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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.
ortho–para-Directing Activators: –CH3, –OH, –⁠NH2, –OCH301:11

ortho–para-Directing Activators: –CH3, –OH, –⁠NH2, –OCH3

All ortho–para directors, excluding halogens, are activating groups. These groups donate electrons to the ring, making the ring carbons electron-rich. Consequently, the reactivity of the aromatic ring towards electrophilic substitution increases. For instance, the nitration of anisole is about 10,000 times faster than the nitration of benzene. The electron-donating effect of the methoxy group in anisole activates the ortho and para positions on the ring and stabilizes the corresponding...
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.
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.
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.
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.

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Related Experiment Video

Updated: Jun 1, 2026

A Direct, Regioselective and Atom-Economical Synthesis of 3-Aroyl-N-hydroxy-5-nitroindoles by Cycloaddition of 4-Nitronitrosobenzene with Alkynones
07:30

A Direct, Regioselective and Atom-Economical Synthesis of 3-Aroyl-N-hydroxy-5-nitroindoles by Cycloaddition of 4-Nitronitrosobenzene with Alkynones

Published on: January 21, 2020

4-[3-(4-Nitro-phen-oxy)prop-oxy]aniline.

Li-Mei Zheng, Xian Wei, Xiao-Rong Peng

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

    This study reveals how molecules of C(15)H(16)N(2)O(4) self-assemble. Hydrogen bonds create chains, while weaker interactions form a 3D crystal structure.

    Area of Science:

    • Crystal Engineering
    • Supramolecular Chemistry
    • Materials Science

    Background:

    • Understanding intermolecular forces is crucial for designing novel materials.
    • Crystal structure analysis provides insights into molecular assembly.
    • Hydrogen bonds and C-H···π interactions are key non-covalent forces in crystal packing.

    Purpose of the Study:

    • To elucidate the crystal structure of the title compound C(15)H(16)N(2)O(4).
    • To investigate the role of hydrogen bonding and C-H···π interactions in the compound's self-assembly.
    • To characterize the resulting one-dimensional and three-dimensional network structures.

    Main Methods:

    • Single-crystal X-ray diffraction was employed to determine the molecular and crystal structure.
    • Analysis of intermolecular interactions, including hydrogen bonds (N-H⋯O) and C-H⋯π interactions, was performed.

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    Synthesis of Antiviral Tetrahydrocarbazole Derivatives by Photochemical and Acid-catalyzed C-H Functionalization via Intermediate Peroxides (CHIPS)

    Published on: June 20, 2014

  • Structural visualization tools were used to illustrate the formation of chains and the 3D network.

    • Main Results:

    • The crystal structure of C(15)H(16)N(2)O(4) was successfully determined.
    • Molecules are organized into undulating one-dimensional chains through N-H⋯O hydrogen bonds.
    • Adjacent chains are interconnected by weak C-H⋯π interactions, leading to a stable three-dimensional network.

    Conclusions:

    • The crystal packing of C(15)H(16)N(2)O(4) is governed by a combination of strong hydrogen bonds and weaker C-H⋯π interactions.
    • These interactions dictate the formation of a robust 1D chain and a 3D supramolecular network.
    • The findings contribute to the understanding of crystal engineering principles for designing functional molecular materials.