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

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

1.9K
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
Nomenclature of Secondary and Tertiary Amines01:12

Nomenclature of Secondary and Tertiary Amines

4.2K
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...
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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
Diazonium Group Substitution: –OH and –H01:19

Diazonium Group Substitution: –OH and –H

1.9K
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.
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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

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(Di-methyl-phosphor-yl)methanaminium nitrate.

Claudia M Bianga1, Julia Eggeling1, Guido J Reiss1

  • 1Institut für Anorganische Chemie und Strukturchemie, Lehrstuhl II: Material- und Strukturforschung, Heinrich-Heine-Universität Düsseldorf, Universitätsstrasse 1, D-40225 Düsseldorf, Germany.

Acta Crystallographica. Section E, Structure Reports Online
|January 24, 2014
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Summary

This study reveals dicationic inversion dimers in a crystal structure, linked by hydrogen bonds to form intricate R 2 (2)(10) ring systems. These dimers further assemble into 2D networks with nitrate anions via additional hydrogen bonds.

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Area of Science:

  • Crystal engineering
  • Supramolecular chemistry
  • Hydrogen bonding

Background:

  • Understanding the self-assembly of molecular units is crucial in crystal engineering.
  • Hydrogen bonds play a significant role in directing the formation of extended crystal structures.
  • The specific interactions of dicationic species with counter-anions are key to designing novel materials.

Purpose of the Study:

  • To elucidate the crystal structure of the title salt, C3H11NOP(+)·NO3 (-).
  • To characterize the hydrogen bonding network and supramolecular architecture.
  • To investigate the role of nitrate anions in the crystal packing.

Main Methods:

  • Single-crystal X-ray diffraction analysis was employed to determine the three-dimensional crystal structure.
  • Analysis of hydrogen bonding interactions using geometric criteria.
  • Graph-set descriptor analysis to classify the hydrogen-bonded motifs.

Main Results:

  • The crystal structure features dicationic inversion dimers of C3H11NOP(+) units.
  • These dimers are interconnected via strong N-H⋯O hydrogen bonds, forming R 2 (2)(10) ring systems.
  • Nitrate counter-anions bridge the dicationic dimers through N-H⋯O hydrogen bonds, leading to the formation of 2D networks in the bc plane.

Conclusions:

  • The study successfully characterized a novel crystal structure with a well-defined hydrogen bonding network.
  • The observed R 2 (2)(10) ring system highlights specific self-assembly behavior of the dicationic units.
  • The formation of 2D networks demonstrates the influence of nitrate anions on the overall supramolecular architecture.