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Electrophilic Aromatic Substitution: Nitration of Benzene01:20

Electrophilic Aromatic Substitution: Nitration of Benzene

7.4K
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.
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1° Amines to Diazonium or Aryldiazonium Salts: Diazotization with NaNO2 Overview01:26

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

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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...
1.9K
2° Amines to N-Nitrosamines: Reaction with NaNO201:20

2° Amines to N-Nitrosamines: Reaction with NaNO2

3.9K
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.
3.9K
1° Amines to Diazonium or Aryldiazonium Salts: Diazotization with NaNO2 Mechanism01:37

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

3.3K
Nitrous acid is a relatively weak and unstable acid prepared in situ by the reaction of sodium nitrite and cold, dilute hydrochloric acid. In an acidic solution, the nitrous acid undergoes protonation when it loses water to form a nitrosonium ion—an electrophile. Nitrous acid reacts with primary amines to give diazonium salts. The reaction is called diazotization of primary amines.
3.3K
Structure of Amines01:19

Structure of Amines

2.5K
The hybridized nitrogen atom in amines possesses a lone pair of electrons and is bound to three substituents with a bond angle of around 108°, which is less than the tetrahedral angle of 109.5°. However, the C–N–H bond angle is slightly larger at 112°, with a carbon–nitrogen bond length of 147 pm. This carbon–nitrogen bond length of of amines is longer than the carbon–oxygen bond of alcohols (143 pm) but shorter than alkanes’...
2.5K
Preparation of Amines: Alkylation of Ammonia and Amines01:30

Preparation of Amines: Alkylation of Ammonia and Amines

3.9K
Alkylation is one of the methods used to prepare amines. Direct alkylation of ammonia or a primary amine with an alkyl halide gives polyalkylated amines along with a quaternary ammonium salt through successive SN2 reactions. This process of making the quaternary salt through the direct alkylation method is called exhaustive alkylation.
Each alkylation step makes the nitrogen center more nucleophilic, which triggers successive alkylations until a quaternary ammonium salt is formed. Considering...
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Protocol for the Synthesis of Ortho-trifluoromethoxylated Aniline Derivatives
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Protocol for the Synthesis of Ortho-trifluoromethoxylated Aniline Derivatives

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4-Methyl-benzyl-ammonium nitrate.

Sofian Gatfaoui1, Houda Marouani1, Mohamed Rzaigui1

  • 1Laboratoire de Chimie des Matériaux, Faculté des Sciences de Bizerte, 7021 Zarzouna Bizerte, Tunisia.

Acta Crystallographica. Section E, Structure Reports Online
|January 16, 2014
PubMed
Summary

This study details the crystal structure of 4-methyl-benzyl-ammonium nitrate, revealing a layered network formed by hydrogen bonds between cations and anions. The N atom in the cation shows a notable displacement from its plane.

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Area of Science:

  • Crystallography
  • Supramolecular Chemistry
  • Materials Science

Background:

  • Understanding the crystal packing and intermolecular interactions of organic salts is crucial for predicting their physical properties.
  • 4-methyl-benzyl-ammonium nitrate is an organic salt with potential applications in various chemical processes.

Purpose of the Study:

  • To elucidate the crystal structure of 4-methyl-benzyl-ammonium nitrate.
  • To investigate the hydrogen bonding network and other intermolecular interactions within the crystal lattice.

Main Methods:

  • Single-crystal X-ray diffraction was employed to determine the molecular and crystal structure.
  • Analysis of bond lengths, bond angles, and intermolecular distances was performed.

Main Results:

  • The crystal structure of 4-methyl-benzyl-ammonium nitrate (C8H12N(+)·NO3 (-)) was determined.
  • A significant displacement of the nitrogen atom (1.366(2) Å) from the mean plane of the 4-methyl-benzyl-ammonium cation was observed.
  • A layered network structure was identified, stabilized by N-H⋯O and N-H⋯(O,O) hydrogen bonds between cations and anions.
  • A weak C-H⋯O interaction was also detected within the crystal.

Conclusions:

  • The crystal structure of 4-methyl-benzyl-ammonium nitrate is characterized by a non-planar cation and a hydrogen-bonded layered network.
  • The identified hydrogen bonding patterns and weak interactions provide insights into the self-assembly and stability of the crystal structure.