Hydrolysis of acetanilides and aminolysis of phenyl and thiophenyl acetates are related reactions since these are processes of nucleophilic substitution on the carbonyl carbon. Current views of chemical reactivity based on the DFT theory rely upon reactivity indices that are descriptors of both the reaction center and the molecule as a whole, and have not been applied to the given processes before. One of such descriptors is an atomic electrostatic potential. The given parameter was calculated by the DFT theory M06/6-311+G (non-specific solvation, MeCN, SMD, and full optimization) for the structures of substituted phenyl acetates XPhO-C(O)Me, acetanilides XPhNHC(O)Me, thiophenyl acetates ZPhSC(=O)Me, and benzyl amines XPhСH2NH2 (X, Z substituents). It has been found that all relationships between the atomic electrostatic potential, the charge on the reaction center in the Hirshfeld scheme, and logK are symbatic. Consequently, in all of the cases, the rate is determined by the nucleophilic attack on the reaction center, with the activity/selectivity relationship being observed. The fact that the reaction rate is limited by the nucleophilic attack of the reagent is not inconsistent with the views of the reaction being concerted, since it is known that such reactions may be quite concerted though not quite synchronous.

中文翻译：

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原子静电势作为乙酸苯酯和苯硫苯酯的氨解以及乙酰苯胺的水解的描述

乙酰苯胺的水解和乙酸苯酯和苯硫基苯酯的氨解是相关反应，因为这些是羰基碳上的亲核取代过程。当前基于 DFT 理论的化学反应性观点依赖于反应性指数，反应性指数是反应中心和整个分子的描述符，并且之前尚未应用于给定的过程。这些描述符之一是原子静电势。给定的参数是通过 DFT 理论 M06/6-311+G（非特异性溶剂化、MeCN、SMD 和完全优化）计算的，用于取代乙酸苯酯 XPhO-C(O)Me、乙酰苯胺 XPhNHC(O) 的结构Me、乙酸噻吩酯 ZPhSC(=O)Me 和苄胺 XPhСH2NH2（X、Z 取代基）。已经发现原子静电势、赫什菲尔德方案中反应中心的电荷和logK之间的所有关系都是对称的。因此，在所有情况下，速率由对反应中心的亲核攻击决定，并观察活性/选择性关系。反应速率受到试剂的亲核攻击的限制这一事实与协调反应的观点并不矛盾，因为已知这种反应尽管不完全同步但可能是相当协调的。