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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.
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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.
1.9K
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
Cholinergic Antagonists: Pharmacokinetics01:24

Cholinergic Antagonists: Pharmacokinetics

1.1K
Cholinergic antagonists—such as antimuscarinics—are available in oral, topical, ocular, parenteral, and inhalational formulations. Most antimuscarinics are oral formulations,  while scopolamine is available as a topical patch, and ipratropium and tiotropium are available as inhalation aerosols or powders. Atropine, tropicamide, and cyclopentolate are topically instilled in the eye. Most antimuscarinics are lipid-soluble and readily absorbed from the gastrointestinal tract and...
1.1K
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
Nondepolarizing (Competitive) Neuromuscular Blockers: Pharmacokinetics01:11

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All neuromuscular blocking agents are injected intravenously because they are poorly absorbed from the GI tract. Rapid onset is achieved with intravenous administration, although absorption is also adequate from an intramuscular injection. Since these agents are highly ionized, they do not readily penetrate cell membranes or cross the blood-brain barrier.
Instead, they are transported by the blood to different tissues. Muscles with a greater blood supply (arteries) and blood flow receive more...
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A Direct, Early Stage Guanidinylation Protocol for the Synthesis of Complex Aminoguanidine-containing Natural Products
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Carbinoxaminium dipicrate.

V Ramya1, Jerry P Jasinski, James P Shannon

  • 1Department of Studies in Chemistry, University of Mysore, Manasagangotri, Mysore 570 006, India.

Acta Crystallographica. Section E, Structure Reports Online
|October 11, 2013
PubMed
Summary

This study details the crystal structure of a carbinoxaminium salt, revealing intermolecular hydrogen bonds and pi-pi interactions. These forces influence the packing and arrangement of the dication and picrate anions in the crystal lattice.

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Area of Science:

  • Crystallography
  • Supramolecular Chemistry
  • Organic Chemistry

Background:

  • Carbinoxamine is an antihistamine with known pharmacological properties.
  • Picrate salts are often used in crystallographic studies due to their properties.

Purpose of the Study:

  • To elucidate the crystal structure of a novel carbinoxaminium picrate salt.
  • To investigate the intermolecular interactions governing crystal packing.

Main Methods:

  • Single-crystal X-ray diffraction analysis was performed.
  • The crystal structure was solved and refined to determine atomic positions and bonding.

Main Results:

  • The structure reveals a carbinoxaminium dication and two picrate anions.
  • Intermolecular N-H⋯O hydrogen bonds and weak C-H⋯O interactions were identified.
  • π-π interactions between picrate anion aromatic rings were observed, with specific centroid-centroid distances noted.

Conclusions:

  • The crystal packing is stabilized by a combination of hydrogen bonding and π-π interactions.
  • The dihedral angles of aromatic rings in the dication and anions provide insights into their spatial arrangement.