Aggregation and antimicrobial properties of gemini surfactants with mono- and di-(2-hydroxypropyl)ammonium head-groups: Effect of the spacer length and computational studies

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. © 2020 Elsevier B.V.

Asadov Z.H.1 , Ahmadova G.A.1 , Rahimov R.A. 1, 2 , Hashimzade S.-Z.F.1 , Abdullayev Y.1, 2 , Ismailov E.H.3 , Suleymanova S.A.1 , Asadova N.Z.4 , Zubkov F.I. 5 , Autschbach J.6
Elsevier B.V.
  • 1 Institute of Petrochemical Processes of Azerbaijan National Academy of Sciences, Hojaly ave. 30, Baku, AZ 1025, Azerbaijan
  • 2 Department of Chemical Engineering, Baku Engineering University, Hasan Aliyev str. 120, Baku, Absheron AZ0101, Azerbaijan
  • 3 Institute of Catalysis and Inorganic Chemistry, National Academy of Sciences of Azerbaijan, H. Cavid ave. 113, Baku, AZ 1143, Azerbaijan
  • 4 Faculty of Biology, Baku State University, Z. Khalilov St. 23, Baku, AZ 1148, Azerbaijan
  • 5 Organic Chemistry Department, Faculty of Science, Peoples' Friendship University of Russia (RUDN University), 6 Miklukho-Maklaya St., Moscow, 117198, Russian Federation
  • 6 Department of Chemistry, University at Buffalo, State University of New York, Buffalo, NY 14260-3000, United States
Adsorption; Antimicrobial properties; Gemini surfactant; Micellization; Surface tension
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