Singlet/Triplet State Anti/Aromaticity of CyclopentadienylCation: Sensitivity to Substituent Effect
| Autor: | Milovan Stojanovic, Jovana Aleksić, Marija Baranac-Stojanović |
|---|---|
| Jazyk: | angličtina |
| Rok vydání: | 2021 |
| Předmět: |
singlet state
Substituent triplet state 010402 general chemistry 01 natural sciences chemistry.chemical_compound Cyclopentadienyl complex Computational chemistry Physics::Atomic and Molecular Clusters Singlet state Triplet state Physics::Chemical Physics Benzene QD1-999 010405 organic chemistry Aromaticity General Medicine aromaticity antiaromaticity 0104 chemical sciences Chemistry chemistry cyclopentadienyl cation Density functional theory substituent effect Antiaromaticity |
| Zdroj: | Chemistry, Vol 3, Iss 55, Pp 765-782 (2021) Chemistry Volume 3 Issue 3 Pages 55-782 |
| ISSN: | 2624-8549 |
| Popis: | It is well known that singlet state aromaticity is quite insensitive to substituent effects, in the case of monosubstitution. In this work, we use density functional theory (DFT) calculations to examine the sensitivity of triplet state aromaticity to substituent effects. For this purpose, we chose the singlet state antiaromatic cyclopentadienyl cation, antiaromaticity of which reverses to triplet state aromaticity, conforming to Baird’s rule. The extent of (anti)aromaticity was evaluated by using structural (HOMA), magnetic (NICS), energetic (ISE), and electronic (EDDBp) criteria. We find that the extent of triplet state aromaticity of monosubstituted cyclopentadienyl cations is weaker than the singlet state aromaticity of benzene and is, thus, slightly more sensitive to substituent effects. As an addition to the existing literature data, we also discuss substituent effects on singlet state antiaromaticity of cyclopentadienyl cation. |
| Databáze: | OpenAIRE |
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