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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.
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...
Radical Substitution: Allylic Bromination01:27

Radical Substitution: Allylic Bromination

In organic synthesis, the formation of products can be altered by changing the reaction conditions. For example, a dibromo addition product is formed when propene is treated with bromine at room temperature. In contrast, propene undergoes allylic substitution in non-polar solvents at high temperatures to give 3-bromopropene. In order to avoid the addition reaction, the bromine concentration must be kept as low as possible throughout the reaction. This can be achieved using N-bromosuccinimide...
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.
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.
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.

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Related Experiment Video

Updated: May 26, 2026

One-pot Microwave-assisted Conversion of Anomeric Nitrate-esters to Trichloroacetimidates
06:00

One-pot Microwave-assisted Conversion of Anomeric Nitrate-esters to Trichloroacetimidates

Published on: January 15, 2018

2-Nitro-anilinium bromide.

R Anitha, S Athimoolam, S Asath Bahadur

    Acta Crystallographica. Section E, Structure Reports Online
    |January 6, 2012
    PubMed
    Summary
    This summary is machine-generated.

    This study details the crystal structure of a novel compound, revealing intramolecular hydrogen bonds and zigzag chains. These structures form layered arrangements of hydrophilic and hydrophobic regions.

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    Low Pressure Vapor-assisted Solution Process for Tunable Band Gap Pinhole-free Methylammonium Lead Halide Perovskite Films
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    Low Pressure Vapor-assisted Solution Process for Tunable Band Gap Pinhole-free Methylammonium Lead Halide Perovskite Films

    Published on: September 8, 2017

    Area of Science:

    • Crystal chemistry
    • Supramolecular chemistry
    • Organic chemistry

    Background:

    • The title compound, C(6)H(7)N(2)O(2) (+)·Br(-), shares structural similarities with 2-nitro-anilinium chloride.
    • Understanding hydrogen bonding and crystal packing is crucial for predicting material properties.

    Purpose of the Study:

    • To elucidate the crystal structure of the title compound.
    • To identify and characterize hydrogen bonding interactions and supramolecular motifs.
    • To describe the arrangement of hydrophilic and hydrophobic layers in the crystal lattice.

    Main Methods:

    • Single-crystal X-ray diffraction analysis was employed to determine the crystal structure.
    • Analysis of hydrogen bonding networks, including intra- and inter-molecular interactions.
    • Identification of characteristic supramolecular motifs (e.g., S(6), C(2)(1)(4), R(6)(3)(12)).

    Main Results:

    • The compound exhibits an intramolecular N-H⋯O hydrogen bond, forming an S(6) motif.
    • Intermolecular N-H⋯Br hydrogen bonds are present, contributing to the crystal architecture.
    • Zigzag chains (C(2)(1)(4) motifs) extend along the b-axis, intersecting to form double helix-like structures.
    • These structures result in R(6)(3)(12) ring motifs arranged sequentially along the b-axis.
    • A layered structure is formed with alternating hydrophilic and hydrophobic regions.

    Conclusions:

    • The crystal structure is characterized by specific hydrogen bonding patterns and supramolecular assemblies.
    • The arrangement of motifs leads to a unique layered organization of the compound.
    • This structural insight provides a foundation for further studies on related compounds and their properties.