Structures and electron affinity energies of polycyclic quinones

Xucheng Wang; Yao Cheng; Yaofeng Yuan; Yongfan Zhang; Wenfeng Wang

doi:10.1016/j.heliyon.2022.e10107

Structures and electron affinity energies of polycyclic quinones

Heliyon. 2022 Aug 5;8(8):e10107. doi: 10.1016/j.heliyon.2022.e10107. eCollection 2022 Aug.

Authors

Xucheng Wang¹, Yao Cheng¹, Yaofeng Yuan¹, Yongfan Zhang¹, Wenfeng Wang¹

Affiliation

¹ Key Laboratory of Molecule Synthesis and Function Discovery, Fuzhou University, Fuzhou 350116, China.

Abstract

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.

Keywords: Calculation; Crystal structure; Electron affinity energy; Polycyclic quinones.