Intermolecular acyl transfer reactivity in several molecular crystals was studied, and the outcome of the reactivity was analyzed in the light of structural information obtained from the crystals of the reactants. Minor changes in the molecular structure resulted in significant variations in the noncovalent interactions and packing of molecules in the crystal lattice, which drastically affected the facility of the intermolecular acyl transfer reactivity in these crystals. Analysis of the reactivity vs crystal structure data revealed dependence of the reactivity on electrophile···nucleophile interactions and C–H···π interactions between the reacting molecules. The presence of these noncovalent interactions augmented the acyl transfer reactivity, while their absence hindered the reactivity of the molecules in the crystal. The validity of these correlations allows the prediction of intermolecular acyl transfer reactivity in crystals and co-crystals of unknown reactivity. This crystal structure–reactivity correlation parallels the molecular structure–reactivity correlation in solution-state reactions, widely accepted as organic functional group transformations, and sets the stage for the development of a similar approach for reactions in the solid state.

中文翻译：

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分子间酰基转移反应性与分子晶体中非共价晶格相互作用的相关性：预测固态有机分子的反应性

研究了几种分子晶体中的分子间酰基转移反应性，并根据从反应物晶体获得的结构信息分析了反应性的结果。分子结构的微小变化导致非共价相互作用和分子在晶格中堆积的显着变化，这极大地影响了这些晶体中分子间酰基转移反应性的便利性。反应性对晶体结构数据的分析表明，反应性依赖于反应分子之间的亲电···亲核相互作用和CH····π相互作用。这些非共价相互作用的存在增强了酰基转移反应性，而它们的缺乏阻碍了晶体中分子的反应性。这些相关性的有效性允许预测未知反应性的晶体和共晶体中的分子间酰基转移反应性。这种晶体结构-反应性相关性与溶液状态反应中的分子结构-反应性相关性平行，被广泛认为是有机官能团转化，并为固态反应类似方法的开发奠定了基础。