A study of the global and local aromaticity of hetero[8]circulenes

IF 1.9 4区 化学 Q2 CHEMISTRY, ORGANIC Journal of Physical Organic Chemistry Pub Date : 2024-04-11 DOI:10.1002/poc.4609
Satewaerdi Helili, Ablikim Kerim
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Abstract

The topological resonance energy (TRE) method was used to investigate the aromaticity of hetero[8]circulenes in both their neutral and doubly charged ion states. The compounds varying stabilities in different charged states were explained in terms of the topological charge stabilization rule. The TRE-based aromaticity indices were compared with those obtained by the gauge-including magnetically induced currents (GIMIC) method. However, the lack of correlation between the TRE and GIMIC aromaticity indices, as well as the contradictory trends observed, suggest that further investigation is necessary to fully understand the aromaticity of hetero[8]circulenes. We employed the circuit resonance energy (CRE) method to assess local aromaticity. Our CRE results indicate that individual benzene or heterocyclic five-membered units within the molecule maintain their strong aromatic character and serve as the primary source of global aromaticity, both in their neutral and doubly charged ion states. Although our CRE results provide valuable insights, it is important to note that there are cases where the magnitude of local aromaticity predicted by the nucleus-independent chemical shift (NICS[0] and NICS[1]) indices does not align with our CRE results.

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杂[8]环烯的整体和局部芳香性研究
拓扑共振能(TRE)方法用于研究杂[8]环烯在中性和双电荷离子状态下的芳香性。根据拓扑电荷稳定规则解释了化合物在不同带电状态下的不同稳定性。将基于 TRE 的芳香指数与通过量规包括磁感应电流 (GIMIC) 方法获得的芳香指数进行了比较。然而,TRE 芳香指数与 GIMIC 芳香指数之间缺乏相关性,而且观察到的趋势相互矛盾,这表明有必要进行进一步研究,以全面了解杂[8]环烯的芳香性。我们采用了电路共振能量 (CRE) 方法来评估局部芳香性。我们的 CRE 结果表明,分子中的单个苯或杂环五元单元在中性和双电荷离子状态下都能保持其强烈的芳香特性,并成为全局芳香性的主要来源。尽管我们的 CRE 结果提供了有价值的见解,但必须注意的是,在有些情况下,核无关化学位移(NICS[0] 和 NICS[1])指数预测的局部芳香性大小与我们的 CRE 结果并不一致。
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来源期刊
CiteScore
3.60
自引率
11.10%
发文量
161
审稿时长
2.3 months
期刊介绍: The Journal of Physical Organic Chemistry is the foremost international journal devoted to the relationship between molecular structure and chemical reactivity in organic systems. It publishes Research Articles, Reviews and Mini Reviews based on research striving to understand the principles governing chemical structures in relation to activity and transformation with physical and mathematical rigor, using results derived from experimental and computational methods. Physical Organic Chemistry is a central and fundamental field with multiple applications in fields such as molecular recognition, supramolecular chemistry, catalysis, photochemistry, biological and material sciences, nanotechnology and surface science.
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