Key Laboratory for Advanced Materials & Institute of Fine Chemicals, East China University of Science and Technology, 130 Meilong Road, Shanghai 200237, PR China.
Carbohydr Res. 2012 Jun 1;354:32-9. doi: 10.1016/j.carres.2012.03.006. Epub 2012 Mar 17.
Triazolyl glycolipid derivatives constructed via Cu(I)-catalyzed azide-alkyne 1,3-dipolar cycloaddition reaction (Cue-AAC) represent a new range of carbohydrate-based scaffolds for use in many fields of the chemical research. Here the surface adsorptive ability of series of our previously prepared C1- or C6-triazole linked gluco- and galactolipid derivatives for mild steel in 1 M HCl was studied via electrochemical impedance spectroscopy (EIS). Results indicated that these monosaccharide-fatty acid conjugates are weak inhibitors against HCl corrosion for mild steel. Moreover, some newly synthesized triazolyl disaccharide (maltose)-fatty alcohol conjugates failed to display enhanced activity, meaning that the structural enlargement of the sugar moiety does not favor the iron surface adsorption. However, a bis-triazolyl glycolipid derivative, which was realized by introducing a benzenesulfonamide group via Cue-AAC to the C6-position of a C1-triazolyl glucolipid analog, eventually showed significantly improved adsorptive potency compared to that of its former counterparts. The corrosion inhibitive modality of this compound for mild steel in HCl was subsequently studied via potentiodynamic polarization and thermodynamic calculations.
通过 Cu(I)-催化的叠氮-炔 1,3-偶极环加成反应 (CuAAC) 构建的三唑基糖脂衍生物代表了一类新型的基于碳水化合物的支架,可用于化学研究的许多领域。在此,通过电化学阻抗谱 (EIS) 研究了一系列先前制备的 C1-或 C6-三唑连接的葡萄糖和半乳糖脂衍生物在 1 M HCl 中对低碳钢的表面吸附能力。结果表明,这些单糖-脂肪酸缀合物对低碳钢在 HCl 腐蚀中的抑制作用较弱。此外,一些新合成的三唑基二糖(麦芽糖)-脂肪醇缀合物未能显示出增强的活性,这意味着糖部分的结构增大不利于铁表面吸附。然而,通过 Cue-AAC 将苯磺酰胺基团引入到 C1-三唑基葡糖苷类似物的 C6-位,最终得到的双三唑基糖脂衍生物显示出比其前体显著提高的吸附能力。随后通过动电位极化和热力学计算研究了该化合物在 HCl 中对低碳钢的腐蚀抑制模式。