Role of an Amide Bond for Self-Assembly of Surfactants

Bordes, Romain; Tropsch, Juergen; Holmberg, Krister

doi:10.1021/la902979m

Cited by 101 publications

(67 citation statements)

References 33 publications

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“…Interactions with the Cu surface are apparently due not only to the hydrophobic properties of a molecule but also to the presence of heteroatoms (particularly nitrogen) in its composition or multiple bonds that can form both additional intermolecular bonds between particles of an adsorbate such as SOS and other bonds with the metal surface being protected. Results obtained by other investigators [40,41] are in favor of this version. These investigations demonstrated the impact of the tail groups of SOS molecules on interactions with metal surfaces.…”

mentioning

confidence: 70%

“…These investigations demonstrated the impact of the tail groups of SOS molecules on interactions with metal surfaces. For example, the role of amide bonds in the selforganization of surfactants on a gold surface was revealed in [40]. It was shown that sarcosine derivatives form chelate compounds with a metal surface that can induce the polymolecular adsorption of SOS molecules.…”

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confidence: 99%

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Organic corrosion inhibitors: where are we now? A review. Part II. Passivation and the role of chemical structure of carboxylates

Kuznetsov

2016

Int. J. Corros. Scale Inhib.

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This article provides an overview of works (2006)(2007)(2008)(2009)(2010)(2011)(2012)(2013)(2014)(2015)(2016) devoted to the passivation of various metals and the influence of organic carboxylic acids and their salts thereon. The results of corrosion and electrochemical studies, as well studies on the composition and structural features of surface layers on the metals being protected by a variety of physicochemical methods are considered. Protection of metals by organic corrosion inhibitors (CIs) is based mostly on the adsorption of these compounds on a metal surface and subsequent formation of protective layers that minimizes access of corrosive ions to that surface. Adsorption can occur via electrostatic interaction of the CI with the metal substrate (physisorption), or it can involve charge sharing between the surface and CI (chemisorption), or combination of both interaction types can take place. Passivation of metals remains a central problem to be solved by the corrosion science. In the development of nanoindustry methods focused on creating ultrathin layers on metals capable of preventing the corrosion of the metals, an important role is played by surface passivation using CIs. Corrosion inhibitors can form passivating (often polymolecular) layers on metals but with thickness d < 10 nm, making them invisible to an unaided eye and keeping intact the decorative properties of a coated article's surface. This passivation can be done using volatile CIs from the vapor phase or nonvolatile CIs from aqueous solutions. Since metal passivation using conventional corrosion inhibitors of oxidizing type (e.g., nitrites, chromates) is seriously limited in practice due to environmental considerations, requirements for inhibiting formulations keep changing over time.The use of corrosion inhibitors in passivation has played a major role not only in the application of oxidants (chromates, nitrites, etc.) but also in adsorptive, often "oxideless" passivation that we discovered as early as in the mid-1970s [1]. As for corrosion inhibitors

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confidence: 70%

mentioning

confidence: 99%

Organic corrosion inhibitors: where are we now? A review. Part II. Passivation and the role of chemical structure of carboxylates

Kuznetsov

2016

Int. J. Corros. Scale Inhib.

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“…The micellar association of amphiphilic molecules in water is the result of a delicate balance between hydrophobic and hydrophilic forces. In micelles, the polar head groups align at the micelle-water interface, while the non-polar hydrocarbon chains interact with one another in the micelle core [11][12][13]. This micelle structure is dynamic, with surfactant molecules free to & Kevin F. Morris kmorris@carthage.edu exchange between the micelle and free solution.…”

Section: Introductionmentioning

confidence: 99%

“…Above the CMC, van der Waals interactions between the surfactants' hydrocarbon tails favor micellization, while the repulsion of the polar head groups opposes self-assembly [11,12]. In addition, the atoms in functional groups, like the amide bond found in amino acid-based surfactants, often form intermolecular hydrogen bonds that in turn play an important role in determining the size and shape of surfactant micelles [11][12][13]. Amino acid-based surfactants have become increasingly popular in recent years because they are environmentally benign, abundant, and quite versatile [11][12][13][14][15][16][17][18][19].…”

Section: Introductionmentioning

confidence: 99%

Effect of pH on the Binding of Sodium, Lysine, and Arginine Counterions to l‐Undecyl Leucinate Micelles

Lewis

Hughes

Vasquez

et al. 2016

J Surfact & Detergents

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Micelle formation by the amino acid‐based surfactant undecylenyl l‐leucine was investigated as a function of solution pH with NMR, dynamic light scattering, and fluorescence spectroscopy. NMR and dynamic light scattering showed that 50 mM undecylenyl l‐leucine and 50 mM NaHCO3 solutions contained micelles approximately 20 Å in diameter and that micelle radius and the mole fraction of surfactant molecules associated with micelles changed very little with solution pH. The binding of the amino acids arginine and lysine to the anionic micelles was also investigated from pH 7.0 to 11.5. Below pH 9.0, the mole fraction of arginine cations bound to the micelles was approximately 0.4. Above pH 9.0, the arginine counterions became zwitterionic, and the mole fraction of bound arginine molecules decreased steadily to less than 0.1 at pH 11. When arginine dissociated from the micelles, their radii decreased from 14 to 10 Å. Similar behavior was observed with lysine; however, when lysine dissociated from the micelle surface, little change in micelle radius was observed. Two‐dimensional NMR experiments suggested that below pH 9.0, l‐arginine bound perpendicular to the micelle surface primarily though its side chain amine while l‐lysine bound parallel to the surface through both of its amine functional groups. Finally, the rate at which the amide protons on the surfactant headgoup exchanged with solvent was investigated with NMR spectroscopy. The exchange reaction was faster in solutions containing only surfactant monomers and slower when the surfactants were in micellar form and the headgoup amide protons were less exposed to solvent.

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“…For example, aminophosphonates [12], amides [13] and urea [14] on the particle surface are expected to facilitate the assembly, amine groups can also be used to introduce charge on the surface [15]. Our goal is to create materials based on such silica nanoparticles with potential applications in sensing, separations of biologically relevant molecules and drug delivery.…”

Section: Introductionmentioning

confidence: 99%

Silica Nanoparticles with Proton Donor and Proton Acceptor Groups: Synthesis and Aggregation

Gorbachuk

Yakimova

Mostovaya

et al. 2011

Silicon

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The effects of precursor structure and polycondensation conditions on the properties of hybrid nanoparticles synthesized from organo-trimethoxysilanes were studied. Hybrid nanoparticles containing groups capable of forming hydrogen bonds were synthesized from functional derivatives of 3-aminopropyltrimethoxysilane. For the synthesis of phenylurea-functionalized organosilica nanoparticles different approaches to nanoparticle preparation were used. It was shown that the nature of the functional groups (proton-donor or proton-acceptor) affects the aggregation of silica nanoparticles. Also, the difference in behavior of nanoparticles prepared using surface modification and polycondensation was demonstrated for different pH, ionic strength and solvent polarity. As a result, by changing the pH of the solutions, it is possible to shift the aggregation pattern of these nanoparticles, such as the size of the initially formed aggregates.

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Role of an Amide Bond for Self-Assembly of Surfactants

Cited by 101 publications

References 33 publications

Organic corrosion inhibitors: where are we now? A review. Part II. Passivation and the role of chemical structure of carboxylates

Organic corrosion inhibitors: where are we now? A review. Part II. Passivation and the role of chemical structure of carboxylates

Effect of pH on the Binding of Sodium, Lysine, and Arginine Counterions to l‐Undecyl Leucinate Micelles

Silica Nanoparticles with Proton Donor and Proton Acceptor Groups: Synthesis and Aggregation

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