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

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...

2° Amines to N-Nitrosamines: Reaction with NaNO2

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.

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

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

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.

Preparation of Acid Anhydrides

Preparation of Acid Anhydrides

One of the methods for preparing symmetrical or unsymmetrical acid anhydrides involves the treatment of acid chlorides with the sodium salt of carboxylic acids. The reaction proceeds via a nucleophilic acyl substitution.
The carboxylate ion acts as a nucleophile that attacks the carbonyl carbon of the acid chloride to form a tetrahedral intermediate. Subsequently, the re-formation of the carbonyl group with the loss of the chloride ion as a leaving group leads to the formation of an acid...

Preparation of Nitriles

Preparation of Nitriles

One of the common methods to prepare nitriles is the dehydration of amides. This method requires strong dehydrating agents like phosphorous pentoxide or boiling acetic anhydride for converting amides to nitriles. Another reagent namely, thionyl chloride also accomplishes the dehydration of amides, where amide acts as a nucleophile. The first step of the mechanism involves the nucleophilic attack by the amide on the thionyl chloride to form an intermediate. In the next step, the electron pairs...

Acid Halides to Amides: Aminolysis

Acid Halides to Amides: Aminolysis

Aminolysis is a nucleophilic acyl substitution reaction, where ammonia or amines act as nucleophiles to give the substitution product. Acid halides react with ammonia, primary amines, and secondary amines to yield primary, secondary, and tertiary amides, respectively.
In the first step of the aminolysis mechanism, the amine attacks the carbonyl carbon of the acyl chloride to form a tetrahedral intermediate. In the second step, the carbonyl group is re-formed with the elimination of a chloride...

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5-Chloro-2-methoxy-anilinium nitrate.

Hanene Hemissi¹, Sonia Abid, Mohamed Rzaigui

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

Acta Crystallographica. Section E, Structure Reports Online

|January 5, 2011

Summary

This study details the crystal structure of a title salt, highlighting extensive hydrogen bonding and pi-pi interactions that form corrugated layers. These interactions are key to understanding the compound's solid-state structure.

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Area of Science:

Crystallography
Supramolecular Chemistry
Materials Science

Background:

Understanding the intermolecular forces governing crystal packing is crucial for predicting and controlling material properties.
Hydrogen bonding and pi-pi interactions are fundamental non-covalent interactions that significantly influence molecular assembly in the solid state.

Purpose of the Study:

To elucidate the crystal structure of the title salt, C(7)H(9)ClNO(+)·NO(3)(-).
To investigate the role of hydrogen bonding and pi-pi interactions in the self-assembly of the title salt.
To characterize the resulting two-dimensional network and molecular orientation.

Main Methods:

Single-crystal X-ray diffraction was employed to determine the molecular and crystal structure.
Analysis of intermolecular distances and angles was performed to identify and quantify hydrogen bonding and pi-pi interactions.

Main Results:

The title salt crystallizes with extensive hydrogen bonding between the ammonium group and the nitrate anion.
A two-dimensional network of bifurcated N-H⋯O hydrogen bonds was observed, forming corrugated layers in the bc plane.
Organic molecules are arranged in a parallel orientation due to pi-pi interactions, with an inter-ring distance of 3.837 Å.

Conclusions:

The crystal structure is dominated by a combination of strong hydrogen bonding and pi-pi stacking interactions.
These interactions lead to the formation of a unique corrugated layered structure.
The findings provide insights into the structure-property relationships of organic salts with potential applications in materials science.