Institute for Molecules and Materials , Radboud University , Heyendaalseweg 135 , 6525 AJ , Nijmegen , The Netherlands.
ICREA , Passeig Lluís Companys 23 , 08010 Barcelona , Spain.
J Org Chem. 2019 Mar 15;84(6):3632-3637. doi: 10.1021/acs.joc.8b03147. Epub 2019 Mar 4.
Although it is well established that the acidity of phenol can be fine-tuned with substituents on its aromatic ring via through-bond effects, the role of through-space effects on the acidity of phenols is presently poorly understood. Here, we present integrated experimental and computational studies on substituted 2,6-diarylphenols that demonstrate the essential contribution from through-space OH-π interactions and O-π interactions in the observed trends in proton affinities and acidities of 2,6-diarylphenols.
虽然通过芳香环上的取代基的键合效应可以很好地调节苯酚的酸度，但目前对于空间效应对苯酚酸度的影响知之甚少。在这里，我们通过对取代的 2,6-二芳基苯酚进行综合的实验和计算研究，证明了空间 OH-π 相互作用和 O-π 相互作用对 2,6-二芳基苯酚质子亲和力和酸度观察到的趋势的重要贡献。
