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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.
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Hybridization of Atomic Orbitals II03:35

Hybridization of Atomic Orbitals II

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sp3d and sp3d 2 Hybridization
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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

3.4K
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...
3.4K
1° Amines to Diazonium or Aryldiazonium Salts: Diazotization with NaNO2 Mechanism01:37

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

4.0K
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
Diazonium Group Substitution with Halogens and Cyanide: Sandmeyer and Schiemann Reactions01:20

Diazonium Group Substitution with Halogens and Cyanide: Sandmeyer and Schiemann Reactions

2.0K
Arenediazonium substitution reactions occur when the diazonium group is substituted by various functional groups such as halides, hydroxyl, nitrile, etc. For instance, arenediazonium salts react with copper(I) salts of chloride, bromide, or cyanide to form corresponding aryl chlorides, bromides, and nitriles. These reactions are named Sandmeyer reactions. Although the mechanism of this reaction is complicated, as illustrated in Figure 1, they are believed to progress via an aryl copper...
2.0K
Nucleophilic Aromatic Substitution of Aryldiazonium Salts: Aromatic SN101:14

Nucleophilic Aromatic Substitution of Aryldiazonium Salts: Aromatic SN1

2.2K
Treating arylamines with nitrous acid gives aryldiazonium salts that are effective substrates in nucleophilic aromatic substitution reactions. The diazonio group in these salts can be easily displaced by different nucleophiles, yielding a wide variety of substituted benzenes. The leaving group departs as nitrogen gas, and this easy elimination is the driving force for the substitution reaction.
In the Sandmeyer reaction, for example, the diazonio group is replaced by a chloro, bromo,...
2.2K

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Preparation and Reactivity of a Triphosphenium Bromide Salt: A Convenient and Stable Source of PhosphorusI
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Diazophosphane HPN2.

Bo Lu1, Xin Shao1, Xin Jiang1

  • 1Department of Chemistry, Shanghai Key Laboratory of Molecular Catalysts and Innovative Materials, Fudan University, Shanghai 200433, China.

Journal of the American Chemical Society
|November 29, 2022
PubMed
Summary

Researchers synthesized diazophosphane (HPN2), a heavy analog of hydrazoic acid, using photolytic reactions. This study characterizes HPN2 and its photolysis products, including the phosphinyl radical (•PN2).

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Area of Science:

  • Inorganic Chemistry
  • Photochemistry
  • Computational Chemistry

Background:

  • Diazophosphane (HPN2) is a heavy analog of hydrazoic acid (HN3).
  • The synthesis and characterization of novel phosphorus-nitrogen compounds are of significant interest.
  • Understanding the photolytic behavior of such compounds can reveal new reaction pathways and reactive intermediates.

Purpose of the Study:

  • To synthesize and characterize diazophosphane (HPN2) and its isotopologues.
  • To investigate the photolytic reactions of HPN2 at different wavelengths.
  • To explore the potential generation of novel reactive species like the phosphinyl radical (•PN2).

Main Methods:

  • Low-temperature matrix-isolation (10 K) techniques.
  • Photolytic reactions using UV irradiation (193 nm, 365 nm, 266 nm).
  • Characterization via matrix-isolation infrared (IR) and UV-visible (UV-vis) spectroscopy.
  • Supportive quantum chemical calculations (CCSD(T)-F12a/cc-pVTZ-F12).

Main Results:

  • Successful synthesis of diazophosphane (HPN2) from molecular nitrogen (N2) and phosphine (PH3) or phosphaketene (HPCO).
  • Characterization of HPN2, DPN2, and HP15N2 using spectroscopic methods and computational support.
  • Photolysis at 266 nm leads to P-N bond cleavage in HPN2.
  • Photolysis at 193 nm generates the phosphinyl radical (•PN2).

Conclusions:

  • Diazophosphane (HPN2) can be synthesized under specific low-temperature photolytic conditions.
  • The spectroscopic and computational data confirm the structure of HPN2 and its isotopologues.
  • HPN2 exhibits wavelength-dependent photolysis, yielding different products including the previously elusive phosphinyl radical (•PN2).