Metal-sulfur Framework
12:30

Synthesis of a Thiol Building Block for the Crystallization of a Semiconducting Gyroidal Metal-sulfur Framework

Published on: April 9, 2018

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

Preparation of N-(2-alkoxyvinyl)sulfonamides from N-tosyl-1,2,3-triazoles and Subsequent Conversion to Substituted Phthalans and Phenethylamines

Published on: January 3, 2018

Related Experiment Videos

Last Updated: May 17, 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

Synthesis of a Thiol Building Block for the Crystallization of a Semiconducting Gyroidal Metal-sulfur Framework
12:30

Synthesis of a Thiol Building Block for the Crystallization of a Semiconducting Gyroidal Metal-sulfur Framework

Published on: April 9, 2018

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

Preparation of N-(2-alkoxyvinyl)sulfonamides from N-tosyl-1,2,3-triazoles and Subsequent Conversion to Substituted Phthalans and Phenethylamines

Published on: January 3, 2018

Area of Science:

  • Organometallic Chemistry
  • Coordination Chemistry
  • Titanium Chemistry

Background:

  • Titanium complexes with sulfur-containing ligands are of interest due to their diverse reactivity.
  • Cyclic imines offer a route to novel ligand architectures.

Purpose of the Study:

  • To synthesize and characterize novel 2-aza-1,3-dithiolato chelate complexes of titanium.
  • To investigate the structural and dynamic properties of these new complexes.
  • To explore the reactivity of these complexes with iron carbonyl compounds.

Main Methods:

  • Synthesis of titanium azadithiolate complexes via reaction of titanium bis(dithiolato) precursors with cyclic imines.
  • Characterization using 1H NMR spectroscopy, ESI-mass spectrometry, and X-ray crystallography.
  • Variable-temperature 1H NMR studies to probe ligand dynamics.
  • Reaction of a titanium azadithiolate complex with an iron carbonyl precursor.

Main Results:

  • Successfully synthesized three novel 2-aza-1,3-dithiolato chelate complexes: [(MeC5H4)2Ti{(SCH2)2NR}] (1, R = Ph; 2, R = Me; 3, R = CH2Ph).
  • Demonstrated the existence of azadithiolate ligands on mononuclear titanium centers.
  • X-ray crystallography confirmed the chelate structure.
  • Variable-temperature 1H NMR revealed ring inversion dynamics of the dithiolate ligands.
  • A new iron complex, [Fe2{(SCH2)2NPh}(CO)6], was obtained from the reaction of complex 1 with [Fe(benzylideneacetone)(CO)3].

Conclusions:

  • Azadithiolate ligands can be stabilized on mononuclear titanium centers.
  • The synthesized titanium complexes exhibit dynamic behavior in solution.
  • These complexes serve as precursors for the synthesis of novel iron-sulfur clusters.