Work

Singlet/Triplet State Anti/Aromaticity of CyclopentadienylCation: Sensitivity to Substituent Effect

Year: 2021

Type: article

Abstract: 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.

Source: Chemistry

DOI: 10.3390/chemistry3030055

Authors: Milovan Stojanović, Jovana Aleksić, Marija Baranac-Stojanović

Institutions: University of Belgrade, Institute of Chemistry, Technology and Metallurgy

Language: English

Topic: Synthesis and Properties of Aromatic Compounds

Subfield: Organic Chemistry

Field: Chemistry

Domain: Physical Sciences

Open Access status: gold

Estimated APC paid: $1,296

Funder: Ministarstvo Prosvete, Nauke i Tehnološkog Razvoja