Exploring influence of fluorine substitution on the strength and nature of halogen bond between iodobenzene and hydrogen cyanide,Journal of Physical Organic Chemistry

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Exploring influence of fluorine substitution on the strength and nature of halogen bond between iodobenzene and hydrogen cyanide
Journal of Physical Organic Chemistry ( IF 1.9 ) Pub Date : 2021-04-15 , DOI: 10.1002/poc.4213
Farhad Fereydooni Naghani ₁ , Saeedreza Emamian ₂ , Karim Zare ₁

Affiliation

In the present study, the intermolecular I … N halogen bond (XB) interaction between iodobenzene (IBZ) and its fluorinated derivatives (as Lewis acids LA 1 through LA 20) with HCN (as Lewis base LB) is theoretically explored to shed light on the electronic nature and strength of the mentioned non-covalent interaction (NCI). The hydrogen atoms of phenyl ring in IBZ were substituted by fluorine atom to probe different impacts of this atom. Such a substitution is paid attention from the number as well as the position of fluorine atoms points of view. Our analyses reveal that this XB interaction whose interaction energy spans a narrow range between 1.0 and 3.0 kcal·mol⁻¹ should be classified as a weak NCI. The symmetry-adapted perturbation theory (SAPT) analysis evidences that the I … N XB in the investigated binary complexes (BCs) is mainly dominated by electrostatic and dispersion interactions, and, in the meantime, induction interactions can safely be ignored. Among the many I … N XB descriptors, V_s,max, which corresponds to the most positive value of electrostatic potential computed for the iodine atom in LAs, plays a key role. Indeed, such an easily and rapidly computable quantity (V_s,max) allows a sufficiently accurate prediction of interaction energy together with SAPT-derived components analysis to become feasible by a simple inclusion of V_s,max value within the numerous explored estimators. Although the strength of I … N XB interaction in the studied BCs is increased by an increase in the number of fluorine substituent, the position of fluorine atom cannot significantly alter the strength of the mentioned interaction.

中文翻译：

探索氟取代对碘苯与氰化氢间卤键强度和性质的影响

在本研究中，理论上探索了碘苯 (IBZ) 及其氟化衍生物（如路易斯酸 LA 1 至 LA 20）与 HCN（作为路易斯碱 LB）之间的分子间 I ... N 卤素键（XB）相互作用，以阐明提到的非共价相互作用 (NCI) 的电子性质和强度。IBZ中苯环的氢原子被氟原子取代以探测该原子的不同影响。从氟原子的数量和位置来看，这种取代受到关注。我们的分析表明，这种 XB 相互作用的相互作用能在 1.0 和 3.0 kcal·mol ^-1之间的狭窄范围内应归类为弱 NCI。对称适应微扰理论 (SAPT) 分析证明，所研究的二元复合物 (BC) 中的 I ... N XB 主要由静电和色散相互作用主导，同时，可以安全地忽略感应相互作用。在许多 I … N XB 描述符中，V _{s , max}对应于为 LA 中碘原子计算的最正静电势值，起着关键作用。事实上，这样一个简单快速的可计算量 ( V _{s , max} ) 允许通过简单地包含V来充分准确地预测相互作用能量以及 SAPT 派生的成分分析变得可行_s，在众多探索的估计量中的_最大值。尽管所研究的 BC 中 I ... N XB 相互作用的强度随着氟取代基数量的增加而增加，但氟原子的位置并不能显着改变上述相互作用的强度。

更新日期：2021-04-15

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