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Hückel Molecular Orbital Analysis for Stability and Instability of Stacked Aromatic and Stacked Antiaromatic Systems
The Journal of Organic Chemistry ( IF 3.3 ) Pub Date : 2023-10-16 , DOI: 10.1021/acs.joc.3c01167 Yuta Tsuji 1 , Kazuki Okazawa 2 , Kazunari Yoshizawa 2
The Journal of Organic Chemistry ( IF 3.3 ) Pub Date : 2023-10-16 , DOI: 10.1021/acs.joc.3c01167 Yuta Tsuji 1 , Kazuki Okazawa 2 , Kazunari Yoshizawa 2
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Face-to-face stacking of aromatic compounds leads to stacked antiaromaticity, while that of antiaromatic compounds leads to stacked aromaticity. This is a prediction with a long history; in the late 2000s, the prediction was confirmed by high-precision quantum chemical calculations, and finally, in 2016, a π-conjugated system with stacked aromaticity was synthesized. Several variations have since been reported, but essentially, they are all the same molecule. To realize stacked aromaticity in a completely new and different molecular system and to trigger an extension of the concept of stacked aromaticity, it is important to understand the origin of stacked aromaticity. The Hückel method, which has been successful in giving qualitatively correct results for π-conjugated systems despite its bold assumptions, is well suited for the analysis of stacked aromaticity. We use this method to model the face-to-face stacking systems of benzene and cyclobutadiene molecules and discuss their stacked antiaromaticity and stacked aromaticity on the basis of their π-electron energies. By further developing the discussion, we search for clues to realize stacked aromaticity in synthesizable molecular systems.
中文翻译：
堆积芳香族和堆积反芳香族体系稳定性和不稳定性的 Hückel 分子轨道分析
芳香族化合物面对面堆积导致堆积反芳香性，而反芳香性化合物面对面堆积导致堆积芳香性。这是一个有着悠久历史的预言；2000年代末，高精度量子化学计算证实了这一预测，并最终在2016年合成了具有堆叠芳香性的π共轭体系。此后已报道了几种变体，但本质上，它们都是相同的分子。为了在全新的不同分子系统中实现堆叠芳香性并引发堆叠芳香性概念的扩展，了解堆叠芳香性的起源非常重要。Hückel 方法尽管假设大胆，但已成功为 π 共轭体系提供了定性正确的结果，非常适合堆叠芳香性的分析。我们使用这种方法对苯和环丁二烯分子的面对面堆叠系统进行建模，并根据它们的π电子能量讨论它们的堆叠反芳香性和堆叠芳香性。通过进一步展开讨论，我们寻找在可合成分子系统中实现堆叠芳香性的线索。
更新日期：2023-10-16
中文翻译：
堆积芳香族和堆积反芳香族体系稳定性和不稳定性的 Hückel 分子轨道分析
芳香族化合物面对面堆积导致堆积反芳香性，而反芳香性化合物面对面堆积导致堆积芳香性。这是一个有着悠久历史的预言；2000年代末，高精度量子化学计算证实了这一预测，并最终在2016年合成了具有堆叠芳香性的π共轭体系。此后已报道了几种变体，但本质上，它们都是相同的分子。为了在全新的不同分子系统中实现堆叠芳香性并引发堆叠芳香性概念的扩展，了解堆叠芳香性的起源非常重要。Hückel 方法尽管假设大胆，但已成功为 π 共轭体系提供了定性正确的结果，非常适合堆叠芳香性的分析。我们使用这种方法对苯和环丁二烯分子的面对面堆叠系统进行建模，并根据它们的π电子能量讨论它们的堆叠反芳香性和堆叠芳香性。通过进一步展开讨论，我们寻找在可合成分子系统中实现堆叠芳香性的线索。
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