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芳香环

芳香环是一类有机碳氢芳香化合物,简称芳环[1],概括了纯碳环与杂环两大类。若是成环的原子仅为碳,则特称为芳烃[2]

芳香环拥有共轭的平面环体系,原子间成键并不是不连续的单双键交替,而是被离域π电子云覆盖。典型的芳香环化合物是吲哚

简单芳香环
四元环 含四元环的稠环
 
苯并环丁烯
 
五元环 含五元环的稠环

呋喃

苯并呋喃

异苯并呋喃

吡咯

吲哚

异吲哚

噻吩

苯并[b]噻吩

苯并[c]噻吩

咪唑

苯并咪唑

嘌呤

吡唑

吲唑
 

𫫇唑

苯并𫫇唑
 

异𫫇唑

苯并异𫫇唑
 

噻唑

苯并噻唑
 
六元环 含六元环的稠环




吡啶

喹啉

异喹啉

吡嗪

喹喔啉

吖啶

嘧啶

喹唑啉


哒嗪

噌啉
 

分类

单环

简单的单环芳香化合物一般是五元环(如吡咯)或六元环(如吡啶),

多环与杂环

混合芳香环例如嘌呤是简单环的合并,并共用它们连接的键。当环中有非元素的时候,简单的芳香环就变为了杂环。例如有

含氮的芳香环

含氮的芳香环可以分为非碱性芳香环和碱性芳香环。

  • 非碱性芳香环中,氮原子的孤对电子离域化并参与形成离域π电子云。此类化合物中的氮都与一个原子相连,例如吡咯吲哚
  • 碱性芳香环中,氮原子贡献一个电子参与形成离域π电子云,氮原子的孤对电子则不参与芳香体系,此类含氮碱的碱性即由这个孤对电子所导致,成盐时可以从酸中接受一个氢离子,如同中的氮。此类化合物中的氮不与氢原子形成共价键。例子有:吡啶喹啉
  • 多环化合物中,即便没有碱性氮原子,环也会显示碱性。例如咪唑嘌呤。在酸性条件下,这些化合物质子化形成芳香阳离子(例:吡啶盐)

含氧和硫的芳香环

在有的杂环中,杂环原子中的一对孤对电子参与形成离域π电子云(类似于非碱性含氮杂环),另外一对则延伸至环平面以外(类似于碱性含氮杂环),因此显碱性。

芳香性化合物的特性

  • 分子必须构成环状
  • 每一个原子必须有p轨域,并且每个p轨域必须是完全共轭
  • 要么分子是平面的,要么满足同芳香性莫比乌斯芳香性
  • 分子必须有奇数对π电子,必须满足休克尔规则 (Hückel's rule):(4n+2)个π电子,n为自然数

与之对比的是,有4n个π电子的分子是反芳香性的

参考文献

  1. ^ 存档副本. [2021-04-22]. (原始内容存档于2021-08-23). 
  2. ^ 存档副本. [2021-04-22]. (原始内容存档于2021-04-22). 

参见

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芳香环
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