Structures and electron affinity energies of polycyclic quinones

• Published in: Heliyon 2022-08, Vol.8 (8), p.e10107-e10107, Article e10107
• Main Authors: Wang, Xucheng, Cheng, Yao, Yuan, Yaofeng, Zhang, Yongfan, Wang, Wenfeng
• Format: Article
• Language: English
• Subjects: Calculation; Crystal structure; Electron affinity energy; hydrogen; imidazole; Polycyclic quinones; pyrazines; pyrroles; quinones
• ISSN: 2405-8440; 2405-8440
• DOI: 10.1016/j.heliyon.2022.e10107

In this study, quinoid structures, semiquinone radical structures, and electron affinity energies (EAEs) of many polycyclic quinones containing heteroatoms (O, B, and F) or heterocycles (pyrrole, imidazole, and pyrazine) were calculated. Quinones with unstable quinoid structures and stable semiquinone radical structures had high EAEs. The main factors of quinoid structural instability were spatial repulsion and antiaromaticity, and the stability factors of the semiquinone radical structure comprised inductive effects, hydrogen bonds, electrostatic interactions, and orbital interactions. Compound 11 had both the antiaromaticity of the quinoid structure and the orbital interactions of the semiquinone radical structure, thus having the highest EAE. The crystal structure of compound 8 was obtained, and it confirmed the reliability of the calculated results of this work. •The relationship between electron affinity energy and many factors is revealed.•The close relationship between the electronic structure and the spatial structure is revealed.•Various interactions such as orbital, electrostatic, and spatial repulsion are exhibited. Polycyclic quinones; Electron affinity energy; Crystal structure; Calculation.