Cloth-like aggregates of micellar fibers made of N-dodecyltartaric acid monoamides

Fuhrhop, Jürgen‐Hinrich; Demoulin, Corinna; Rosenberg, Jörg; Boettcher, Christoph

doi:10.1021/ja00163a069

Cited by 50 publications

(44 citation statements)

References 2 publications

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“…The lower values of cac and cvc suggest that aggregation is more favored in the cases of SAUAS and SAUGL. It is well known that hydrogenbonding (HB) interaction between the secondary amide groups of adjacent NAA surfactant molecules facilitates aggregate formation [6,[19][20][21][22][23][24][25]. The relatively stronger intermolecular HB interaction between the primary (CONH 2 ) and the secondary (CONH) amide groups of adjacent surfactant molecules might be responsible for lowering the cac of SAUAS and SAUGL compared to that of SAUS.…”

Section: Critical Aggregation Concentrationmentioning

confidence: 99%

“…In fact, the possible driving force for the formation of helical and/or cylindrical aggregates is the interaction between headgroups of the amphiphiles [1][2][3][4][5][6]. Recent studies have shown that short-range attractive interactions such as hydrogen bonding could also be a driving force in the formation of bilayer self-assemblies [7][8][9][10][11][12][13].…”

Section: Introductionmentioning

confidence: 99%

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Effect of hydrogen-bonding interactions on the self-assembly formation of sodium N-(11-acrylamidoundecanoyl)-l-serinate, l-asparaginate, and l-glutaminate in aqueous solution

Roy

Dey

2007

Journal of Colloid and Interface Science

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Section: Critical Aggregation Concentrationmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

Effect of hydrogen-bonding interactions on the self-assembly formation of sodium N-(11-acrylamidoundecanoyl)-l-serinate, l-asparaginate, and l-glutaminate in aqueous solution

Roy

Dey

2007

Journal of Colloid and Interface Science

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“…Since both (S)-Leu-7 and (R)-PhG-7 possess structural characteristics of amphiphiles, intermolecular interactions between lipophilic parts and between highly polar parts would be expected. [29] In the micellar fibres formed by the amphiphilic N-dodecyl-tartaric acid monoamide sodium salt [30] and in the bilayered crystal structure of potassium palmitate [31] electrostatic and iondipole interactions between sodium or potassium carboxylates were found. Hence, for the (S)-Leu-7 and (R)-PhG-7 gel aggregates, the same type of interactions may account for the observed additional stabilization, particularly in toluene, due to its poor ability to solvate ions.…”

Section: Ftir and 1 H Nmr Investigationmentioning

confidence: 99%

Chiral Gelators Constructed from 11‐Aminoundecanoic (AUDA), Lauric and Amino Acid Units. Synthesis, Gelling Properties and Preferred Gelation of Racemates vs. the Pure Enantiomers

et al. 2004

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A new class of efficient low molecular weight gelator molecules has been designed by combining 11‐aminoundecanoic acid (AUDA), lauric acid and aromatic and aliphatic amino acid units in the same molecule. This yields a special class of fatty acid amphiphiles with core chiral centres and hydrogen bonding sites. Some of the compounds with terminal carboxylic acid and sodium carboxylate functions exhibited ambidextrous gelation properties, being able to form gels both with highly polar solvents (water, DMSO) and also with highly lipophilic solvents, including two hydrocarbon fuels. At variance with several recent observations that the enantiomers are generally more efficient gelators than the corresponding racemates, some of the racemic gelators prepared in this work were found to be capable of gelling up to 16 times larger volumes of certain solvents than the pure enantiomers. Temperature‐dependent FTIR and 1H NMR studies of the gels formed by derivatives with terminal carboxylic acid groups and lipophilic solvents revealed that intermolecular hydrogen bonding between amidic and carboxylic acid units was involved in the self‐assembly of gel aggregates. Additional strong stabilization of the aggregates was observed in the gelators possessing terminal sodium carboxylate groups, and this was attributed to the electrostatic and ion‐dipole interactions between the sodium carboxylate groups. This additional stabilization appears to be responsible for considerably higher thermal stability of the latter gels in relation to those formed by gelators with terminal carboxylic acid groups. (© Wiley‐VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2004)

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“…Relevant to our work, should be mentioned work dealing with tartramonoamides reported earlier by Fuhrhop et al These authors reported that enatiomerically pure tartramonoamides formed ultrathin fibers, while racemates appeared as planar platelets. 25,26 …”

Section: Introductionmentioning

confidence: 99%

Investigation of tartaric acid amide formation by thermolysis of tartaric acids with alkylamines

González¹,

Carlsen²

2011

Arkivoc

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N,N′-dialkyltartramides were obtained by conventional thermolysis at 200 o C without a solvent, of the L-, D-or meso-tartaric acids with butyl-, hexyl-and octylamine, respectively. The products proved in all cases to be mixtures of all the possible stereoisomers, in ratios that depended on the stereochemistry of the tartaric acid applied, retaining an excess of the configuration of the starting material. Isomerization of the initially formed diamide did not take place under the reaction conditions. Mechanistically the transformation was rationalized in terms of two competing pathways -the direct substitution of the alkylamine into the carboxylic acid group, -in competition with ketene formation and subsequent amide formation. As a method for stereoselective synthesis of optically active N,N′-dialkyltartramides, the method may be considered obsolete and of little practical value; however, it provided new insight into the mechanisms of amide formation.

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Cloth-like aggregates of micellar fibers made of N-dodecyltartaric acid monoamides

Cited by 50 publications

References 2 publications

Effect of hydrogen-bonding interactions on the self-assembly formation of sodium N-(11-acrylamidoundecanoyl)-l-serinate, l-asparaginate, and l-glutaminate in aqueous solution

Effect of hydrogen-bonding interactions on the self-assembly formation of sodium N-(11-acrylamidoundecanoyl)-l-serinate, l-asparaginate, and l-glutaminate in aqueous solution

Chiral Gelators Constructed from 11‐Aminoundecanoic (AUDA), Lauric and Amino Acid Units. Synthesis, Gelling Properties and Preferred Gelation of Racemates vs. the Pure Enantiomers

Investigation of tartaric acid amide formation by thermolysis of tartaric acids with alkylamines

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