Aromaticity study of singlet- and triplet-state corannulene dianion and dication,Journal of Physical Organic Chemistry

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Aromaticity study of singlet- and triplet-state corannulene dianion and dication
Journal of Physical Organic Chemistry ( IF 1.9 ) Pub Date : 2022-09-13 , DOI: 10.1002/poc.4434
Jovana Aleksić ₁ , Milovan Stojanović ₁ , Marija Baranac‐Stojanović ₂

Affiliation

Aromaticity rules in the ground singlet state and the first excited triplet state are exactly opposite, as shown by Baird. Thus, (4n + 2)π electron annulenes are antiaromatic and 4nπ annulenes are aromatic in their triplet state. In this work, we employ quantum-mechanical calculations at the density functional theory (DFT) level to examine (anti)aromaticity of singlet and triplet corannulene dianion and dication in their bowl-shaped ground-state structure and planar transition-state structure. We find that singlet dianion contains aromatic hub and antiaromatic rim, whereas singlet dication is an antiaromatic system. This agrees with previous calculations of current density induced by perpendicular magnetic field. For triplet dianion, we find that it can be described as having aromatic rim and nonaromatic hub. Triplet dication was found to be nonaromatic, though in planar transition-state structure, locally and semiglobally antiaromatic naphthalene subunit and aromatic central ring can be discerned.

中文翻译：

单线态和三线态环烯双阴离子和双阳离子的芳香性研究

如 Baird 所示，基单重态和第一激发三重态的芳香性规则恰好相反。因此，(4n + 2)π 电子环烯在三重态时是反芳香的，而 4nπ 环烯是芳香的。在这项工作中，我们在密度泛函理论 (DFT) 水平上采用量子力学计算来检查单线态和三线态环烯双阴离子的（反）芳香性以及碗状基态结构和平面过渡态结构中的双阳离子。我们发现单线态二价阴离子包含芳香中心和反芳香环，而单线态二价阳离子是一个反芳香系统。这与先前对垂直磁场感应的电流密度的计算一致。对于三重态二价阴离子，我们发现它可以描述为具有芳香环和非芳香环。

更新日期：2022-09-13

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