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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.
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.
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.
Physical Properties of Amines01:26

Physical Properties of Amines

Amines with low molecular weight are usually gaseous at room temperature, while those with high molecular weight are liquid or solids in nature. Usually, low molecular weight amines have a rotten fish-like smell. Diamines typically have a pungent smell. For instance, cadaverine and putrescine, depicted in Figure 1, are two molecules responsible for decaying tissue.
Basicity of Aromatic Amines01:18

Basicity of Aromatic Amines

The basicity of aromatic amines is much weaker than that of aliphatic amines due to the involvement of the lone pair of electrons over the N atom in resonance with the aryl rings. Generally, the electron-donating ability of any substituents on the aryl ring of aromatic amines increases the basicity of the amine by increasing electron density, and hence the availability of lone pair on the nitrogen. On the other hand, electron-withdrawing functional groups on the aryl ring of amines decrease the...

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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

4-Nitro-N-[(E)-thio-phen-2-yl-methyl-idene]aniline.

Abdullah M Asiri, Hassan M Faidallah, Seik Weng Ng

    Acta Crystallographica. Section E, Structure Reports Online
    |July 17, 2012
    PubMed
    Summary

    This study details the molecular structure of C(11)H(8)N(2)O(2)S, revealing significant twists between its ring systems. Crystal analysis shows layered structures formed by intermolecular interactions and connected by pi-pi stacking.

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    Synthesis of Antiviral Tetrahydrocarbazole Derivatives by Photochemical and Acid-catalyzed C-H Functionalization via Intermediate Peroxides (CHIPS)
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    Published on: June 20, 2014

    Area of Science:

    • Crystallography
    • Organic Chemistry
    • Supramolecular Chemistry

    Background:

    • Understanding molecular conformation is crucial for predicting chemical and physical properties.
    • Intermolecular interactions dictate crystal packing and material properties.

    Purpose of the Study:

    • To elucidate the three-dimensional molecular structure and crystal packing of the title compound C(11)H(8)N(2)O(2)S.
    • To investigate the nature of intermolecular interactions driving the supramolecular assembly in the solid state.

    Main Methods:

    • Single-crystal X-ray diffraction was employed to determine the molecular geometry and crystal structure.
    • Analysis of bond lengths, bond angles, and torsion angles provided insights into molecular conformation.
    • Intermolecular interactions, including hydrogen bonds and pi-pi stacking, were identified and analyzed.

    Main Results:

    • The molecule exhibits a notable twist (31.77°) between its five- and six-membered rings.
    • The nitro group is slightly distorted from the plane of the attached benzene ring (torsion angle 9.0°).
    • Supramolecular layers are formed via C-H···O and C-H···N interactions, further organized into a 3D architecture by pi-pi stacking of benzene rings (3.6020 Å centroid-centroid distance).

    Conclusions:

    • The crystal structure of C(11)H(8)N(2)O(2)S is characterized by significant intramolecular conformational flexibility.
    • The compound self-assembles into a layered supramolecular structure driven by a combination of hydrogen bonding and pi-pi interactions.
    • These findings contribute to the understanding of structure-property relationships in organic crystalline materials.