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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.
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 Primary Amines01:17

Nomenclature of Primary Amines

Primary, secondary, and tertiary amines are compounds consisting of one, two, and three alkyl groups connected to the amino group (–NH2), respectively. As depicted in Figure 1, the common name of the primary amines is obtained by adding the suffix -amine to the alkyl substituent attached to the amino group as the corresponding alkylamine.
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...
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.
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...

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Related Experiment Video

Updated: May 27, 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

(E)-N-[(6-Bromo-pyridin-2-yl)methyl-idene]-4-methyl-aniline.

Mingjian Cai, Penggao Ma, Xiuge Wang

    Acta Crystallographica. Section E, Structure Reports Online
    |November 8, 2011
    PubMed
    Summary

    This study details a novel Schiff base, C(13)H(11)BrN(2), synthesized from 6-bromo-picolinaldehyde and p-toluidine. The compound exhibits an E configuration around the C=N bond, with a specific dihedral angle between its aromatic rings.

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    Published on: November 23, 2016

    Area of Science:

    • Organic Chemistry
    • Crystallography
    • Molecular Structure

    Background:

    • Schiff bases are versatile organic compounds with diverse applications.
    • Understanding the structural properties of Schiff bases is crucial for their targeted synthesis and application.
    • The specific combination of 6-bromo-picolinaldehyde and p-toluidine presents an interesting case for structural investigation.

    Purpose of the Study:

    • To synthesize and characterize a novel Schiff base derived from 6-bromo-picolinaldehyde and p-toluidine.
    • To determine the stereochemistry and conformational properties of the synthesized compound.
    • To elucidate the dihedral angle between the aromatic rings in the title compound.

    Main Methods:

    • Chemical synthesis involving the condensation of an aldehyde and an amine.
    • Spectroscopic analysis (e.g., NMR, IR) for structural confirmation.
    • Single-crystal X-ray diffraction to determine the precise molecular geometry and conformation.

    Main Results:

    • Successful synthesis of the Schiff base C(13)H(11)BrN(2).
    • Confirmation of the E configuration about the carbon-nitrogen (C=N) double bond.
    • Determination of a dihedral angle of 30.4(1)° between the benzene and pyridine rings.

    Conclusions:

    • The synthesized Schiff base possesses a defined E configuration and a specific spatial arrangement of its aromatic systems.
    • The structural data provides fundamental insights into the molecular architecture of this class of compounds.
    • This work contributes to the growing body of knowledge on Schiff base chemistry and crystallography.