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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.

Structure of Amines

Structure of Amines

The hybridized nitrogen atom in amines possesses a lone pair of electrons and is bound to three substituents with a bond angle of around 108°, which is less than the tetrahedral angle of 109.5°. However, the C–N–H bond angle is slightly larger at 112°, with a carbon–nitrogen bond length of 147 pm. This carbon–nitrogen bond length of of amines is longer than the carbon–oxygen bond of alcohols (143 pm) but shorter than alkanes’ carbon–carbon bond (154 pm). These aspects are illustrated in Figure...

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...

Ionic Crystal Structures

Ionic Crystal Structures

Ionic crystals consist of two or more different kinds of ions that usually have different sizes. The packing of these ions into a crystal structure is more complex than the packing of metal atoms that are the same size.
Most monatomic ions behave as charged spheres, and their attraction for ions of opposite charge is the same in every direction. Consequently, stable structures for ionic compounds result (1) when ions of one charge are surrounded by as many ions as possible of the opposite...

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.

Nomenclature of Secondary and Tertiary Amines

Nomenclature of Secondary and Tertiary Amines

The secondary and tertiary amines are derivatives of ammonia, where two and three of its hydrogens are replaced by alkyl groups, respectively. Secondary and tertiary amines can be symmetrical with identical alkyl groups attached to the nitrogen atom or unsymmetrical when more than one type of alkyl group is present. The standard nomenclature of secondary and tertiary amines is similar to the names given to the primary amines. They are generally named alkylamines. As depicted in Figure 1, for...

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1,3-Bis(2-chloro-phen-yl)thio-urea: a monoclinic polymorph.

Chien Ing Yeo¹, Edward R T Tiekink

¹Department of Chemistry, University of Malaya, 50603 Kuala Lumpur, Malaysia.

Acta Crystallographica. Section E, Structure Reports Online

|January 6, 2012

Summary

This study describes a new monoclinic polymorph of a C(13)H(10)Cl(2)N(2)S compound. The molecular structure features twisted benzene rings and specific hydrogen bonding arrangements in its crystal lattice.

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Area of Science:

Crystallography
Solid-state chemistry
Materials science

Background:

The title compound, C(13)H(10)Cl(2)N(2)S, exists in multiple crystalline forms.
Polymorphism significantly impacts material properties.

Purpose of the Study:

To characterize a novel monoclinic polymorph of C(13)H(10)Cl(2)N(2)S.
To elucidate the crystal structure and intermolecular interactions of this new form.

Main Methods:

Single-crystal X-ray diffraction was employed to determine the crystal structure.
Analysis of bond lengths, bond angles, and intermolecular interactions (hydrogen bonds, van der Waals forces).

Main Results:

The compound crystallizes as a monoclinic polymorph, distinct from the previously reported ortho-rhom-bic form.
The molecule exhibits a twisted conformation with a dihedral angle of 55.37° between benzene rings.
N-H atoms are in a syn configuration, differing from the anti configuration in the ortho-rhom-bic form.
Crystal packing involves zigzag chains formed by N-H⋯S hydrogen bonds along the c-axis.
Chains are further organized into layers through C-H⋯Cl interactions, stacking along the a-axis.

Conclusions:

A new monoclinic polymorph of C(13)H(10)Cl(2)N(2)S has been identified and structurally characterized.
The conformational differences and crystal packing highlight the nuances of polymorphism in this compound.
Understanding these structural variations is crucial for predicting and controlling material properties.