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

Asadov, Ziyafaddin H.; Ahmadova, Gulnara A.; Rahimov, Ravan A.; Hashimzade, Seyid-Zeynab F.; Abdullayev, Yusif; Ismailov, Etibar H.; Suleymanova, Samira A.; Asadova, Nahida Z.; Zubkov, Fedor I.; Autschbach, Jochen

doi:10.1016/j.molliq.2020.112579

Cited by 15 publications

(12 citation statements)

References 34 publications

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“…Concerted TS CAT_FREE is obtained for the one-step direct transformation of EtNH 2 and 2,3-methyloxirane to 3-(ethylamino)butan-2-ol (PRO) via 54.2 kcal/mol energy barrier. A similar energy barrier was calculated previously for the epoxide ring-opening in catalyst-free condition [46]. The calculated energy barrier shows that utilizing a catalyst will be a cost-effective option for the process.…”

Section: Epoxide Ring-openingsupporting

confidence: 79%

Computational mechanistic studies of the carbon–carbon double bond difunctionalization via epoxidation and subsequent aminolysis in vegetable oils

Abdullayev

Abbasov

Nasirov

et al. 2021

Int J of Quantum Chemistry

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The industrial importance of the C C double bond difunctionalization in vegetable oils/fatty acid chains motivates computational studies aimed at helping to improve experimental protocols. The C C double bond epoxidation is studied with hydrogen peroxide, peracetic acid (CH 3 CO 3 H), and performic acid (HCO 3 H) oxidizing agents. The epoxide ring-opening mechanism is calculated in the presence of ZnCl 2 , NiCl 2 , and FeCl 2 Lewis acidic catalysts. Computations show that H 2 O 2 (ΔG ‡ = 39 kcal/mol, TS1 HP) is not an effective oxidizing agent compared to CH 3 CO 3 H (ΔG ‡ = 29.8 kcal/ mol, TS1 PA) and HCO 3 H (ΔG ‡ = 26.7 kcal/mol, TS1 PF). The FeCl 2 (ΔG ‡ = 14.7 kcal/ mol, TS1 FC) coordination to the epoxide oxygen facilitates the ring-opening via lower energy barriers compared to the ZnCl 2 (ΔG ‡ = 19.5 kcal/mol, TS1 ZC) and NiCl 2 (ΔG ‡ = 29.4 kcal/mol, TS1 NC) coordination. ZnCl 2 was frequently utilized as a catalyst in laboratory-scale procedures. The energetic span model identifies the FeCl 2 (FC) catalytic cycle as the best option for the epoxide ring-opening.

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Section: Epoxide Ring-openingsupporting

confidence: 79%

Computational mechanistic studies of the carbon–carbon double bond difunctionalization via epoxidation and subsequent aminolysis in vegetable oils

Abdullayev

Abbasov

Nasirov

et al. 2021

Int J of Quantum Chemistry

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“…When a spacer is a methylene group, the length of the spacer induces nonpolarity in the otherwise polar Gemini head group. Thus, replacing “–(CH 2 ) 2 -” with “–(CH 2 ) 6 -” is expected to introduce a significant nonpolarity in the tetraalkylammonium dimeric head group of 16-6-16. ,− This enhanced nonpolarity in fact has a pronounced influence on the variation of intensity of both Ag/Au NPs (Figure a, inset). It shows now a regular fall in contrast to that as shown in Figure c inset, where it goes through the colloidal stabilization for both Ag/Au NPs.…”

Section: Resultsmentioning

confidence: 99%

Mechanistic Aspects of Simultaneous Extraction of Silver and Gold Nanoparticles across Aqueous–Organic Interfaces by Surface Active Iron Oxide Nanoparticles

Kaur

Bakshi

2020

Langmuir

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Surface active iron oxide nanoparticles (NPs) were used for the simultaneous extraction of water soluble Ag and Au NPs across an aqueous− organic interface from aqueous bulk. The surface activity of iron oxide NPs was achieved by using cationic Gemini surfactants of different architectures during the in situ synthesis of iron oxide NPs in hydrothermal synthesis. Aqueous bulk solubility of Ag and Au NPs was achieved by stabilizing them with conventional surfactants of different polarities such as SDS, CTAB, and DDM. The amphiphilic nature of iron oxide NPs demonstrated their remarkable ability to extract Ag and Au NPs through both hydrophilic and hydrophobic interactions. The mechanism of extraction from aqueous bulk was monitored by placing different amounts of surface active iron oxide NPs on the aqueous−organic interface and was studied with the help of UV−visible, DLS, and IR measurements. XPS and TEM measurements were used for the quantitative estimation of efficiency of extraction. Extraction was facilitated when both hydrophilic and hydrophobic interactions were participating simultaneously. Results may help in designing a suitable method for purification of industrial effluents contaminated with metal particulates simply by applying an external magnetic field rather than going through a complicated conventional filtration process.

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“…The balance between hydrophobic and hydrophilic parts, and the hydrophilic-lipophilic balance, is responsible for the self-assembly process of these amphiphilic compounds in solutions [ 2 ]. It affects the properties of the compounds, which generates their use in many areas of life and industry, starting from cleaning agents and detergents [ 3 , 4 , 5 , 6 ], through to protective applications such as antimicrobials [ 7 , 8 , 9 , 10 ] or anticorrosion products [ 11 , 12 , 13 , 14 , 15 ], to modern biomedical applications [ 16 , 17 , 18 , 19 , 20 , 21 ] or enhanced oil recovery [ 22 , 23 , 24 , 25 , 26 ]. Surfactants may also have two hydrocarbon chains attached to a polar head and are named double chain surfactants.…”

Section: Introductionmentioning

confidence: 99%

Fabrication of Encapsulated Gemini Surfactants

et al. 2022

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(1) Background: Encapsulation of surfactants is an innovative approach that allows not only protection of the active substance, but also its controlled and gradual release. This is primarily used to protect metallic surfaces against corrosion or to create biologically active surfaces. Gemini surfactants are known for their excellent anticorrosion, antimicrobial and surface properties; (2) Methods: In this study, we present an efficient methods of preparation of encapsulated gemini surfactants in form of alginate and gelatin capsules; (3) Results: The analysis of infrared spectra and images of the scanning electron microscope confirm the effectiveness of encapsulation; (4) Conclusions: Gemini surfactants in encapsulated form are promising candidates for corrosion inhibitors and antimicrobials with the possibility of protecting the active substance against environmental factors and the possibility of controlled outflow.

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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

Cited by 15 publications

References 34 publications

Computational mechanistic studies of the carbon–carbon double bond difunctionalization via epoxidation and subsequent aminolysis in vegetable oils

Computational mechanistic studies of the carbon–carbon double bond difunctionalization via epoxidation and subsequent aminolysis in vegetable oils

Mechanistic Aspects of Simultaneous Extraction of Silver and Gold Nanoparticles across Aqueous–Organic Interfaces by Surface Active Iron Oxide Nanoparticles

Fabrication of Encapsulated Gemini Surfactants

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