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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.
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.
Preparation of 1° Amines: Gabriel Synthesis01:28

Preparation of 1° Amines: Gabriel Synthesis

Direct alkylation is not a suitable method for synthesizing amines because it produces polyalkylated products. Gabriel synthesis is the most preferred method to exclusively make primary amines. The method uses phthalimide, which contains a protected form of nitrogen that participates in alkylation only once to predominantly give primary amines.
Strong bases like NaOH or KOH deprotonate the phthalimide to form the corresponding anion, which acts as a nucleophile. Further, the anion attacks an...
Nomenclature of Carboxylic Acid Derivatives: Amides and Nitriles01:11

Nomenclature of Carboxylic Acid Derivatives: Amides and Nitriles

Naming Amides
The IUPAC and common names of amides are derived from the parent carboxylic acid, by replacing the suffix “oic acid” and “ic acid,” respectively, with “amide.” In the following example, the IUPAC name ethanamide is derived from ethanoic acid, and the common name, acetamide, is obtained from acetic acid.
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.
Preparation of 1° Amines: Hofmann and Curtius Rearrangement Overview01:07

Preparation of 1° Amines: Hofmann and Curtius Rearrangement Overview

In the presence of an aqueous base and a halogen, primary amides can lose the carbonyl (as carbon dioxide) and undergo rearrangement to form primary amines. This reaction, called the Hofmann rearrangement, can produce primary amines (aryl and alkyl) in high yields without contamination by secondary and tertiary amines.

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Related Experiment Video

Updated: Jun 1, 2026

Preparation and Reactivity of a Triphosphenium Bromide Salt: A Convenient and Stable Source of Phosphorus(I)
08:46

Preparation and Reactivity of a Triphosphenium Bromide Salt: A Convenient and Stable Source of Phosphorus(I)

Published on: November 22, 2016

N,N-Bis(diphenyl-phosphanyl)cyclo-propyl-amine.

Ilana Engelbrecht1, Hendrik G Visser, Andreas Roodt

  • 1Department of Chemistry, University of the Free State, PO Box 339, Bloemfontein, 9300, South Africa.

Acta Crystallographica. Section E, Structure Reports Online
|May 19, 2011
PubMed
Summary

This study details the molecular structure of a novel phosphorus-nitrogen compound, C(27)H(25)NP(2). Researchers observed staggered diphenyl-phosphino groups and a near-planar nitrogen atom arrangement, offering insights into chemical bonding.

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Published on: February 7, 2019

Area of Science:

  • Inorganic Chemistry
  • Crystallography
  • Organophosphorus Chemistry

Background:

  • Understanding the structural nuances of organophosphorus compounds is crucial for developing new materials and catalysts.
  • The PNP backbone in coordination chemistry offers unique electronic and steric properties.

Purpose of the Study:

  • To elucidate the precise three-dimensional structure of the title compound, C(27)H(25)NP(2).
  • To analyze the coordination geometry around the nitrogen atom and the orientation of the diphenyl-phosphino groups.

Main Methods:

  • Single-crystal X-ray diffraction was employed to determine the molecular structure.
  • Analysis of bond lengths, bond angles, and dihedral angles provided detailed structural information.

Main Results:

  • The diphenyl-phosphino groups exhibit a staggered conformation relative to the PNP backbone.
  • Dihedral angles between phenyl rings on each phosphorus atom were measured at 51.74(5)° and 68.23(4)°.
  • The nitrogen atom's coordination deviates from trigonal-pyramidal towards an almost planar arrangement with adjacent atoms (N-C/P/P plane distance of 0.098(2) Å).

Conclusions:

  • The compound C(27)H(25)NP(2) possesses a distinct molecular architecture with specific steric arrangements.
  • The near-planar coordination at the nitrogen center suggests potential for unique reactivity or electronic properties.