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

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.
Basicity of Heterocyclic Aromatic Amines01:25

Basicity of Heterocyclic Aromatic Amines

Heterocyclic amines, where the N atom is a part of an alicyclic system, are similar in basicity to alkylamines. Interestingly, the heterocyclic amine having a nitrogen atom as part of an aromatic ring has much less basicity than its corresponding alicyclic counterpart. For this reason, as presented in Figure 1, piperidine (pKb = 2.8) is significantly more basic than pyridine (pKb = 8.8).
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.
1° Amines to Diazonium or Aryldiazonium Salts: Diazotization with NaNO2 Overview01:26

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

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 water loss...
¹³C NMR: Distortionless Enhancement by Polarization Transfer (DEPT)01:20

¹³C NMR: Distortionless Enhancement by Polarization Transfer (DEPT)

When proton-coupled carbon-13 spectra are simplified by a broadband proton decoupling technique, structural information about the coupled protons is lost. Distortionless enhancement by polarization transfer (DEPT) is a technique that provides information on the number of hydrogens attached to each carbon in a molecule. While the DEPT experiment utilizes complex pulse sequences, the pulse delay and flip angle are specifically manipulated. The resulting signals have different phases depending on...
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...

You might also read

Related Articles

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

Sort by
Same author

Mercury Sulfide Nanoparticles Constitute a Long-Term Bioavailable Pool of Mercury in Soil-Rice Systems.

Journal of agricultural and food chemistry·2026
Same author

LIFT+: Lightweight Fine-Tuning for Long-Tail Learning.

IEEE transactions on pattern analysis and machine intelligence·2026
Same author

Lianxia Xiaopi Granules for Treatment of Functional Dyspepsia: A Multicenter, Randomized, Double-Blind and Placebo-Controlled Trial.

Chinese journal of integrative medicine·2026
Same author

Precise ^{136}Xe Double Beta Decay Measurement in PandaX-4T with Implications on the Nuclear Matrix Elements and Majorons.

Physical review letters·2026
Same author

Hulled Rice or husk? Synchrotron radiation XRF and deep learning approach for the determination of the geographical origin of Chinese rice samples.

Food chemistry·2026
Same author

Recent advances in spasmolytic polypeptide expressing metaplasia research.

World journal of gastrointestinal oncology·2026

Related Experiment Video

Updated: Jun 5, 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

N-Phenyl-piperidine-1-carbothio-amide.

Yu-Feng Li1, Fang-Fang Jian

  • 1Microscale Science Institute, Weifang University, Weifang 261061, People's Republic of China.

Acta Crystallographica. Section E, Structure Reports Online
|January 5, 2011
PubMed
Summary

A novel C(12)H(16)N(2)S compound was synthesized using phenyl isothiocyanate and piperidine. Its crystal structure reveals intermolecular N-H⋯S and intramolecular C-H⋯S/C-H⋯N hydrogen bonds, offering insights into molecular interactions.

More Related Videos

Modification and Functionalization of the Guanidine Group by Tailor-made Precursors
09:45

Modification and Functionalization of the Guanidine Group by Tailor-made Precursors

Published on: April 27, 2017

Development of a Backbone Cyclic Peptide Library as Potential Antiparasitic Therapeutics Using Microwave Irradiation
08:48

Development of a Backbone Cyclic Peptide Library as Potential Antiparasitic Therapeutics Using Microwave Irradiation

Published on: January 26, 2016

Related Experiment Videos

Last Updated: Jun 5, 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

Modification and Functionalization of the Guanidine Group by Tailor-made Precursors
09:45

Modification and Functionalization of the Guanidine Group by Tailor-made Precursors

Published on: April 27, 2017

Development of a Backbone Cyclic Peptide Library as Potential Antiparasitic Therapeutics Using Microwave Irradiation
08:48

Development of a Backbone Cyclic Peptide Library as Potential Antiparasitic Therapeutics Using Microwave Irradiation

Published on: January 26, 2016

Area of Science:

  • Organic Chemistry
  • Crystallography
  • Chemical Synthesis

Background:

  • Understanding molecular interactions is crucial in chemistry.
  • Hydrogen bonding plays a significant role in crystal structures.
  • Synthesis of novel compounds aids in expanding chemical knowledge.

Purpose of the Study:

  • To synthesize a new chemical compound with the formula C(12)H(16)N(2)S.
  • To elucidate the crystal structure of the synthesized compound.
  • To identify and analyze hydrogen bonding interactions within the crystal structure.

Main Methods:

  • Chemical synthesis involving phenyl isothiocyanate and piperidine.
  • Single-crystal X-ray diffraction for structural determination.
  • Analysis of intermolecular and intramolecular hydrogen bonds.

Main Results:

  • Successful synthesis of the title compound C(12)H(16)N(2)S.
  • Determination of the molecular and crystal structure.
  • Identification of intermolecular N-H⋯S hydrogen bonds.
  • Observation of weak intramolecular C-H⋯S and C-H⋯N hydrogen-bonding interactions.

Conclusions:

  • The synthesized compound C(12)H(16)N(2)S possesses a defined crystal structure.
  • Hydrogen bonding significantly influences the compound's solid-state arrangement.
  • The study contributes to the understanding of structure-property relationships in organic sulfur-nitrogen compounds.