V2EX umpolung

Umpolung

释义 Definition

Umpolung(化学/有机化学术语):指“极性反转”,即把某个官能团常见的亲电/亲核性质对调,使其在反应中表现出“反常”的反应性(例如让本来亲电的碳原子变成亲核体参与成键)。

发音 Pronunciation (IPA)

/mpol/

例句 Examples

Umpolung lets us form a new carboncarbon bond in a different way.
极性反转让我们能用不同的方式形成新的碳碳键。

By using a dithiane as an acyl anion equivalent, the synthesis relies on umpolung to reverse the normal polarity of the carbonyl carbon.
通过使用二硫缩醛(dithiane)作为“酰基负离子等价体”,该合成利用极性反转来颠倒羰基碳原子通常的极性与反应性。

词源 Etymology

Umpolung源自德语:**um-**(“反向、倒转”)+ Polung(“极化、极性”)。最初作为德语化学术语使用,后来被英语有机化学界直接借用,用来概括“把常规亲电/亲核角色互换”的策略。

相关词 Related Words

文献作品 Literary Works

  • Advanced Organic Chemistry(Francis A. Carey & Richard J. Sundberg)在讨论“极性反转/合成子(synthon)”策略时常出现该词。
  • March’s Advanced Organic Chemistry(Michael B. Smith;早期版本以 March 为名)在有机反应机理与“等价体”设计章节中提及 umpolung。
  • Dieter Seebach 等关于 dithiane(1,3-二硫杂环戊烷) 作为酰基负离子等价体的经典论文“umpolung”作为核心概念频繁出现。
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