Aromaticity study of singlet- and triplet-state corannulene dianion and dication
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2022
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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.
Ključne reči:
aromaticity / Baird rule / corannulene dianion / corannulene dication / Hückel rule / triplet stateIzvor:
Journal of Physical Organic Chemistry, 2022Izdavač:
- John Wiley and Sons Ltd
Finansiranje / projekti:
DOI: 10.1002/poc.4434
ISSN: 0894-3230; 1099-1395
WoS: 000855129500001
Scopus: 2-s2.0-85138258777
Institucija/grupa
IHTMTY - JOUR AU - Aleksić, Jovana AU - Stojanović, Milovan AU - Baranac-Stojanović, Marija PY - 2022 UR - https://cer.ihtm.bg.ac.rs/handle/123456789/5365 AB - 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. PB - John Wiley and Sons Ltd T2 - Journal of Physical Organic Chemistry T1 - Aromaticity study of singlet- and triplet-state corannulene dianion and dication DO - 10.1002/poc.4434 ER -
@article{ author = "Aleksić, Jovana and Stojanović, Milovan and Baranac-Stojanović, Marija", year = "2022", abstract = "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.", publisher = "John Wiley and Sons Ltd", journal = "Journal of Physical Organic Chemistry", title = "Aromaticity study of singlet- and triplet-state corannulene dianion and dication", doi = "10.1002/poc.4434" }
Aleksić, J., Stojanović, M.,& Baranac-Stojanović, M.. (2022). Aromaticity study of singlet- and triplet-state corannulene dianion and dication. in Journal of Physical Organic Chemistry John Wiley and Sons Ltd.. https://doi.org/10.1002/poc.4434
Aleksić J, Stojanović M, Baranac-Stojanović M. Aromaticity study of singlet- and triplet-state corannulene dianion and dication. in Journal of Physical Organic Chemistry. 2022;. doi:10.1002/poc.4434 .
Aleksić, Jovana, Stojanović, Milovan, Baranac-Stojanović, Marija, "Aromaticity study of singlet- and triplet-state corannulene dianion and dication" in Journal of Physical Organic Chemistry (2022), https://doi.org/10.1002/poc.4434 . .