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Amination of Aromatic Halides and Exploration of the Reactivity Sequence of Aromatic Halides

Chu Yang1, Feng Zhang2, Guo-Jun Deng1

  • 1The Key Laboratory for Green Organic Synthesis and Application of Hunan Province, The Key Laboratory of Environmentally Friendly Chemistry and Application of the Ministry of Education, College of Chemistry , Xiangtan University , Xiangtan 411105 China.

The Journal of Organic Chemistry
|December 18, 2018
PubMed

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The basicity of aromatic amines is much weaker than that of aliphatic amines due to the involvement of the lone pair of electrons over the N atom in resonance with the aryl rings. Generally, the electron-donating ability of any substituents on the aryl ring of aromatic amines increases the basicity of the amine by increasing electron density, and hence the availability of lone pair on the nitrogen. On the other hand, electron-withdrawing functional groups on the aryl ring of amines decrease the...
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Heterocyclic amines, where the N atom is a part of an alicyclic system, are similar in basicity to alkylamines. Interestingly, the heterocyclic amine having a nitrogen atom as part of an aromatic ring has much less basicity than its corresponding alicyclic counterpart. For this reason, as presented in Figure 1, piperidine (pKb = 2.8) is significantly more basic than pyridine (pKb = 8.8).
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