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Related Concept Videos

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.
Structure of Amines01:19

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 Mechanism01:26

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...
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.
Radicals: Electronic Structure and Geometry01:07

Radicals: Electronic Structure and Geometry

This lesson delves into the geometry of a radical, which is influenced by the electronic structure of the molecule. The principle is similar to that of a lone pair, where the unpaired electron influences the geometry at the radical center.
Accordingly, the structure of a trivalent radical lies between the geometries of carbocations and carbanions. An sp2-hybridized carbocation is trigonal planar, while an sp3-hybridized carbanion is trigonal pyramidal. Here, the difference in geometry is...
Structures of Solids02:22

Structures of Solids

Solids in which the atoms, ions, or molecules are arranged in a definite repeating pattern are known as crystalline solids. Metals and ionic compounds typically form ordered, crystalline solids. A crystalline solid has a precise melting temperature because each atom or molecule of the same type is held in place with the same forces or energy. Amorphous solids or non-crystalline solids (or, sometimes, glasses) which lack an ordered internal structure and are randomly arranged. Substances that...

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Related Experiment Video

Updated: Jun 1, 2026

Construction and Systematical Symmetric Studies of a Series of Supramolecular Clusters with Binary or Ternary Ammonium Triphenylacetates
06:35

Construction and Systematical Symmetric Studies of a Series of Supramolecular Clusters with Binary or Ternary Ammonium Triphenylacetates

Published on: February 15, 2016

1,3-Bis(3-methyl-phen-yl)thio-urea: triclinic polymorph.

Durre Shahwar, M Nawaz Tahir, Muhammad Akmal Khan

    Acta Crystallographica. Section E, Structure Reports Online
    |May 18, 2011
    PubMed
    Summary

    This study details the crystal structure of a C(15)H(16)N(2)S compound, revealing distinct crystallographic behaviors between its isomers. Dimerization occurs through specific hydrogen bonds, forming characteristic ring motifs and exhibiting varied benzene ring dihedral angles.

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    Construction and Systematical Symmetric Studies of a Series of Supramolecular Clusters with Binary or Ternary Ammonium Triphenylacetates
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    One-pot Microwave-assisted Conversion of Anomeric Nitrate-esters to Trichloroacetimidates

    Published on: January 15, 2018

    Area of Science:

    • Crystal Engineering
    • Supramolecular Chemistry
    • Organic Crystallography

    Background:

    • Understanding the solid-state behavior of organic molecules is crucial for materials science.
    • Hydrogen bonding interactions play a significant role in molecular self-assembly and crystal packing.
    • Isomeric compounds can exhibit distinct crystallographic properties influencing their physical characteristics.

    Purpose of the Study:

    • To elucidate the crystal structure and intermolecular interactions of the title compound C(15)H(16)N(2)S.
    • To investigate the crystallographic differences between the two isomers present in the asymmetric unit.
    • To characterize the hydrogen bonding motifs and conformational preferences within the crystal lattice.

    Main Methods:

    • Single-crystal X-ray diffraction analysis was employed to determine the three-dimensional structure.
    • Analysis of intermolecular interactions, including N-H⋯S and C-H⋯S hydrogen bonds.
    • Determination of dihedral angles between aromatic rings and assessment of atomic disorder.

    Main Results:

    • The title compound, C(15)H(16)N(2)S, crystallizes with two molecules in the asymmetric unit, displaying different crystallographic behaviors.
    • Intermolecular N-H⋯S hydrogen bonds facilitate dimerization, forming R(2)(2)(8) ring motifs.
    • C-H⋯S hydrogen bonds contribute to R(2)(2)(12) ring motifs, with varied dihedral angles (62.54° and 79.54°) between benzene rings in the two molecules.
    • Disorder in methyl group hydrogen atoms was observed in both molecules with specific occupancy ratios.

    Conclusions:

    • The crystal structure reveals specific hydrogen bonding patterns dictating the self-assembly of the C(15)H(16)N(2)S isomers.
    • The observed dimerization and varied dihedral angles highlight the conformational flexibility and packing preferences of the molecule.
    • Understanding these crystallographic details provides insights into structure-property relationships for related organic compounds.