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Related Concept Videos

Physical Properties of Amines01:26

Physical Properties of Amines

Amines with low molecular weight are usually gaseous at room temperature, while those with high molecular weight are liquid or solids in nature. Usually, low molecular weight amines have a rotten fish-like smell. Diamines typically have a pungent smell. For instance, cadaverine and putrescine, depicted in Figure 1, are two molecules responsible for decaying tissue.
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.
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.
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...
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...
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.

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Related Experiment Video

Updated: Jun 5, 2026

Color Spot Test As a Presumptive Tool for the Rapid Detection of Synthetic Cathinones
06:06

Color Spot Test As a Presumptive Tool for the Rapid Detection of Synthetic Cathinones

Published on: February 5, 2018

8-Bromo-naphthalen-1-amine.

Amy L Fuller1, Fergus R Knight, Alexandra M Z Slawin

  • 1Department of Chemistry, University of St Andrews, St Andrews KY16 9ST, Scotland.

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

Researchers synthesized a novel brominated naphthalene compound. This molecule exhibits reduced steric strain and unique hydrogen bonding, with a distinct herring-bone crystal structure.

Area of Science:

  • Organic Chemistry
  • Crystallography
  • Supramolecular Chemistry

Background:

  • 1,8-disubstituted naphthalene compounds often exhibit significant steric strain.
  • Understanding the structural and bonding properties of novel naphthalene derivatives is crucial for materials science.

Purpose of the Study:

  • To synthesize and characterize a new 1,8-disubstituted naphthalene compound.
  • To investigate the steric and hydrogen bonding characteristics of the synthesized molecule.
  • To determine the crystal packing arrangement of the compound.

Main Methods:

  • Synthesis via reaction of 8-bromo-1-naphthoic acid with sodium azide and aqueous ammonia.
  • Purification by crystallization from petroleum ether.
  • Structural analysis inferred from the observed properties and bonding.

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Microwave-assisted Intramolecular Dehydrogenative Diels-Alder Reactions for the Synthesis of Functionalized Naphthalenes/Solvatochromic Dyes
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Microwave-assisted Intramolecular Dehydrogenative Diels-Alder Reactions for the Synthesis of Functionalized Naphthalenes/Solvatochromic Dyes

Published on: April 1, 2013

Qualitative Identification of Carboxylic Acids, Boronic Acids, and Amines Using Cruciform Fluorophores
09:46

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

Published on: August 19, 2013

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Color Spot Test As a Presumptive Tool for the Rapid Detection of Synthetic Cathinones
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Color Spot Test As a Presumptive Tool for the Rapid Detection of Synthetic Cathinones

Published on: February 5, 2018

Microwave-assisted Intramolecular Dehydrogenative Diels-Alder Reactions for the Synthesis of Functionalized Naphthalenes/Solvatochromic Dyes
12:07

Microwave-assisted Intramolecular Dehydrogenative Diels-Alder Reactions for the Synthesis of Functionalized Naphthalenes/Solvatochromic Dyes

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Qualitative Identification of Carboxylic Acids, Boronic Acids, and Amines Using Cruciform Fluorophores
09:46

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

Published on: August 19, 2013

Main Results:

  • A novel compound, C(10)H(8)BrN, was successfully synthesized and isolated as pink crystals.
  • The compound displays reduced steric strain between the 1 and 8 substituents compared to related naphthalene derivatives.
  • Intra- and inter-molecular hydrogen bonds involving NH protons were identified.
  • Naphthalene units adopt a herring-bone stacking motif in the crystal lattice.

Conclusions:

  • The synthesized brominated naphthalene derivative exhibits unique structural features, including reduced strain and specific hydrogen bonding.
  • The herring-bone stacking arrangement suggests potential for interesting solid-state properties.
  • This study contributes to the understanding of structure-property relationships in sterically hindered naphthalene systems.