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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...

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 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.

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...

Ion Exchange

Ion Exchange

Ion exchange chromatography separates charged molecules from a solution by reversibly exchanging them with mobile, or 'active', ions associated with the oppositely charged stationary phase. This method can be used to separate ions, soften and deionize water, and purify solutions. The polymers comprising the ion-exchange column are high-molecular-weight and chemically stable polymers, crosslinked to be porous and essentially insoluble. They are also functionalized with either acidic or basic...

Qualitative Analysis

Qualitative Analysis

For solutions containing mixtures of different cations, the identity of each cation can be determined by qualitative analysis. This technique involves a series of selective precipitations with different chemical reagents, each reaction producing a characteristic precipitate for a specific group of cations. Metal ions within a group are further separated by varying the pH, heating the mixture to redissolve a precipitate, or adding other reagents to form complex ions.
For instance, group IV...

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Updated: Jun 2, 2026

Regioselective O-Glycosylation of Nucleosides via the Temporary 2',3'-Diol Protection by a Boronic Ester for the Synthesis of Disaccharide Nucleosides

Regioselective O-Glycosylation of Nucleosides via the Temporary 2',3'-Diol Protection by a Boronic Ester for the Synthesis of Disaccharide Nucleosides

Published on: July 26, 2018

Decyl-ammonium octa-noate.

Andrew E Jefferson, Chenguang Sun, Andrew D Bond

Acta Crystallographica. Section E, Structure Reports Online

|April 28, 2011

Summary

This summary is machine-generated.

This study reveals a layered crystal structure for a decyl-ammonium compound, stabilized by hydrogen bonds. The alkyl chains exhibit an ortho-rhom-bic packing, deviating from planarity.

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Area of Science:

Crystal Engineering
Supramolecular Chemistry
Materials Science

Background:

Understanding the self-assembly of organic cations and anions is crucial for designing novel materials.
Hydrogen bonding plays a key role in directing the formation of ordered structures.

Purpose of the Study:

To elucidate the crystal structure of the title compound, C(10)H(24)N(+)·C(8)H(15)O(2) (-).
To investigate the role of intermolecular interactions in forming the observed layered architecture.

Main Methods:

Single-crystal X-ray diffraction analysis was employed to determine the three-dimensional crystal structure.
Analysis of hydrogen bonding networks and packing arrangements of the alkyl chains.

Main Results:

The compound forms a layered structure with a two-dimensional network parallel to the (010) plane.
Intermolecular N(+)-H⋯O hydrogen bonds link decyl-ammonium cations and carboxylate anions.
The n-alkyl chains of the decyl-ammonium cations adopt an ortho-rhom-bic subcell packing (approx. 5.1 × 7.3 Å) and show significant distortions from planarity.

Conclusions:

The crystal structure is dictated by a combination of ionic interactions and directional hydrogen bonding.
The packing of the alkyl chains influences the overall structural organization and material properties.