Molecular and crystal structures of N-(n-heptyl)- and N-(n-decyl)-d-gluconamide

Mueller‐Fahrnow, Anke; Hilgenfeld, Rolf; Hesse, H.; Pfannemueller, B.

doi:10.1016/0008-6215(88)80128-9

Cited by 40 publications

(9 citation statements)

References 6 publications

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“…The properties of analogous single-chain, single-head, sugar-based surfactants have been investigated previously. − In some cases, unusual behavior is observed, such as gel formation at low concentrations or insolubility; however, such problems do not arise with most of the new glucamide surfactants described here.…”

Section: Introductionmentioning

confidence: 90%

Properties of New Glucamide Surfactants

Eastoe¹,

Rogueda²,

Howe³

et al. 1996

Langmuir

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Properties of new nonionic surfactants are reported. The amphiphiles possess two n-alkyl chains and two glucamide head-groups and have the formula (C n H2n+1)2C[CH2NHCO(CHOH)4CH2OH]2 with n = 5−9 (abbreviated here as di-(Cn-Glu)). For di-(C7-Glu) in the concentration range 0.4−8%, an upper critical solution temperature (UCST) is observed; this is unusual behavior for a nonionic surfactant. Nonetheless these materials behave like classic surfactants with regard to changes in liquid crystal phases, surface tensions, and critical micelle concentrations (cmc's) as a function of chain length n. Small-angle neutron scattering (SANS) data indicate the presence of anisotropic micelles, cylindrical for di-(C5-, 6-, and 7-Glu) but discoidal for di-(C8-Glu). There is apparently little effect of temperature (25−70 °C) on cmc or micelle structures.

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Section: Introductionmentioning

confidence: 90%

Properties of New Glucamide Surfactants

Eastoe¹,

Rogueda²,

Howe³

et al. 1996

Langmuir

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“…van Doren (5) reported his work on N-acyl-N-alkyl-1-amino-1-deoxy-D-glucitols (number of carbon atoms in the acyl group: n = 0-5) and constructed a model based on the relationship between the total number of hydroxyl/ carbonyl groups, the total number of carbon atoms in the acyl and alkyl chain, and the lyotropic mesophase for predicting behavior of these compounds such as Krafft temperature, critical micelle concentration (CMC), and toxicity. Other work investigated their solid and liquid crystal structures and gel formation in aqueous solution (6)(7)(8)(9). However, that work both on glucosides and on glucamides focused on surfactants with only octyl or decyl groups as hydrophobic moieties.…”

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confidence: 99%

Surface properties of N‐alkanoyl‐N‐methyl glucamines and related materials

Zhu

Rosen

Vinson

et al. 1999

J Surfact & Detergents

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The surface properties [effectiveness of surface tension reduction (γ CMC ), critical micelle concentration (CMC), efficiency of surface tension reduction (pC 20 ), maximal surface excess concentration (Γ max ), minimal area/molecule at the interface (A min ), and the (CMC/C 20 ) ratio] of some well-purified N-alkanoyl-N-methyl glucamines and related polyol-based Nmethyl amide-type surfactants, having the structural formula RC(O)N(Me)CH 2 (CHOH) x CH 2 OH, where RC(O) = undecanoyl, lauroyl, tridecanoyl, myristoyl, and x = 1, 3, and 4, were investigated at 25°C in distilled water and 0.1 M NaCl. Water solubility of these compounds does not simply depend on the number of hydroxyl groups in the molecule but is associated with the balance between intermolecular hydrogen bonds and hydrogen bonds formed with water molecules. The fundamental interfacial properties, such as CMC and γ CMC , and two thermodynamic parameters, standard free energy of adsorption and standard free energy of micellization, were found to be significantly dependent on the hydrophobic acyl chain rather than on the number of CHOH groups in the hydrophilic moieties. By contrast, the practical performance properties were greatly dependent on the nature of the hydrophilic group. As a whole, these surfactants had desirable foaming properties and efficient wetting abilities. Furthermore, synergism in foaming and wetting abilities was observed in a binary mixture of these surfactants with an alkyloxyethylene sulfate.

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“…However in the coplanar conformation there is sterical strain due to the hydrogens at C6, C8, Cll and C15. While in the vapor phase and in the liquid phase the two phenyl rings in biphenyl are twisted by 44 other, respectively, in czystals the twist angle depends upon packing requirements which can be modified by substituents at positions adjacent to the C7-C10 bond.…”

Section: Resultsmentioning

confidence: 99%

“…In contrast to amineoxides, carbohydrates have both hydrogen bonding donors and acceptors. Crystals of carbohydrate amphiphiles thus tend to exclude water molecules [38][39][40][41][42][43][44][45][46][47]. The lack of suitable hydrogen bonding donors in amineoxide compounds explains the requirement for the inclusion of water molecules into their crystalline lattice.…”

Section: Resultsmentioning

confidence: 99%

Molecular and crystal structure of an amphiphile: 4′-propoxybiphenyl-4-methyl-N,N-dimethylamineoxide dihydrate

Diederichs

Welte

Hauk

et al. 1995

Biochimica et Biophysica Acta (BBA) - Biomembranes

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A novel amphiphile, 4'-propoxybiphenyl-4-methyl-N,N-dimethylamineoxide, has been synthesized, crystallized (P2(1)/a, a = 9.084 A, b = 8.911 A, c = 22.460 A, beta = 96.224 degrees) and its crystal structure was determined. The amphiphile forms a bilayer in which the amineoxide oxygen of each molecule binds two water molecules. In the hydrophobic part of the bilayer the biphenyls form edge-to-face contacts, in the polar layer there is a hydrogen bonding network. The potential use of the compound as a detergent for membrane proteins has been demonstrated and the relevance of the amineoxide hydrate for other detergents discussed.

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Molecular and crystal structures of N-(n-heptyl)- and N-(n-decyl)-d-gluconamide

Cited by 40 publications

References 6 publications

Properties of New Glucamide Surfactants

Properties of New Glucamide Surfactants

Surface properties of N‐alkanoyl‐N‐methyl glucamines and related materials

Molecular and crystal structure of an amphiphile: 4′-propoxybiphenyl-4-methyl-N,N-dimethylamineoxide dihydrate

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