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Related Concept Videos

Electrophilic Aromatic Substitution: Nitration of Benzene01:20

Electrophilic Aromatic Substitution: Nitration of Benzene

The nitration of benzene is an example of an electrophilic aromatic substitution reaction. It involves the formation of a very powerful electrophile, the nitronium ion, which is linear in shape. The reaction occurs through the interaction of two strong acids, sulfuric and nitric acid.
meta-Directing Deactivators: –NO2, –CN, –CHO, –⁠CO2R, –COR, –CO2H01:13

meta-Directing Deactivators: –NO2, –CN, –CHO, –⁠CO2R, –COR, –CO2H

All meta-directing substituents are deactivating groups. These substituents withdraw electrons from the aromatic ring, making the ring less reactive toward electrophilic substitution. For example, the nitration of nitrobenzene is 100,000 times slower than that of benzene because of the deactivating effect of the nitro group. The first step in an electrophilic aromatic substitution is the addition of an electrophile to form a resonance-stabilized carbocation. The energy diagrams for the...
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.
NMR Spectroscopy of Benzene Derivatives01:37

NMR Spectroscopy of Benzene Derivatives

Simple unsubstituted benzene has six aromatic protons, all chemically equivalent. Therefore, benzene exhibits only a singlet peak at δ 7.3 ppm in the 1H NMR spectrum. The observed shift is far downfield because the aromatic ring current strongly deshields the protons. Any substitution on the benzene ring makes the aromatic protons nonequivalent, and the protons split each other. The peak is, therefore, no longer a singlet and the splitting pattern and their associated coupling constants depend...
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.

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Related Experiment Video

Updated: Jun 5, 2026

A General Method for Detecting Nitrosamide Formation in the In Vitro Metabolism of Nitrosamines by Cytochrome P450s
07:38

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

Published on: September 25, 2017

N-(2-Methoxy-phen-yl)-2-nitro-benzamide.

Aamer Saeed, Shahid Hussain, Michael Bolte

    Acta Crystallographica. Section E, Structure Reports Online
    |January 5, 2011
    PubMed
    Summary

    This study details the molecular geometry of C(14)H(12)N(2)O(4), revealing specific dihedral angles between aromatic rings and nitro group twists. Crystal structure analysis confirmed stabilization through an N-H⋯O hydrogen bond.

    Area of Science:

    • Crystallography
    • Organic Chemistry
    • Molecular Structure Analysis

    Background:

    • Understanding the precise three-dimensional arrangement of atoms in organic molecules is crucial for predicting their properties and reactivity.
    • The specific compound C(14)H(12)N(2)O(4) presents an interesting case for structural investigation due to its aromatic and nitro functionalities.

    Purpose of the Study:

    • To determine the detailed geometric parameters of the title compound, C(14)H(12)N(2)O(4).
    • To elucidate the spatial relationship between the two aromatic rings and the orientation of the nitro group.
    • To identify the intermolecular interactions stabilizing the crystal structure.

    Main Methods:

    • Single-crystal X-ray diffraction was employed to analyze the crystal structure.
    • Geometric parameters, including bond lengths, bond angles, and dihedral angles, were precisely measured.

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  • Hydrogen bonding interactions were identified through crystallographic analysis.
  • Main Results:

    • The geometric parameters of C(14)H(12)N(2)O(4) were found to be within expected ranges for similar organic structures.
    • A significant dihedral angle of 28.9(1)° was observed between the two aromatic rings.
    • The nitro group exhibited a notable twist of 40.2(1)° relative to its attached aromatic ring.

    Conclusions:

    • The determined molecular geometry provides a fundamental understanding of C(14)H(12)N(2)O(4)'s structure.
    • The observed dihedral angles and nitro group twist highlight specific conformational preferences of the molecule.
    • The crystal structure is effectively stabilized by a characteristic N-H⋯O hydrogen bond, influencing its solid-state packing.