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関連する概念動画

1° Amines to Diazonium or Aryldiazonium Salts: Diazotization with NaNO2 Overview01:26

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

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 water loss...
2° Amines to N-Nitrosamines: Reaction with NaNO201:20

2° Amines to N-Nitrosamines: Reaction with NaNO2

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.
Preparation of Amines: Reduction of Oximes and Nitro Compounds01:29

Preparation of Amines: Reduction of Oximes and Nitro Compounds

Oximes can be reduced to primary amines using catalytic hydrogenation, hydride reduction, or sodium metal reduction. The reduction of aliphatic and aromatic nitro compounds to primary amines takes place by either catalytic hydrogenation or by using active metals like Fe, Zn, and Sn in the presence of an acid.
Though catalytic hydrogenation can reduce nitrobenzenes, the reduction is nonselective in the presence of other functional groups. For instance, if nitrobenzene contains an aldehyde group,...
1° Amines to Diazonium or Aryldiazonium Salts: Diazotization with NaNO2 Mechanism01:37

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

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.
Nitrosation of Enols01:19

Nitrosation of Enols

The nitrosation reaction is one of the methods of preparing 1,2-diketones. The enol tautomer of the starting ketone reacts with sodium nitrite in hydrochloric acid, generating the 1,2-diketone after hydrolysis.
Diazonium Group Substitution: –OH and –H01:19

Diazonium Group Substitution: –OH and –H

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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関連する実験動画

Updated: Jun 7, 2026

A Direct, Regioselective and Atom-Economical Synthesis of 3-Aroyl-N-hydroxy-5-nitroindoles by Cycloaddition of 4-Nitronitrosobenzene with Alkynones
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ニトロキシドで置換されたニトロニルニトロキシドとイミノニトロキシド

Shuichi Suzuki1, Takanori Furui, Masato Kuratsu

  • 1Department of Chemistry, Graduate School of Science, Osaka City University, Sugimoto Sumiyoshi-ku, Osaka 558-8585, Japan.

Journal of the American Chemical Society
|October 23, 2010
PubMed
まとめ

2つの新しいダイラジカル,ニトロニル窒酸化物1とイミノニトロ酸化物2は,安定した,コンパクトな構造を示し,有意な陽性磁気交換相互作用があり,高度な磁気材料の可能性を秘めています.

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Chemiluminescence-based Assays for Detection of Nitric Oxide and its Derivatives from Autoxidation and Nitrosated Compounds
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Chemiluminescence-based Assays for Detection of Nitric Oxide and its Derivatives from Autoxidation and Nitrosated Compounds

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Syntheses, Crystallization, and Spectroscopic Characterization of 3,5-Lutidine N-Oxide Dehydrate
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Syntheses, Crystallization, and Spectroscopic Characterization of 3,5-Lutidine N-Oxide Dehydrate

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関連する実験動画

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A Direct, Regioselective and Atom-Economical Synthesis of 3-Aroyl-N-hydroxy-5-nitroindoles by Cycloaddition of 4-Nitronitrosobenzene with Alkynones
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Chemiluminescence-based Assays for Detection of Nitric Oxide and its Derivatives from Autoxidation and Nitrosated Compounds
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Chemiluminescence-based Assays for Detection of Nitric Oxide and its Derivatives from Autoxidation and Nitrosated Compounds

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Syntheses, Crystallization, and Spectroscopic Characterization of 3,5-Lutidine N-Oxide Dehydrate
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Syntheses, Crystallization, and Spectroscopic Characterization of 3,5-Lutidine N-Oxide Dehydrate

Published on: April 24, 2018

科学分野:

  • オーガニック化学 オーガニック化学
  • マテリアルサイエンス 材料科学
  • マグネティズム (磁気) とは

背景:

  • ダイラジカルとは,2つのペアリングされていない電子を持つ分子であり,磁気現象を理解するために重要である.
  • 窒素酸化物で置換されたニトロニル窒素酸化物とイミノニトロキシドは,ユニークな電子特性を持つ有機根子のクラスを表しています.

研究 の 目的:

  • 新しく,非常にコンパクトなディラジカルを合成し,特徴づけること.
  • これらの新しいダイラジカル系における磁気交換相互作用を調査する.

主な方法:

  • ニトロニルニトロキシド1とイミノニトロキシド2の合成
  • ダイラジカルの構造と電子的特徴.
  • 交換相互作用を決定するための磁気感受性測定.

主要な成果:

  • 非常にコンパクトな窒素酸化物を代用したニトロニル窒素酸化物1とイミノニトロ酸化物2の合成に成功しました.
  • 両方のダイラディカルは,周囲の空気条件下での安定性を示した.
  • 大きな正の磁気交換相互作用が定量化されました: J/k(B) = +390 K for 1とJ/k(B) ≈ +550 K for 2.

結論:

  • 合成されたダイラジカルは,トリメチレンメタンに類似したアイソ電子構造を持っています.
  • その安定性と,重要なポジティブな交換相互作用により,分子磁気と先進的な材料の有望な候補となる.