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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.
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.
Nucleophilic Aromatic Substitution: Elimination–Addition01:11

Nucleophilic Aromatic Substitution: Elimination–Addition

Simple aryl halides do not react with nucleophiles. However, nucleophilic aromatic substitutions can be forced under certain conditions, such as high temperatures or strong bases. The mechanism of substitution under such conditions involves the highly unstable and reactive benzyne intermediate. Benzyne contains equivalent carbon centers at both ends of the triple bond, each of which is equally susceptible to nucleophilic attack. This 50–50 distribution of products is confirmed through isotopic...
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...
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...
1° Amines to Diazonium or Aryldiazonium Salts: Diazotization with NaNO2 Overview01:26

1° Amines to Diazonium or Aryldiazonium Salts: Diazotization with NaNO2 Overview

Nitrous acid and nitric acids are two types of acids containing nitrogen, among which nitrous acid is weaker than nitric acid. Nitrous acid with a pKa value of 3.37 ionizes in water to give a nitrite ion and the hydronium ion.
The nitrous acid is unstable. Hence, it is formed in situ from a solution of sodium nitrite and cold aqueous acids such as hydrochloric or sulfuric acid. In an acidic solution, the –OH group of nitrous acid undergoes protonation to give oxonium ion, followed by water loss...

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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

Ethyl 4-butyl-amino-3-nitro-benzoate.

Shivanagere Nagojappa Narendra Babu, Aisyah Saad Abdul Rahim, Shafida Abd Hamid

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

    The crystal structure of ethyl 4-butyl-amino-3-nitro-benzoate reveals three independent molecules. These molecules feature intramolecular hydrogen bonds forming S(6) rings and are further stabilized by intermolecular hydrogen bonds.

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    Area of Science:

    • Crystallography
    • Organic Chemistry
    • Molecular Structure

    Background:

    • The study focuses on the molecular and crystal structure of ethyl 4-butyl-amino-3-nitro-benzoate.
    • Understanding the hydrogen bonding patterns is crucial for predicting material properties.

    Purpose of the Study:

    • To elucidate the crystal structure of ethyl 4-butyl-amino-3-nitro-benzoate.
    • To identify and characterize intra- and intermolecular hydrogen bonding interactions.

    Main Methods:

    • Single-crystal X-ray diffraction was employed to determine the crystal structure.
    • Analysis of the crystal structure involved identifying hydrogen bond donors and acceptors.

    Main Results:

    • The asymmetric unit contains three crystallographically independent ethyl 4-butyl-amino-3-nitro-benzoate molecules.
    • Each molecule exhibits an intramolecular N-H⋯O hydrogen bond, forming a six-membered (S(6)) ring.
    • Intermolecular N-H⋯O and C-H⋯O hydrogen bonds contribute to the overall crystal lattice stabilization.

    Conclusions:

    • The crystal structure provides detailed insights into the molecular arrangement and intermolecular forces.
    • The identified hydrogen bonding network is key to the compound's solid-state architecture.