Harville Taylor, Gordon Mark S
Department of Chemistry and Ames Laboratory, Iowa State University, Ames, Iowa 50011, USA.
J Chem Phys. 2022 May 7;156(17):174302. doi: 10.1063/5.0090648.
The quasi-atomic orbital (QUAO) bonding analysis is used to study intramolecular hydrogen bonding (IMHB) in salicylic acid and an intermediate that is crucial to the synthesis of aspirin. The bonding analysis rigorously explores IMHB through directly accessing information that is intrinsic to the molecular wave function, thereby bypassing the need for intrinsically biased methods. The variables that affect the strength of IMHB are determined using kinetic bond orders, QUAO populations, and QUAO hybridizations. Important properties include both the interatomic distance between hydrogen and oxygen participating in the IMHB and the hybridization on the oxygen. The bonding analysis further shows that each intramolecular hydrogen bond is a four-electron three-center bond. The bonding analysis is used to understand how aromatic reactivity changes due to the effect of functional groups on the aromatic ring.
准原子轨道（QUAO）键合分析用于研究水杨酸以及阿司匹林合成过程中一种关键中间体的分子内氢键（IMHB）。该键合分析通过直接获取分子波函数固有的信息来严格探究分子内氢键，从而无需使用本质上有偏差的方法。利用动力学键级、QUAO布居和QUAO杂化来确定影响分子内氢键强度的变量。重要性质包括参与分子内氢键的氢和氧之间的原子间距离以及氧上的杂化。键合分析进一步表明，每个分子内氢键都是一个四电子三中心键。键合分析用于理解由于官能团对芳环的影响，芳环反应性是如何变化的。
