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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.
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...
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.
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...
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...

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Related Experiment Video

Updated: May 20, 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

Dicyclo-hexyl-ammonium 3,5-dinitro-benzoate.

Sohail Saeed, Naghmana Rashid, Rizwan Hussain

    Acta Crystallographica. Section E, Structure Reports Online
    |July 17, 2012
    PubMed
    Summary

    This study details the crystal structure of a salt, revealing hydrogen bonds and π-π stacking interactions. These molecular arrangements form specific ring structures within the crystal lattice.

    Area of Science:

    • Crystallography
    • Supramolecular Chemistry
    • Chemical Physics

    Background:

    • Understanding the intermolecular forces governing crystal packing is crucial for materials science.
    • Hydrogen bonding and π-π stacking are key non-covalent interactions that dictate molecular assembly.
    • The specific salt, C(12)H(24)N(+)·C(7)H(3)N(2)O(6) (-), was chosen for detailed structural analysis.

    Purpose of the Study:

    • To elucidate the crystal structure of the title salt.
    • To identify and characterize the intermolecular interactions present in the crystal lattice.
    • To analyze the resulting supramolecular architecture.

    Main Methods:

    • Single-crystal X-ray diffraction was employed to determine the crystal structure.
    • Analysis of hydrogen bonding networks using N-H⋯O interactions.

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    A Direct, Early Stage Guanidinylation Protocol for the Synthesis of Complex Aminoguanidine-containing Natural Products
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    A Direct, Early Stage Guanidinylation Protocol for the Synthesis of Complex Aminoguanidine-containing Natural Products

    Published on: September 9, 2016

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

    Published on: August 22, 2018

    Qualitative Identification of Carboxylic Acids, Boronic Acids, and Amines Using Cruciform Fluorophores
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    Qualitative Identification of Carboxylic Acids, Boronic Acids, and Amines Using Cruciform Fluorophores

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    A Direct, Early Stage Guanidinylation Protocol for the Synthesis of Complex Aminoguanidine-containing Natural Products
    09:04

    A Direct, Early Stage Guanidinylation Protocol for the Synthesis of Complex Aminoguanidine-containing Natural Products

    Published on: September 9, 2016

  • Investigation of π-π stacking between aromatic rings.

    • Main Results:

    • The asymmetric unit contains two cations and two anions.
    • A 12-membered ring motif (R(4)(4)(12)) was identified, formed by N-H⋯O hydrogen bonds between cations and anions.
    • The crystal structure exhibits π-π stacking between parallel benzene rings with a centroid-centroid distance of 3.771(2) Å.
    • An inversion center is located at the center of the 12-membered ring.

    Conclusions:

    • The crystal structure is stabilized by a combination of hydrogen bonding and π-π stacking.
    • The observed supramolecular arrangement leads to the formation of a specific 12-membered ring system.
    • This detailed structural information contributes to the understanding of molecular self-assembly in crystalline solids.