This work provides new insight into assembling and competition between different kinds of interactions for phenol in various solvents. To examine both weak and strong interactions, we selected a series of non-aromatic and aromatic solvents. IR spectra were measured at low (0.05 M) and high (2 M) phenol concentrations. In addition, we calculated (DFT) the structures and harmonic vibrational spectra of 1:1 complexes of phenol with the solvents and the associates of phenol from dimer to tetramer. Based on these results, we divided the solvents into three groups. The first group consists of non-aromatic solvents weakly interacting with phenol. Depending on the concentration, molecules of phenol in these solvents remain non-bonded or self-associated. In diluted solutions of phenol in chlorinated non-aromatic solvents do not appear free OH groups, since they are involved in a weak OH···Cl interaction. The second group consists of aromatic solvents with methyl or chlorine substituents. At low concentrations molecules of phenol are involved in the phenol-solvent OH···π interaction and the strength of these interactions depends on the solvent. At a higher phenol content exists an equilibrium between the phenol-solvent OH···π and phenol-phenol OH···OH interactions. It is of note that in diluted solutions of phenol in tetramethylethylene both the non-bonded and bonded OH coexists. Finally, the third group includes both the aromatic and non-aromatic solvents having highly polar groups like CN. In this case, regardless of the concentration all molecules of phenol are involved in the solute-solvent OH···NC interaction. Comparison of the experimental and theoretical band parameters reveals that molecules of phenol in non-aromatic solvents prefer to create the cyclic associates, while in the aromatic solvents they tend to form the linear associates.

这项工作为苯酚在各种溶剂中的不同相互作用之间的组装和竞争提供了新的见解。为了检查弱相互作用和强相互作用，我们选择了一系列非芳香族和芳香族溶剂。在低 (0.05 M) 和高 (2 M) 苯酚浓度下测量 IR 光谱。此外，我们计算 (DFT) 苯酚与溶剂的 1:1 配合物以及苯酚从二聚体到四聚体的缔合物的结构和谐波振动光谱。基于这些结果，我们将溶剂分为三组。第一组由与苯酚弱相互作用的非芳族溶剂组成。根据浓度，这些溶剂中的苯酚分子保持非键合或自缔合。在氯化非芳香族溶剂中的苯酚稀释溶液中不会出现游离 OH 基团，因为它们参与了弱 OH····Cl 相互作用。第二组由具有甲基或氯取代基的芳族溶剂组成。在低浓度的苯酚分子参与苯酚溶剂 OH····················· 相互作用和这些相互作用的强度取决于溶剂。在较高的苯酚含量下，苯酚溶剂 OH····················································之间存在平衡 和苯酚-苯酚OH····OH 相互作用。值得注意的是，在苯酚在四甲基乙烯中的稀释溶液中，未键合的 OH 和键合的 OH 共存。最后，第三组包括具有高极性基团的芳族和非芳族溶剂，如 C???ºN。在这种情况下，无论浓度如何，所有苯酚分子都参与溶质-溶剂 OH···NC 相互作用。