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Aggregation and antimicrobial properties of gemini surfactants with mono- and di-(2-hydroxypropyl)ammonium head-groups: Effect of the spacer length and computational studies
Journal of Molecular Liquids ( IF 6 ) Pub Date : 2020-01-27 , DOI: 10.1016/j.molliq.2020.112579
Ziyafaddin H. Asadov , Gulnara A. Ahmadova , Ravan A. Rahimov , Seyid-Zeynab F. Hashimzade , Yusif Abdullayev , Etibar H. Ismailov , Samira A. Suleymanova , Nahida Z. Asadova , Fedor I. Zubkov , Jochen Autschbach

Cationic gemini surfactants, alkanediyl-α,ω-bis[(2-hydroxypropyl)dodecylammonium] dibromide (abbreviated as C12-s-C12[iso-Pr(OH)] and C12-s-C12[iso-Pr(OH)]2, with s = 2, 3, 4 and 5) have been synthesized, and their aggregation properties in aqueous solution have been studied by surface tension, electrical conductivity and dynamic light scattering methods. On the basis of the results of studying aqueous solutions of the synthesized gemini surfactants by tensiometric and conductometric methods, their principal surfactivity parameters, such as the degree of counterion binding (β), critical micelle concentration (CMC), effectiveness of surface tension reduction (πCMC), surface excess concentration (Γmax), area per molecule at the interface (Amin), changes of Gibbs free energies of adsorption (ΔGad) and micellization (ΔGmic) have been calculated. For both classes of these gemini surfactants, a character of the surfactivity parameters change with an elongation of the spacer chain was defined and comparative analysis with other ammonium-type gemini surfactants having different head-groups was performed. Using dynamic light scattering method, regularities of variation of the aggregates sizes were studied depending on the number of 2-hydroxypropyl groups and the spacer chain length was investigated. Meanwhile, it was revealed that the mentioned gemini surfactants possess antimicrobial properties. The mechanism of the epoxide ring opening and salt formation reactions were calculated by using Kohn–Sham DFT with the B3LYP functional. The epoxide ring opening via primary (dodecylamine) and secondary (INT2) amines was determined as exergonic (13.4 and 4.4 kcal/mol) reactions as observed experimentally.



中文翻译:

具有单和二(2-羟丙基)铵头基的双子表面活性剂的聚集和抗菌性能:间隔物长度的影响和计算研究

阳离子双子表面活性剂,烷二基-α,ω-双[(2-羟丙基)十二烷基铵]二溴化物(缩写为C 12 -sC 12 [iso-Pr(OH)]和C 12 -sC 12 [iso-Pr(OH)]已经合成了具有2,s = 2、3、4和5的2),并且通过表面张力,电导率和动态光散射方法研究了它们在水溶液中的聚集性质。在通过拉力法和电导法研究合成双子表面活性剂水溶液的结果的基础上,它们的主要表面活性参数,如抗衡离子结合度(β),临界胶束浓度(CMC),表面张力降低的有效性( π CMC),表面过量浓度(Γ最大),在界面处(A每分子面积分钟),吸附(ΔG的吉布斯自由能的变化广告)和胶束(ΔG麦克风)已计算。对于这两类双子表面活性剂,定义了表面活性参数随间隔链的延长而变化的特征,并且与具有不同首基的其他铵型双子表面活性剂进行了比较分析。使用动态光散射方法,研究了取决于2-羟丙基基团数目的聚集体尺寸变化规律,并研究了间隔链长度。同时,发现上述双子表面活性剂具有抗菌性能。通过使用具有B3LYP功能的Kohn-Sham DFT,可以计算出环氧化物开环和成盐反应的机理。通过伯(十二烷基胺)和仲(INT2如实验观察到的那样,胺被确定为能效反应(13.4和4.4 kcal / mol)。

更新日期:2020-01-27
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