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Preparation of 1° Amines: Hofmann and Curtius Rearrangement Overview

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.

Diazonium Group Substitution: –OH and –H

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.

IUPAC Nomenclature of Aldehydes

IUPAC Nomenclature of Aldehydes

Aldehydes are named based on the systematic nomenclature rules set by the IUPAC. For acyclic aldehydes, the longest carbon chain containing the aldehydic (–CHO) group is considered the parent chain. The aldehyde is named by replacing the last letter “e” in the hydrocarbon name with “al”. For instance, a simple, seven-carbon-membered acyclic aldehyde is called heptanal, derived from heptane. The carbon chain is numbered starting from the aldehydic carbon, although the aldehydic carbon’s locant...

Nomenclature of Aryl and Heterocyclic Amines

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 Synthesis

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...

Preparation of 1° Amines: Hofmann and Curtius Rearrangement Mechanism

Preparation of 1° Amines: Hofmann and Curtius Rearrangement Mechanism

The Hofmann and Curtius rearrangement reactions can be applied to synthesize primary amines from carboxylic acid derivatives such as amides and acyl azides. In the Hofmann rearrangement, a primary amide undergoes deprotonation in the presence of a base, followed by halogenation to generate an N-haloamide. A second proton abstraction produces a stabilized anionic species, which rearranges to an isocyanate intermediate via an alkyl group migration from the carbonyl carbon to the neighboring...

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Updated: Jun 1, 2026

Modification and Functionalization of the Guanidine Group by Tailor-made Precursors

Modification and Functionalization of the Guanidine Group by Tailor-made Precursors

Published on: April 27, 2017

1-(3-Phenyl-prop-yl)urea.

Yang Li¹, Guoxiong Hua, Alexandra M Z Slawin

¹School of Chemistry, University of St Andrews, Fife KY16 9ST, Scotland.

Acta Crystallographica. Section E, Structure Reports Online

|May 18, 2011

Summary

This summary is machine-generated.

This study reveals the crystal structure of a compound featuring double supramolecular layers. These layers are formed through intermolecular hydrogen bonding, creating specific structural motifs.

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Area of Science:

Crystal Engineering
Supramolecular Chemistry
Organic Chemistry

Background:

Understanding crystal packing is crucial for designing materials with specific properties.
Hydrogen bonding plays a key role in the self-assembly of molecules in the solid state.

Purpose of the Study:

To elucidate the crystal structure of the title compound, C(10)H(14)N(2)O.
To investigate the intermolecular interactions and supramolecular assembly in the crystal.

Main Methods:

Single-crystal X-ray diffraction analysis was employed to determine the molecular and crystal structure.
Analysis of hydrogen bonding networks and their associated motifs (e.g., R(2)(8), R(2)(1)(6)).

Main Results:

The crystal structure exhibits double supramolecular layers parallel to the bc plane.
Intermolecular N-H⋯O hydrogen bonding dictates the layer formation.
Specific hydrogen bonding motifs, R(2)(2)(8) and R(2)(1)(6), were identified along the b- and c-axis directions.
A significant dihedral angle of 84.8(2)° was observed between the benzene ring and the C(ar)-C-C group mean plane.

Conclusions:

The study provides detailed insights into the supramolecular architecture of the title compound.
The identified hydrogen bonding patterns and structural motifs are fundamental to understanding its solid-state behavior.
The conformational details, including the dihedral angle, contribute to the overall crystal packing.