文献类型：期刊文献

英文题名：Concise CuI-catalyzed azide-alkyne 1,3-dipolar cycloaddition reaction ligation remarkably enhances the corrosion inhibitive potency of natural amino acids for mild steel in HCl

作者：Deng, Qiong[1]; He, Xiao-Peng[1]; Shi, Hong-Wei[3]; Chen, Bao-Qin[1]; Liu, Guixia[3]; Tang, Yun[3]; Long, Yi-Tao[1,2]; Chen, Guo-Rong[1]; Chen, Kaixian[1]

机构：[1] Key Laboratory for Advanced Materials, Institute of Fine Chemicals, China; [2] State Key Laboratory of Bioreactor Engineering, School of Pharmacy, East China University of Science and Technology, Shanghai 200237, China; [3] Shanghai Key Laboratory of New Drug Design, School of Pharmacy, East China University of Science and Technology, Shanghai 200237, China

年份：2012

卷号：51

期号：21

起止页码：7160

外文期刊名：Industrial and Engineering Chemistry Research

收录：EI(收录号：20124015534649)

语种：英文

外文关键词：Corrosion inhibitors - Low carbon steel - Quantum chemistry - Amino acids - Steel corrosion - Copper compounds - Electrochemical impedance spectroscopy - Electrochemical corrosion - Catalysis - Copper corrosion - Cycloaddition - Hydrocarbons

摘要：Despite natural amino acids having been proposed as the green surrogate of currently used corrosion inhibitors that are generally toxic to both nature and human body during the everyday industrial processing of metallic equipments, their structural simplicity yet lowers the inhibitive potency, thereby hampering their further industrialization. We disclose here that a concise chemical ligation (CuI-catalyzed azide-alkyne 1,3-dipolar cycloaddition reaction [Cue-AAC]) between two L-amino acids that are weak or noncorrosion inhibitors may result in their largely improved protective effect for mild steel in HCl. A series of 1,4-disubstituted 1,2,3-triazolyl bis-amino acid derivatives constituted by L-serine, L-threonine, L-phenylalanine, and L-tyrosine were efficiently synthesized via Cue-AAC and deprotection reactions in high yields. Subsequently performed electrochemical impedance spectroscopy (EIS) evidenced that the inhibitive effect of these compounds for mild steel in 1 M HCl is markedly better than that of their natural amino acid counterparts. The inhibitive modality of the most potent inhibitor was interpreted in detail by potentiodynamic polarization and thermodynamic calculations. Furthermore, quantum chemical calculations suggest that the triazole ring formed by the Cue-AAC has contribution to their metal surface adsorption. This study would offer unique insights into the facile development of potency-enhanced green corrosion inhibitors based on the concise Cue-AAC ligation of natural amino acids. ? 2012 American Chemical Society.