Density functional theory study on 1-substituted-2-hydroxyaminobenzimidazole derivatives

• Published in: Zhejiang da xue xue bao. Journal of Zhejiang University. Sciences edition. Li xue ban Vol. 38; no. 1; pp. 58 - 62
• Main Authors: Xie, Hu-Jun, Hu, Xiao-Huan, Shao, Shuang, Lei, Qun-Fang, Xuan, Gui-Da
• Format: Journal Article
• Language: Chinese
• Published: Zhejiang University Press 01.02.2011
• Subjects: 1-取代-2-羟氨苯并咪唑衍生物; Density; Derivatives; Imidazole; Mathematical analysis; Metabolism; Oxidation; Quantum chemistry; Toxicity; 密度泛函理论; 能量分析; 自然键轨道
• ISSN: 1008-9497
• DOI: 10.3785/j.issn.1008-9497.2011.01.015

1-Substituted-2-hydroxyaminobenzimidazoles with high toxicity are unstable intermediates potentially produced during the oxidation metabolism of 1-substituted-2-aminobenzimidazoles. The quantum chemical calculation of density functional theory(DFT) has been performed to investigate the electronic structure and properties of eight kinds of 1-substituted-2-hydroxyaminobenzimidazole derivatives. It follows that the substituted groups have significant effects on the C-N bond length and the charge on N atoms of the imidazole ring. In addition, the substituted groups are responsible for the obvious variation of dipole moment, vertical ionization potential, vertical electron affinity, chemical potential, electronegativity, and electronphilicity, which are related to the toxicity of the derivatives. The calculated absorption and excitation spectra indicate that the increase values of vertical transition energy, the decrease of the oscillator strength and the blue shift of the maximum absorption wavelength are observe