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Diazonium Group Substitution: –OH and –H01:19

Diazonium Group Substitution: –OH and –H

2.9K
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.
2.9K
Hybridization of Atomic Orbitals II03:35

Hybridization of Atomic Orbitals II

32.8K
sp3d and sp3d 2 Hybridization
32.8K
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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Preparation and Reactivity of a Triphosphenium Bromide Salt: A Convenient and Stable Source of PhosphorusI

Published on: November 22, 2016

7.8K

ディアゾフォスファン 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
まとめ

研究者は光分解反応を用いて,ヒドラゾ酸の重量類であるダイアゾフォスファン (HPN2) を合成した. この研究では,フォスフィニル基 (•PN2) を含むHPN2とその光分解産物について特徴づけています.

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Last Updated: Aug 19, 2025

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Preparation and Use of Carbonyl-decorated Carbenes in the Activation of White Phosphorus
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科学分野:

  • 無機化学
  • 写真化学
  • コンピュータ化学

背景:

  • ディアゾフォスファン (HPN2) は,ヒドラゾ酸 (HN3) の重量類である.
  • 新しいリン酸化窒素化合物の合成と特徴付けは,重要な関心事である.
  • このような化合物の光分解的振る舞いを理解すると,新しい反応経路と反応性中間物質が明らかになる.

研究 の 目的:

  • ディアゾフォスファン (HPN2) とその同位体の合成と特徴づけ
  • 異なる波長でのHPN2の光分解反応を調査する.
  • フォスフィニルラジカル (•PN2) のような新種の反応性の生成の可能性を調査する.

主な方法:

  • 低温マトリックス隔離 (10K) 技術
  • 紫外線照射を用いた光分解反応 (193 nm, 365 nm, 266 nm)
  • マトリックス隔離型赤外線 (IR) と可視紫外線 (UV-vis) のスペクトロスコーピーによる特徴付け.
  • 補助的な量子化学計算 (CCSD(T) -F12a/cc-pVTZ-F12).

主要な成果:

  • 分子窒素 (N2) とホスフィン (PH3) またはホスファケテン (HPCO) からダイアゾフォスファン (HPN2) の合成に成功した.
  • HPN2,DPN2,およびHP15N2の特徴は,スペクトロスコピ的方法と計算的サポートを用いて作成した.
  • 266 nmでの光分解は,HPN2におけるPN結合の割れにつながります.
  • 193 nmでの光分解により,フォスフィニル基 (•PN2) が生成される.

結論:

  • ディアゾフォスファン (HPN2) は,特定の低温光分解条件下で合成することができる.
  • 分光学および計算データにより,HPN2とその同位体の構造が確認されました.
  • HPN2は波長に依存する光分解を行い,以前は捉え難いフォスフィニル基 (•PN2) を含むさまざまな製品を生成します.