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Nucleophilic Substitution Reactions02:34

Nucleophilic Substitution Reactions

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Historical perspective
In 1896, the German chemist Paul Walden discovered that he could interconvert pure enantiomeric (+) and (-) malic acids through a series of reactions. This conversion suggested the involvement of optical inversion during the substitution reaction. Further, in 1930, Sir Christopher Ingold described for the first time two different forms of nucleophilic substitution reactions, which are known as SN1 (nucleophilic substitution unimolecular) and SN2 (nucleophilic substitution...
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Nucleophiles02:30

Nucleophiles

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The word “nucleophile” has a Greek root and translates to nucleus-loving. Nucleophiles are either negatively charged or neutral species with a pair of electrons in a high-energy occupied molecular orbital (HOMO). As these species tend to donate electron pairs, nucleophiles are considered Lewis bases as well. Negatively charged species, like OH−, Cl−, or HS−, with one or several pairs of electrons, are typically nucleophiles. Similarly, neutral species such as...
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Electrophiles02:28

Electrophiles

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This lesson explains the definition, classification, and characteristic features of an electrophile that are key features of nucleophilic substitution reactions. An analysis of their charge and orbital picture helps understand their reactivity for seeking electrons. Electrophiles can be classified into positive and neutral species. Other classes include free radicals and polar functional groups.
While a positive electrophile, like a proton, reacts due to its vacant, low-energy 1s orbital, the...
9.8K
Carboxylic Acids to Acid Chlorides01:18

Carboxylic Acids to Acid Chlorides

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Carboxylic acids react with SOCl2 or PCl5 to form acid chlorides. Amongst the carboxylic acid derivatives, acid chlorides are the most reactive and synthetically important derivatives. They are useful reagents for Friedel–Crafts acylation of some aromatic compounds.
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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

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

2° Amines to N-Nitrosamines: Reaction with NaNO2

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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.
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Supercritical Nitrogen Processing for the Purification of Reactive Porous Materials
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Supercritical Nitrogen Processing for the Purification of Reactive Porous Materials

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プッシュプル仮説の検証:ルイス酸の強化されたN2活性化

Jacob B Geri1, James P Shanahan1, Nathaniel K Szymczak1

  • 1Department of Chemistry, University of Michigan , 930 North University Avenue, Ann Arbor, Michigan 48109, United States.

Journal of the American Chemical Society
|April 18, 2017
PubMed
まとめ

ルイス酸は鉄-二酸化窒素複合体を活性化し,N-N結合の分裂を促進し,陽子化を可能にします. この研究は,様々なルイス酸によるFe ((0) -N2単位 (Fe ((depe) 2 ((N2)) の構造的および電子的変化を調査する.

科学分野:

  • 有機金属化学
  • 無機化学
  • 材料科学

背景:

  • 移行金属複合体による二酸化窒素 (N2) のような小分子活性化は,触媒作用において極めて重要です.
  • N-N結合の活性化を左右する電子的および構造的要因を理解することは,新しい触媒プロセスを開発する上で鍵となる.
  • 鉄が地球に豊富にあるため,鉄-窒素複合体はN2活性化のための有望なプラットフォームを提供します.

研究 の 目的:

  • Fe ((0) -N2ユニットの構造および電子特性に対する外来ルイス酸の影響を体系的に調査する.
  • ルイス酸添加によるN-N結合活性化,酸化還元電位,および偏極化の変化を定量化する.
  • 様々な条件下でN2リガンドでのプロトネーションの実現可能性を調査する.

主な方法:

  • Fe(0-N2複合体の合成と特徴付け (Fe(depe) 2 ((N2)).
  • 中性ボラン,アルカリ金属カチオン,Fe (II) コンプレックスを含む様々なルイス酸の添加.
  • スペクトル解析 (例えば,N-N結合の伸縮周波数シフト,Δ νNNを測定するためのIRスペクトル).
  • 電気化学的研究により,酸化還元電位を決定する.
  • 観測された変化を合理化するための計算研究 (例えば,密度関数理論)

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主要な成果:

  • ルイス酸の添加により,Δ νNNが172cm−1まで上昇すると,N-N結合の活性化は著しく増加する.
  • ルイス酸協調はFe ((0) -N2) リドックスポテンシャルを下げ,鉄中心のより容易な酸化を示します.
  • N-N結合はより極化され,さらなる反応を容易にします.
  • N2リガンドのプロトネーションは異常なアノードポテンシャルで有効にされます.

結論:

  • 外的ルイス酸はFe(0) -N2複合体の電子構造を効果的に調節する.
  • ルイス酸の相互作用は,N-N結合の活性化と極化を促進し,ダイナトロゲンリガンドをプロトネーションのような反応に敏感にします.
  • これらの発見は,鉄複合体によるN2活性化のメカニズムに関する基本的な洞察を提供し,窒素固定のための触媒の設計戦略を提案します.