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Related Concept Videos

Basicity of Heterocyclic Aromatic Amines01:25

Basicity of Heterocyclic Aromatic Amines

Heterocyclic amines, where the N atom is a part of an alicyclic system, are similar in basicity to alkylamines. Interestingly, the heterocyclic amine having a nitrogen atom as part of an aromatic ring has much less basicity than its corresponding alicyclic counterpart. For this reason, as presented in Figure 1, piperidine (pKb = 2.8) is significantly more basic than pyridine (pKb = 8.8).
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 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.
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.
Five-Membered Heterocyclic Aromatic Compounds: Overview01:13

Five-Membered Heterocyclic Aromatic Compounds: Overview

Heterocyclic aromatic compounds are cyclic compounds that are aromatic and have one or more heteroatoms—atoms other than carbon, in the ring. Depending upon the number of atoms present in the ring, they can be either five or six-membered. Examples of five-membered heterocyclic aromatic compounds include pyrrole, furan, thiophene, and imidazole. Pyrrole consists of one nitrogen atom having one lone pair of electrons. Furan and thiophene have one oxygen and one sulfur heteroatom, respectively.
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 2, 2026

Microwave-Assisted Preparation of 1-Aryl-1H-pyrazole-5-amines
05:07

Microwave-Assisted Preparation of 1-Aryl-1H-pyrazole-5-amines

Published on: June 23, 2019

N-Nitro-1H-pyrrole-2-carboxamide.

Long Liu, Chunlin He, Zengxi Li

    Acta Crystallographica. Section E, Structure Reports Online
    |April 28, 2011
    PubMed
    Summary

    This study details the crystal structure of a nitroamide compound, C(5)H(5)N(3)O(3). Molecular analysis reveals specific torsion angles and intermolecular hydrogen bonding that form layered crystal structures.

    Area of Science:

    • Crystallography
    • Organic Chemistry
    • Materials Science

    Background:

    • Understanding molecular arrangements is key to predicting material properties.
    • Nitroamide compounds exhibit diverse structural motifs and intermolecular interactions.
    • Crystal engineering relies on precise characterization of molecular packing.

    Purpose of the Study:

    • To elucidate the crystal structure of the title compound, C(5)H(5)N(3)O(3).
    • To analyze the conformational preferences and intermolecular interactions within the crystal lattice.
    • To describe the supramolecular assembly and resulting motifs.

    Main Methods:

    • Single-crystal X-ray diffraction was employed to determine the molecular and crystal structure.
    • Analysis of C-N-N-O torsion angles provided insights into conformational preferences.

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    A General Method for Detecting Nitrosamide Formation in the In Vitro Metabolism of Nitrosamines by Cytochrome P450s
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    A General Method for Detecting Nitrosamide Formation in the In Vitro Metabolism of Nitrosamines by Cytochrome P450s

    Published on: September 25, 2017

    Rapid Scan Electron Paramagnetic Resonance Opens New Avenues for Imaging Physiologically Important Parameters In Vivo
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    Rapid Scan Electron Paramagnetic Resonance Opens New Avenues for Imaging Physiologically Important Parameters In Vivo

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    Microwave-Assisted Preparation of 1-Aryl-1H-pyrazole-5-amines
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    Published on: June 23, 2019

    A General Method for Detecting Nitrosamide Formation in the In Vitro Metabolism of Nitrosamines by Cytochrome P450s
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    A General Method for Detecting Nitrosamide Formation in the In Vitro Metabolism of Nitrosamines by Cytochrome P450s

    Published on: September 25, 2017

    Rapid Scan Electron Paramagnetic Resonance Opens New Avenues for Imaging Physiologically Important Parameters In Vivo
    08:01

    Rapid Scan Electron Paramagnetic Resonance Opens New Avenues for Imaging Physiologically Important Parameters In Vivo

    Published on: September 26, 2016

  • Identification and analysis of intermolecular hydrogen bonds (N-H⋯O, C-H⋯O) were performed.

    • Main Results:

    • The nitro group is twisted relative to the amide group, with specific torsion angles (29.0(2)° and -153.66(14)°).
    • Molecules self-assemble via intermolecular N-H⋯O and C-H⋯O hydrogen bonds.
    • These interactions lead to the formation of supramolecular chains along the a axis, which stack into layers in the (001) plane.

    Conclusions:

    • The crystal structure of C(5)H(5)N(3)O(3) is characterized by a non-planar arrangement of the nitro and amide groups.
    • Intermolecular hydrogen bonding dictates the formation of one-dimensional chains and two-dimensional layer motifs.
    • This detailed structural analysis provides a foundation for understanding structure-property relationships in related nitroamide compounds.