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Diazonium Group Substitution: –OH and –H

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.

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...

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.

Structure of Amines

Structure of Amines

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’ carbon–carbon bond (154 pm). These aspects are illustrated in Figure...

Nomenclature of Secondary and Tertiary Amines

Nomenclature of Secondary and Tertiary Amines

The secondary and tertiary amines are derivatives of ammonia, where two and three of its hydrogens are replaced by alkyl groups, respectively. Secondary and tertiary amines can be symmetrical with identical alkyl groups attached to the nitrogen atom or unsymmetrical when more than one type of alkyl group is present. The standard nomenclature of secondary and tertiary amines is similar to the names given to the primary amines. They are generally named alkylamines. As depicted in Figure 1, for...

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...

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Protocol for the Synthesis of Ortho-trifluoromethoxylated Aniline Derivatives

Protocol for the Synthesis of Ortho-trifluoromethoxylated Aniline Derivatives

Published on: January 19, 2016

4-Nitro-anilinium triiodide monohydrate.

David G Billing¹, Robert S Black, Wonga M Hexana

¹Molecular Sciences Institute, School of Chemistry, University of the Witwatersrand, Private bag, PO Wits 2050, South Africa.

Acta Crystallographica. Section E, Structure Reports Online

|May 18, 2011

Summary

This study reveals how 4-nitro-anilinium cations and water molecules form intricate hydrogen-bonded networks with triiodide anions. These interactions influence crystal packing and molecular geometry in the title compound.

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Area of Science:

Crystal engineering and supramolecular chemistry.
Solid-state chemistry and crystallography.

Background:

Understanding intermolecular interactions is crucial for designing materials with specific properties.
Hydrogen bonding and π-π stacking play significant roles in crystal structure determination.

Purpose of the Study:

To elucidate the crystal structure and hydrogen bonding network of the title compound, 4-nitro-anilinium triiodide monohydrate.
To investigate the influence of these interactions on the molecular conformation and crystal packing.

Main Methods:

Single-crystal X-ray diffraction was employed to determine the three-dimensional structure.
Analysis of hydrogen bonding interactions using graph set notation.
Examination of π-π stacking interactions between aromatic rings.

Main Results:

Triiodide anions form 2D sheets, separated by 4-nitro-anilinium cations and water molecules.
An extended hydrogen-bonded chain involving triiodide, cations, and water was identified (C(3)(3)(14)).
A second hydrogen-bonding interaction (R(2)(2)(6)) between the nitro group, water, and anilinium moiety was observed, affecting the torsion angle and leading to off-center π-π stacking.

Conclusions:

The crystal structure is dominated by two significant hydrogen-bonding networks.
These interactions dictate the arrangement of molecules in the solid state, influencing packing and conformation.
The findings provide insights into the structure-property relationships in nitroaniline derivatives and triiodide salts.