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

2° Amines to N-Nitrosamines: Reaction with NaNO201:20

2° Amines to N-Nitrosamines: Reaction with NaNO2

Secondary amines react with nitrous acid to form N-nitrosamines, as depicted in Figure 1. Nitrous acid, a weak and unstable acid, is formed in situ from an aqueous solution of sodium nitrite and strong acids, such as hydrochloric acid or sulfuric acid, in cold conditions. In the presence of an acid, the nitrous acid gets protonated. The subsequent loss of water results in the formation of the electrophile known as nitrosonium ion.
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.
Nomenclature of Aryl and Heterocyclic Amines01:10

Nomenclature of Aryl and Heterocyclic Amines

The simplest aromatic amine is phenylamine, which contains an –NH2 functionality directly attached to an aromatic ring. The name aniline is designated for this skeleton. As shown in Figure 1, the common names of the functionalized anilines involve prefixes ortho-, meta-, and para- to indicate the substitution position. Different functionalized aniline derivatives also have notable trivial names.
ortho–para-Directing Activators: –CH3, –OH, –⁠NH2, –OCH301:11

ortho–para-Directing Activators: –CH3, –OH, –⁠NH2, –OCH3

All ortho–para directors, excluding halogens, are activating groups. These groups donate electrons to the ring, making the ring carbons electron-rich. Consequently, the reactivity of the aromatic ring towards electrophilic substitution increases. For instance, the nitration of anisole is about 10,000 times faster than the nitration of benzene. The electron-donating effect of the methoxy group in anisole activates the ortho and para positions on the ring and stabilizes the corresponding...
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...

You might also read

Related Articles

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

Sort by
Same author

Crystal structure and Hirshfeld surface analyses, inter-action energy calculations and energy frameworks of (<i>Z</i>)-4-benzyl-2-(4-methyl-benzylidene)-2<i>H</i>-[1,4]benzo-thia-zin-3(4<i>H</i>)-one.

Acta crystallographica. Section E, Crystallographic communications·2026
Same author

An analogue of indapamide: crystal structure and Hirshfeld surface analysis of 3-chloro-4-(<i>N</i>,<i>N</i>-diethynylsulfamo-yl)-<i>N</i>-(2-meth-yl-indolin-1-yl)benzamide.

Acta crystallographica. Section E, Crystallographic communications·2026
Same author

Crystal structures, Hirshfeld surface analysis and inter-action energies of (<i>Z</i>)-2-(4-methyl-benzylidene)- and (<i>Z</i>)-2-(furfuryl-idene)-2<i>H</i>-benzo[<i>b</i>][1,4]thia-zin-3(4<i>H</i>)-one.

Acta crystallographica. Section E, Crystallographic communications·2025
Same author

Synthesis, crystal structure and Hirshfeld surface analysis of 1,1'-[oxybis(ethane-2,1-di-yl)]bis-(2-methyl-sulfanyl-1<i>H</i>-benzo[<i>d</i>]imidazole).

Acta crystallographica. Section E, Crystallographic communications·2025
Same author

Synthesis and crystal structure of 2-(2,4-dioxo-6-methyl-pyran-3-yl-idene)-4-(4-hy-droxy-phen-yl)-2,3,4,5-tetra-hydro-1<i>H</i>-1,5-benzodiazepine.

Acta crystallographica. Section E, Crystallographic communications·2025
Same author

In Silico and in vitro evaluation of the anticancer effect of a 1,5-Benzodiazepin-2-One derivative (3b) revealing potent dual inhibition of HER2 and HDAC1.

Scientific reports·2025

Related Experiment Video

Updated: May 13, 2026

A Direct, Regioselective and Atom-Economical Synthesis of 3-Aroyl-N-hydroxy-5-nitroindoles by Cycloaddition of 4-Nitronitrosobenzene with Alkynones
07:30

A Direct, Regioselective and Atom-Economical Synthesis of 3-Aroyl-N-hydroxy-5-nitroindoles by Cycloaddition of 4-Nitronitrosobenzene with Alkynones

Published on: January 21, 2020

1-Allyl-6-nitro-1H-indazole.

Nabil El Brahmi1, Mohammed Benchidmi, El Mokhtar Essassi

  • 1Laboratoire de Chimie Organique Hétérocyclique URAC21, Faculté des Sciences, Université Mohammed V-Agdal, Avenue Ibn Battouta, BP 1014, Rabat, Morocco.

Acta Crystallographica. Section E, Structure Reports Online
|March 12, 2013
PubMed
Summary

This study details the molecular structure of a novel organic compound, C10H9N3O2. The research reveals its fused ring system, nitro group conformation, and crystal packing via hydrogen bonds.

More Related Videos

Synthesis of Indoxyl-glycosides for Detection of Glycosidase Activities
09:10

Synthesis of Indoxyl-glycosides for Detection of Glycosidase Activities

Published on: May 27, 2015

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 13, 2026

A Direct, Regioselective and Atom-Economical Synthesis of 3-Aroyl-N-hydroxy-5-nitroindoles by Cycloaddition of 4-Nitronitrosobenzene with Alkynones
07:30

A Direct, Regioselective and Atom-Economical Synthesis of 3-Aroyl-N-hydroxy-5-nitroindoles by Cycloaddition of 4-Nitronitrosobenzene with Alkynones

Published on: January 21, 2020

Synthesis of Indoxyl-glycosides for Detection of Glycosidase Activities
09:10

Synthesis of Indoxyl-glycosides for Detection of Glycosidase Activities

Published on: May 27, 2015

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

Area of Science:

  • Crystallography
  • Organic Chemistry
  • Molecular Structure Analysis

Background:

  • Understanding the three-dimensional arrangement of atoms in organic molecules is crucial for predicting their properties and reactivity.
  • Fused heterocyclic systems, such as indazoles, are prevalent in pharmaceuticals and materials science, necessitating detailed structural characterization.

Purpose of the Study:

  • To elucidate the precise molecular geometry and crystal packing of the title compound, C10H9N3O2.
  • To investigate the conformational preferences of the fused ring system, nitro group, and allyl substituent.

Main Methods:

  • Single-crystal X-ray diffraction was employed to determine the atomic coordinates and bond parameters.
  • Analysis of dihedral angles and deviations from mean planes was performed to describe the molecular conformation.
  • Intermolecular interactions, specifically C-H···O hydrogen bonds, were identified and analyzed.

Main Results:

  • The fused five- and six-membered rings of C10H9N3O2 were found to be nearly coplanar.
  • A syn-periplanar conformation was observed between the fused-ring system and the nitro group (dihedral angle 11.34°).
  • The allyl group was oriented nearly perpendicular to the indazole system (dihedral angle 73.3°), and molecules formed tape motifs via C-H···O hydrogen bonds.

Conclusions:

  • The study provides a detailed structural description of C10H9N3O2, highlighting its specific conformational attributes.
  • The identified crystal packing, stabilized by non-classical hydrogen bonds, offers insights into intermolecular forces governing solid-state structure.
  • This structural data serves as a foundation for further investigations into the compound's chemical behavior and potential applications.