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Related Concept Videos

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.
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.
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.
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.
Amines to Amides: Acylation of Amines01:19

Amines to Amides: Acylation of Amines

Various carboxylic acid derivatives (such as acid chlorides, esters, and anhydrides) can be used for the acylation of amines to yield amides. The reaction requires two equivalents of amines. The first amine molecule functions as a nucleophile and attacks the carbonyl carbon to produce a tetrahedral intermediate. This is followed by the loss of the leaving group and restoration of the C=O bond.
Next, the second equivalent of amine serves as a Brønsted base and deprotonates the quaternary amide...
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...

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Related Experiment Video

Updated: Jun 5, 2026

Protocol for the Synthesis of Ortho-trifluoromethoxylated Aniline Derivatives
08:43

Protocol for the Synthesis of Ortho-trifluoromethoxylated Aniline Derivatives

Published on: January 19, 2016

4-Bromo-2,6-dimethyl-aniline.

Rui Liu1, Yu-Hao Li, Wei Luo

  • 1Department of Applied Chemistry, College of Science, Nanjing University of Technology, Nanjing 210009, People's Republic of China.

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

This study details the crystal structure of a bromine-containing organic compound. Independent molecules within the crystal are linked by hydrogen bonds, revealing insights into molecular arrangement.

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Area of Science:

  • Crystallography
  • Organic Chemistry
  • Solid-State Chemistry

Background:

  • Understanding the arrangement of atoms in organic compounds is crucial for predicting their properties.
  • Crystal structure analysis provides detailed information about molecular conformation and intermolecular interactions.
  • The title compound, C(8)H(10)BrN, is a novel organic molecule whose solid-state behavior warrants investigation.

Purpose of the Study:

  • To determine the crystal structure of the title compound, C(8)H(10)BrN.
  • To analyze the molecular geometry and identify intermolecular interactions within the crystal lattice.
  • To provide a foundation for further studies on the physical and chemical properties of this compound.

Main Methods:

  • Single-crystal X-ray diffraction was employed to collect diffraction data.
  • The crystal structure was solved and refined using standard crystallographic software.
  • Analysis of bond lengths, bond angles, and intermolecular contacts was performed.

Main Results:

  • The asymmetric unit contains two independent molecules of C(8)H(10)BrN.
  • The bromine, nitrogen, and methyl group carbon atoms are coplanar with the benzene ring.
  • N-H⋯N hydrogen bonds were identified as the primary intermolecular forces linking the molecules in the crystal structure.

Conclusions:

  • The crystal structure of C(8)H(10)BrN has been successfully elucidated.
  • The presence of specific hydrogen bonding interactions dictates the observed packing in the solid state.
  • This structural information is vital for understanding the compound's reactivity and potential applications.