V2EX nucleophilic aromatic substitution

Nucleophilic Aromatic Substitution

释义 Definition

亲核芳香取代(反应):一种有机反应类型,指亲核试剂(nucleophile)进攻芳香环(aromatic ring)上带有离去基团(leaving group)的碳原子,使离去基团被取代。最常见机制是 SNAr 加成消除机制,通常需要芳环上有强吸电子基(如 NO)来稳定中间体(Meisenheimer 复合物)。另有较少见的苯炔(benzyne)机制等。

发音 Pronunciation (IPA)

/nuklflk rmtk sbsttun/

例句 Examples

Nucleophilic aromatic substitution can replace a chlorine atom on an activated benzene ring.
亲核芳香取代可以在被“活化”的苯环上把氯原子替换掉。

In the presence of a strong electron-withdrawing group, nucleophilic aromatic substitution often proceeds via an additionelimination pathway to form the substituted arne.
在强吸电子基团存在时,亲核芳香取代常通过加成消除途径进行,生成取代后的芳香化合物。

词源 Etymology

该术语由三部分组成:nucleophilic(亲核的,源自“nucleus 核”+ “-philic 喜爱的”,表示“喜欢带正电中心/缺电子中心”的试剂)、aromatic(芳香的,指具有芳香性与共轭体系的环,如苯环)、substitution(取代,表示一个基团被另一个基团替换)。合起来即“由亲核试剂参与的芳香环取代反应”。

相关词 Related Words

文献与作品 Literary / Notable Works

  • Organic Chemistry Jonathan Clayden, Nick Greeves, Stuart Warren(有系统介绍 SNAr 与相关影响因素)
  • March’s Advanced Organic Chemistry Michael B. Smith(在取代反应章节讨论亲核芳香取代机理与适用条件)
  • Advanced Organic Chemistry Francis A. Carey & Richard J. Sundberg(常用于高年级/研究生层面的机理讲解)
  • The Art of Writing Reasonable Organic Reaction Mechanisms Robert B. Grossman(以机理推导方式涉及 SNAr 等反应类型)
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