DFT-derived reactivity descriptors and Non-Covalent interaction (NCI) analysis were performed to rationalize the regioselectivity in the amination reaction of some isoquinolinequinone derivatives. Statistical analysis was performed to assess robustness of atomic charges to the basis set. Various electronic population schemes including Mulliken population analysis (MPA), electrostatic method (ChelpG), Hirshfeld population analysis (HPA) and Natural population analysis (NPA) have been considered. The results revealed that NPA was the most efficient for this purpose. NCI study using the reduced density gradient (RDG) was performed for revealing weak interactions. Domains defined by isosurfaces of RDG have been integrated to quantitatively study the strength of weak interactions and their stabilities have also been examined. Steric hindrance caused by coordination of ethanol with the neighboring carbonyl prevents the nucleophilic attack on C-6 and therefore leads to preferential C-7 substitution. The quantitative study of NCI clearly demonstrates that the hydrogen bond of carbonyl (2) is more stabilizing. Consequently, the high polarity of hydrogen bond on this carbonyl may explain the high electrophilicity of C-5 compared to C-8. Our work proved that the difference in local reactivity, as well as the steric hindrance are the key elements explaining the high regioselectivity exhibited by the amination reaction.

进行了DFT衍生的反应性描述符和非共价相互作用（NCI）分析，以合理化某些异喹啉醌衍生物的胺化反应中的区域选择性。进行统计分析以评估原子电荷对基集的稳健性。已经考虑了各种电子人口计划，包括Mulliken人口分析（MPA），静电法（ChelpG），Hirshfeld人口分析（HPA）和自然人口分析（NPA）。结果表明，NPA是最有效的方法。使用降低的密度梯度（RDG）进行了NCI研究，以揭示弱相互作用。由RDG的等值面定义的域已被集成以定量研究弱相互作用的强度，并且还检查了它们的稳定性。乙醇与相邻羰基的配位引起的立体位阻可防止对C-6的亲核攻击，因此可导致优先进行C-7取代。NCI的定量研究清楚地表明，羰基（2）的氢键更稳定。因此，与C-8相比，该羰基上氢键的高极性可以解释C-5的高亲电性。我们的工作证明，局部反应性的差异以及位阻是解释胺化反应所显示的高区域选择性的关键因素。因此，与C-8相比，该羰基上氢键的高极性可以解释C-5的高亲电性。我们的工作证明，局部反应性的差异以及位阻是解释胺化反应所显示的高区域选择性的关键因素。因此，与C-8相比，该羰基上氢键的高极性可以解释C-5的高亲电性。我们的工作证明，局部反应性的差异以及位阻是解释胺化反应所显示的高区域选择性的关键因素。