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Preparation and Reactions of Thiols02:33

Preparation and Reactions of Thiols

7.3K
Thiols are prepared using the hydrosulfide anion as a nucleophile in a nucleophilic substitution reaction with alkyl halides. For instance, bromobutane reacts with sodium hydrosulfide to give butanethiol.
7.3K
Radical Substitution: Hydrogenolysis of Alkyl Halides with Tributyltin Hydride01:26

Radical Substitution: Hydrogenolysis of Alkyl Halides with Tributyltin Hydride

2.2K
Radical substitution reactions can be used to remove functional groups from molecules. The hydrogenolysis of alkyl halides is one such reaction, where the weak Sn–H bond in tributyltin hydride reacts with alkyl halides to form alkanes. Here, the reagent Bu3SnH yields tributyltin halide as a byproduct.
The bonds formed in this reaction are stronger than the bonds broken, making it energetically favorable. The reaction follows a radical chain mechanism similar to radical halogenation reactions,...
2.2K
Nitriles to Amines: LiAlH4 Reduction00:55

Nitriles to Amines: LiAlH4 Reduction

4.5K
Nitriles are reduced to amines in the presence of strong reducing agents like lithium aluminum hydride through a typical nucleophilic acyl substitution. The reaction requires two equivalents of the reducing agent. The reducing agent acts as a source of hydride ions.
As shown below, the mechanism involves three steps. Firstly, the hydride ion acting as a nucleophile attacks the nitrile carbon to form an anion. In the second step, a second equivalent of the hydride ion attacks the anion to...
4.5K
1° Amines to Diazonium or Aryldiazonium Salts: Diazotization with NaNO2 Overview01:26

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

3.8K
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...
3.8K
Aldehydes and Ketones with HCN: Cyanohydrin Formation Mechanism01:10

Aldehydes and Ketones with HCN: Cyanohydrin Formation Mechanism

4.1K
Cyanohydrins are formed when cyanide nucleophiles and carbonyl compounds like aldehydes and ketones react. A strong base, the cyanide ion, catalyzes cyanohydrin formation. The ions are generated from HCN under aqueous conditions. Once the cyanide ions are generated, the first step involves the nucleophilic attack of the cyanide ions on the electrophilic carbonyl carbon. This attack shifts the π electrons from the C=O to the oxygen atom forming the alkoxide ion intermediate. The alkoxide anion...
4.1K
Acid Halides to Alcohols: LiAlH4 Reduction01:19

Acid Halides to Alcohols: LiAlH4 Reduction

3.7K
Acid halides are reduced to alcohols in the presence of a strong reducing agent like lithium aluminum hydride.
The mechanism proceeds in three steps. First, the nucleophilic hydride ion attacks the carbonyl carbon of the acid halide to form a tetrahedral intermediate. Next, the carbonyl group is re-formed, and the halide ion departs as a leaving group, generating an aldehyde. A second nucleophilic attack by the hydride yields an alkoxide ion, which, upon protonation, gives a primary alcohol as...
3.7K

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関連する実験動画

Updated: Dec 25, 2025

Protein Film Infrared Electrochemistry Demonstrated for Study of H2 Oxidation by a [NiFe] Hydrogenase
10:01

Protein Film Infrared Electrochemistry Demonstrated for Study of H2 Oxidation by a [NiFe] Hydrogenase

Published on: December 4, 2017

12.6K

H2 チオラート結合ニオールヒドリドからの進化

Nina X Gu1, Paul H Oyala1, Jonas C Peters1

  • 1Division of Chemistry and Chemical Engineering, California Institute of Technology, Pasadena, California 91125, United States.

Journal of the American Chemical Society
|April 7, 2020
PubMed
まとめ
この要約は機械生成です。

研究者が合成した ターミナルニッケルヒドリド複合体は 陽子還元における重要な中間物質です このパラマグネティックなニッケル・チオラート・ヒドリドの種は,水素を放出し,触媒への洞察を提供することを特徴付けました.

さらに関連する動画

Synthesis of a Thiol Building Block for the Crystallization of a Semiconducting Gyroidal Metal-sulfur Framework
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Synthesis of a Thiol Building Block for the Crystallization of a Semiconducting Gyroidal Metal-sulfur Framework

Published on: April 9, 2018

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The Synthesis, Characterization and Reactivity of a Series of Ruthenium N-triphosPh Complexes
10:51

The Synthesis, Characterization and Reactivity of a Series of Ruthenium N-triphosPh Complexes

Published on: April 10, 2015

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関連する実験動画

Last Updated: Dec 25, 2025

Protein Film Infrared Electrochemistry Demonstrated for Study of H2 Oxidation by a [NiFe] Hydrogenase
10:01

Protein Film Infrared Electrochemistry Demonstrated for Study of H2 Oxidation by a [NiFe] Hydrogenase

Published on: December 4, 2017

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Synthesis of a Thiol Building Block for the Crystallization of a Semiconducting Gyroidal Metal-sulfur Framework
12:30

Synthesis of a Thiol Building Block for the Crystallization of a Semiconducting Gyroidal Metal-sulfur Framework

Published on: April 9, 2018

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The Synthesis, Characterization and Reactivity of a Series of Ruthenium N-triphosPh Complexes
10:51

The Synthesis, Characterization and Reactivity of a Series of Ruthenium N-triphosPh Complexes

Published on: April 10, 2015

12.6K

科学分野:

  • 無機化学
  • カタリシス
  • バイオ有機化学

背景:

  • ターミナルニッケル水素は,分子電気触媒と金属酵素によって触媒化された陽子還元反応における重要な中間物質である.
  • 準磁性ニッケル水化物複合体の明確な例は稀であり,特に端末水化物を含むものは稀であり,最も知られている例はブリッジング水化物を含む.

研究 の 目的:

  • S=1/2で,はっきりと定義された末端結合のチオラート-ニオール-III-H複合体を合成し,特徴づける.
  • 最先端のヒドリドリガンドの電子構造と性質を,先端のスペクトロスコープと計算方法を用いて調査する.
  • 合成された複合体の反応性,特に水素 (H2) 進化への傾向を探求する.

主な方法:

  • 新しいチオラート-ニオール-III-H複合体の合成
  • パルス EPR 試験を含む振動スペクトロスコーピーと電子パラマグネティック共振 (EPR) を用いた特徴付け.
  • 電子構造とスピン分布を分析するための密度関数理論 (DFT) の計算.
  • H2の二分子還元性除去をモニターする運動研究

主要な成果:

  • S = 1/2の末端結合のチオラート-ニオール-III-H複合体の合成に成功した.
  • 徹底した特徴付けにより,末端ヒドリドリガンドの存在と性質が確認され,EPR研究により,チオラートリガンドへのスピン漏れが示された.
  • DFTの計算は電子構造に関する実験的発見を裏付けました.
  • 複合体は加熱時にH2の二分子還元性排出を観察し,動力学的研究はこの反応に関するデータを提供した.

結論:

  • この研究は,パラマグネティックで末端に結合したチオラート-ニオール-III-H複合体の最初のよく定義された例を報告している.
  • 特徴づけられた複合体は,触媒性陽子還元における提案されたニッケル水素中介物の貴重なモデルとして機能する.
  • 双分子還元性除去による観察されたH2の進化は,ヒドロゲネーゼ酵素と合成触媒に関連するメカニズム的洞察を提供します.