硼嗪
化学
芳香性
离域电子
苯
电荷密度
结晶学
等结构
密度泛函理论
计算化学
晶体结构
分子
有机化学
物理
量子力学
氮化硼
作者
María Del Rosario Merino-García,Luis Soriano‐Agueda,Juan de Dios Guzmán-Hernández,Diego Martínez‐Otero,Bruno Landeros‐Rivera,Fernando Cortés‐Guzmán,José Enrique Barquera‐Lozada,Vojtech Jancik
出处
期刊:Inorganic Chemistry
[American Chemical Society]
日期:2022-04-26
卷期号:61 (18): 6785-6798
被引量:11
标识
DOI:10.1021/acs.inorgchem.1c03923
摘要
Although benzene and borazine are isoelectronic and isostructural, they have very different electronic structures, mainly due to the polar nature of the B-N bond. Herein, we present an experimental study of the charge density distribution obtained from the multipole model formalism and Hirshfeld atom refinement (HAR) based on high-resolution X-ray diffraction data of borazine B3N3H6 (1) and B,B',B″-trichloroborazine (2) crystals. These data are compared to those obtained from HAR for benzene (4) and 1,3,5-trichlorobenzene (5) and further compared with values obtained from density functional theory calculations in the gas phase, where N,N',N″-trichloroborazine (3) was also included. The results confirm that, unlike benzene, borazines are only weakly aromatic with an island-like electronic delocalization within the B3N3 ring involving only the nitrogen atoms. Furthermore, delocalization indices and interacting quantum atom energy for bonded and non-bonded atoms were found to be highly suitable indicators capable of describing the origin of the discrepancies observed when the degree of aromaticity in 2 and 3 is evaluated using common aromaticity indices. Additionally, analysis of intermolecular interactions in the crystals brings further evidence of a weakly aromatic character of the borazines as it reveals surprising similarities between the crystal packing of borazine and benzene and also between B,B',B″-trichloroborazine and 1,3,5-trichlorobenzene.
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