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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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亚酸 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
概括

研究人员通过光解反应合成了酸 (HPN2), 这项研究描述了HPN2及其光解产物,包括基 (•PN2).

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科学领域:

  • 无机化学
  • 摄影化学
  • 计算化学

背景情况:

  • 酸 (HPN2) 是酸 (HN3) 的重型模拟物.
  • 新型-化合物的合成和表征具有重要意义.
  • 了解这些化合物的光解行为可以揭示新的反应途径和反应中间体.

研究的目的:

  • 合成和描述二酸 (HPN2) 和其同位素.
  • 在不同波长下研究HPN2的光解反应.
  • 探索像基 (•PN2) 这样的新型反应物种的潜在生成.

主要方法:

  • 低温矩阵隔离 (10K) 技术.
  • 使用紫外线辐射的光解反应 (193 nm, 365 nm, 266 nm).
  • 通过矩阵隔离红外 (IR) 和紫外线可见光谱 (UV-vis) 进行表征.
  • 支持量子化学计算 (CCSD) -F12a/cc-pVTZ-F12).

主要成果:

  • 从分子 (N2) 和 (PH3) 或基 (HPCO) 中成功合成基 (HPN2).
  • 使用光谱方法和计算支持对HPN2,DPN2和HP15N2进行表征.
  • 在266 nm的光解导致HPN2中的PN键裂变.
  • 在193nm的光解产生基 (•PN2).

结论:

  • 在特定的低温光解条件下可以合成酸 (HPN2).
  • 光谱和计算数据证实了HPN2及其同位素的结构.
  • HPN2表现出波长依赖的光解,产生不同的产物,包括以前难以捉摸的基 (•PN2).