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Nucleophilic aromatic substitution reactions play a crucial role in the synthesis of organic compounds and are considered to be one of the most important synthetic transformations. Traditionally, these reactions have been described as stepwise processes in textbooks. However, with further research, the existence of concerted nucleophilic aromatic substitution reactions has been widely confirmed. This paper provides a brief overview of the stepwise pathway of nucleophilic aromatic substitution reactions and focuses on several examples of concerted reactions, highlighting the importance of reaction design in mechanistic studies. Integrating cutting-edge research findings into teaching can enhance students’ understanding of nucleophilic aromatic substitution reactions. [ABSTRACT FROM AUTHOR]

The structures and energies of various common carbocations, allylic carbocations, and particularly stable α-amino and α-hydroxyl carbocations were calculated using DFT (density functional theory). The results showed that common carbocations are stabilized by the formation of supercovalent structures, rearrangement, and superconjugation effects, whereas allylic carbocations are stabilized by conjugate effects. The stabilities of α-hydroxyl and α-amino carbocations are particularly high and are equivalent to or higher than that of cyclopropylene carbocation. Finally, different methods of carbocation stabilization using amino and hydroxyl groups are suggested. [ABSTRACT FROM AUTHOR]

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