NMR Spectroscopy and the Effects of Enantiomerism on the Micelle Formation of PotassiumN-n-Dodecanoylalaninate

Desando, M. A.; McGarvey, Bruce R.; Reeves, L. W.

doi:10.1006/jcis.1996.0386

Cited by 12 publications

(6 citation statements)

References 12 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…Miyagishi et al reported similar results and explained the difference in cmc in terms of the difference of the conformation of aminoacid part in the surfactant molecule on the micellar surface (17). However, Desando et al have recently reported identical cmc values for optically active (D-and L-) and racemic (DL-) system of potassium N-dodecanoyl alaninate (18). We are not aware of any study of the aggregation behavior of optically-active and racemate systems on aqueous N-acylaminoacid surfactants at higher surfactant concentrations.…”

Section: Dp Acharya Ma Lopez-quintela H Kunieda Et Almentioning

confidence: 83%

Phase Behavior and Effect of Enantiomerism on Potassium N -Dodecanoyl Alaninate/Water/Decanol Systems

Acharya¹,

López‐Quintela²,

Kunieda³

et al. 2003

J. Oleo Sci.

View full text Add to dashboard Cite

Section: Dp Acharya Ma Lopez-quintela H Kunieda Et Almentioning

confidence: 83%

Phase Behavior and Effect of Enantiomerism on Potassium N -Dodecanoyl Alaninate/Water/Decanol Systems

Acharya¹,

López‐Quintela²,

Kunieda³

et al. 2003

J. Oleo Sci.

View full text Add to dashboard Cite

“…It is interesting to note a lack of any significant dependency of ∆δ on electrolyte concentration and hence on the size of the aggregate. From the inspection of Figures 7 and 8 we deduce that the greatest change of chemical shift is with the proton at the polar head rather than in the middle of the alkyl chain as reported for the micellization of sodium hexanoate, sodium octanoate, nonylammonium bromide, and potassium N-n-dodecanonyl-D-alaninate, 28,29 suggesting differences in aggregate structure for sodium n-hexyl sulfate. where m m and m are the concentration of aggregated surfactant and the total surfactant concentration, respectively.…”

Section: Experimental Data Have Been Fitted With the Linear Functionmentioning

confidence: 84%

Light Scattering and NMR Studies on the Self-Aggregation of Sodium n-Hexyl Sulfate in Aqueous Electrolyte Solution

et al. 1999

View full text Add to dashboard Cite

The self-aggregation of sodium n-hexyl sulfate (SHS) in aqueous solution has been studied from static and dynamic light scattering and 1 H nuclear magnetic resonance (NMR) at 25°C in the presence of added electrolyte concentration (0.0-0.5 mol kg -1 NaCl). Critical concentrations, aggregation numbers, effective aggregate charges, and degrees of aggregate ionization have been calculated, with similar results from each of the different techniques. The interaction between aggregates was interpreted from diffusion data from dynamic light scattering using DLVO theory. Aggregation properties have been determined by application of mass action theory to the concentration dependence of 1 H NMR chemical shifts, confirming the results obtained by the light scattering techniques.

show abstract

mentioning

confidence: 99%

“…However, there are only a few studies of the relationship between the surface properties, such as critical micelle concentration (CMC), efficiency of surface tension reduction (pC 20 ), and area per molecule of N-acylated amino acid surfactants, and their chemical structure. As far as we know, studies have been limited to the derivatives of sarcosine (7), alanine, glycine (8,9) and glutamic acid (10,11) and have focused on the effect of the straight alkyl chain on the CMC and the conformational behavior in their aqueous micellar solutions (12)(13)(14)(15).In this study, a new type of highly purified N-substituted-N-acyl amino acids (Scheme 1), in which various short side alkyl chains R′ are attached to the peptide nitrogen atom between a long straight alkyl chain R of the acyl group and the main hydrophilic carboxylate group was examined in detail. The effect of structure on surface properties of this amino acid salt series was studied by varying the structure of both the main chain R and the side chain R′.…”

mentioning

confidence: 99%

Chemical structure/property relationships in surfactants. 17. N‐substituted‐N‐acyl glycinates in pure and synthetic hard river water

Zhu

Rosen

Morrall

1998

J Surfact & Detergents

View full text Add to dashboard Cite

The surface properties [effectiveness of surface tension reduction (γ CMC ), critical micelle concentration (CMC), efficiency of surface tension reduction (pC 20 ), maximum surface excess concentration (Γ max ), minimum area/molecule at the interface (A min ), and the CMC/C 20 ) ratio] of well-purified N-substituted glycine derivatives, having the structural formula RC(O)N(R′)CH 2 COONa, where RC(O) = lauroyl, myristoyl, or oleoyl, and R′ = Et, Pr, Bu, CH 2 CH 2 OH or CH 2 CH 2 CH 2 OCH 3 , were investigated at 25°C in hard river water and distilled water. These surfactants show greater surface activity in hard river water than in distilled water. The effect of both the main alkyl chain R and the N-substituent R′ on surface properties was elucidated, the oleoyl group showing properties equivalent to that of a C 16 saturated acyl group. A linear relationship was observed between the pC 20 or CMC values and the number of carbon atoms in the alkyl chain R or in R′ when it was alkyl. With increase in the number of carbon atoms in either R or the N-substituent R′ when it is alkyl, both pC 20 and micelle-forming ability increase, although the effect of R′ on the foregoing two surface properties is lower than that of R. When R′ is (CH 2 ) 3 OCH 3 , however, the results suggest that R′ is only partly removed from contact with the aqueous phase either upon adsorption at the water/air interface or upon micellization. It increases A min , is equivalent only to an ethyl group in its effect on pC 20 and to a methyl group in its effect on CMC, and, in contrast to the effect of R′ when it is alkyl, produces no increase in the CMC/C 20 ratio. As a result, γ CMC increases with R when R′ is alkyl and decreases with R when R′ is (CH 2 ) 3 OCH 3 . JSD 1, 1-9 (1998).Among the anionic surfactants, N-acylated amino acidtype surfactants have unique properties, showing some advantages over other types of anionic surfactants, that is, high biodegradability in the environment, compatibility with cationic surfactants, more tolerance of water hardness than the similar carboxylate-type surfactants, and low irritation to skin. These unique properties have made them desirable in products as diverse as shampoos, toothpaste, hand cleaners, pharmaceuticals, antimicrobial agents, ore flotation agents, and corrosion inhibitors (1-4). Also, because amino acid surfactants are generally considered as models of naturally occurring biosurfactants such as proteins and lipids, the study of their surface properties is of great importance in understanding their roles in biological systems. In fact, there are at least two reports concerning this aspect: the surface molecular recognition of amino acid (5) and the formation of fibrous molecular assemblies by amino acid surfactants in an aqueous medium (6). However, there are only a few studies of the relationship between the surface properties, such as critical micelle concentration (CMC), efficiency of surface tension reduction (pC 20 ), and area per molecule of N-acylated amino acid surfactants, and their che...

show abstract

NMR Spectroscopy and the Effects of Enantiomerism on the Micelle Formation of PotassiumN-n-Dodecanoylalaninate

Cited by 12 publications

References 12 publications

Phase Behavior and Effect of Enantiomerism on Potassium N -Dodecanoyl Alaninate/Water/Decanol Systems

Phase Behavior and Effect of Enantiomerism on Potassium N -Dodecanoyl Alaninate/Water/Decanol Systems

Light Scattering and NMR Studies on the Self-Aggregation of Sodium n-Hexyl Sulfate in Aqueous Electrolyte Solution

Chemical structure/property relationships in surfactants. 17. N‐substituted‐N‐acyl glycinates in pure and synthetic hard river water

Contact Info

Product

Resources

About