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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...
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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

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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.
4.0K
Alkyl Halides02:45

Alkyl Halides

17.1K
Structural Properties
Alkyl halides are halogen-substituted alkanes wherein one or more hydrogen atoms of an alkane is replaced by a halogen atom such as fluorine, chlorine, bromine, or iodine. The carbon atom in an alkyl halide is bonded to the halogen atom, which is sp3-hybridized and exhibits a tetrahedral shape.
Unlike alkyl halides, compounds in which a halogen atom is bonded to an sp2 -hybridized carbon atom of a carbon-carbon double bond (C=C) are called vinyl halides. Whereas aryl...
17.1K
Diazonium Group Substitution: –OH and –H01:19

Diazonium Group Substitution: –OH and –H

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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.
2.9K
Acid Halides to Amides: Aminolysis01:07

Acid Halides to Amides: Aminolysis

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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...
3.0K
Aldehydes and Ketones with Amines: Imine Formation Mechanism01:23

Aldehydes and Ketones with Amines: Imine Formation Mechanism

6.2K
Imine formation involves the addition of carbonyl compounds to a primary amine. It begins with the generation of carbinolamine through a series of steps involving an initial nucleophilic attack and then several proton transfer reactions. The second part includes the elimination of water, as a leaving group, to give the imine.
Imines are formed under mildly acidic conditions. A pH of 4.5 is ideal for the reaction.
If the pH is low or the solution is too acidic, the reaction slows down in the...
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1-Methyl-5-nitro-imidazolium chloride.

Sophia Bellia1, Grace Anderson2, Matthias Zeller3

  • 1Ave Maria University, Department of Chemistry and Physics, 5050 Ave Maria Blvd, Ave Maria, Florida 34142, USA.

Iucrdata
|November 7, 2022
PubMed
Summary

This study details the hydrogen bonding interactions in a nitro-imidazolium chloride salt. Key findings include strong H⋯Cl bonds and anion-π interactions, revealing the crystal structure.

Keywords:
crystal structurehydrogen bondingimidazoliumπ-hole

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Area of Science:

  • Crystallography
  • Supramolecular Chemistry
  • Materials Science

Background:

  • Understanding intermolecular forces is crucial for designing novel materials.
  • Nitro-imidazolium salts are of interest due to their potential applications.

Purpose of the Study:

  • To investigate the hydrogen bonding network and crystal structure of a specific nitro-imidazolium chloride salt.
  • To characterize the nature and strength of various intermolecular interactions present.

Main Methods:

  • Single-crystal X-ray diffraction was employed to determine the crystal structure.
  • Analysis of hydrogen bonding and other non-covalent interactions was performed.

Main Results:

  • The crystal structure reveals extensive hydrogen bonding between the nitro-imidazolium cation and chloride anion.
  • Specific H⋯Cl interactions were identified, with the central aromatic hydrogen showing a shorter interaction.
  • Anion-π interactions were observed, while typical π-π stacking was absent. The crystal was refined as a two-component twin.

Conclusions:

  • The study elucidates the intricate intermolecular interactions governing the solid-state structure of this ionic compound.
  • The findings contribute to the understanding of crystal engineering principles for related ionic materials.