The Structure of 2,4;3,5-Dimethylene-D-gluconic Acid<sup>1</sup>

Zief, Morris; Scattergood, Allen

doi:10.1021/ja01201a021

Cited by 8 publications

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“…Outline of syntheses of gluconamide derivatives from gluconolactone. Reagents and conditions: i, trioxane, H 2 O-H + ; 6 ii, H + -MeOH; 7 iii, excess alkylamine; 1 iv, TsCl in pyridine, 0 °C; v, imidazole, CHCl 3 , 15 kbar, 50 °C; vi, 4-hydroxypyridine, triethylamine, 115 °C; vii, picolinoyl chloride, CHCl 3 , 0 °C; viii, benzoyl chloride, pyridine, 0 °C; ix, C 6 H 11 C(O)Cl, 0 °C. to electron microscopy grids.…”

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confidence: 99%

Organogel formation and molecular imprinting by functionalized gluconamides and their metal complexes

Hafkamp¹,

Kokke²,

Danke³

et al. 1997

Chem. Commun.

166

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mentioning

confidence: 99%

Organogel formation and molecular imprinting by functionalized gluconamides and their metal complexes

Hafkamp¹,

Kokke²,

Danke³

et al. 1997

Chem. Commun.

166

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“…2,4;3,5-Dimethylene- N - n -octyl - d - gluconamide (8). 2,4;3,5-Dimethylene- d -gluconic acid (20.0 g, 85.4 mmol) was dissolved in 150 mL (10.7 equiv) of octylamine and stirred in a nitrogen atmosphere at 95 °C for 2 days. The solution was diluted with ethyl acetate, and after one night in the refrigerator, a white precipitate was formed which was filtered and additionally washed with n -hexane.…”

Section: Methodsmentioning

confidence: 99%

Organogels from Carbohydrate Amphiphiles

1999

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Gluconamides can be easily functionalized to give a variety of compounds that form organogels with a high viscosity. N-n-octyl-D-gluconamide-6-benzoate gelates a large variety of organic solvents, including 1,2-xylene, chloroform, ethyl acetate, and ethanol, to form gels which are, in some cases, stable even above the boiling point of the pure solvent. The 2-methoxy, 6-imidazolyl, 6-acetyl, and 6-cyclohexanoyl derivatives also show gelation, but the 2,4;3,5-dimethylene-protected derivatives do not. Detailed 1 H NMR, IR, and X-ray powder diffraction studies reveal that the molecules of most gelators are packed in a head-to-tail fashion. If there is, however, the possibility to form interlayer hydrogen bonds, as in the case of N-n-octyl-D-gluconamide or N-n-octyl-D-gluconamide-6-(3pyridyl carboxylate), the molecules are packed head-to-head. Some gluconamides, e.g., those with aliphatic substituents, express their molecular chirality in the supramolecular structures, whereas others, in particular those containing a large aromatic substituent on carbon atom C 6 , yield nonchiral aggregates, probably due to interfering π-π stacking interactions of the substituents. DSC experiments show that the formation of the gels is an entropy-driven process.

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Einstellbare supramolekulare Strukturen eines Gluconamids mit einer Imidazolgruppe

Hafkamp¹,

Feiters²,

Nolte³

1994

Angewandte Chemie

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The Structure of 2,4;3,5-Dimethylene-D-gluconic Acid¹

Abstract: This article confirms the finding of Mehltretter and his collaborators2 that the oxidation of 2,4 ;3,-5-dimethylene-D-gluconic acid with alkaline po-

Cited by 8 publications

References 1 publication

Organogel formation and molecular imprinting by functionalized gluconamides and their metal complexes

Organogel formation and molecular imprinting by functionalized gluconamides and their metal complexes

Organogels from Carbohydrate Amphiphiles

Einstellbare supramolekulare Strukturen eines Gluconamids mit einer Imidazolgruppe

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The Structure of 2,4;3,5-Dimethylene-D-gluconic Acid1

Abstract: This article confirms the finding of Mehltretter and his collaborators2 that the oxidation of 2,4 ;3,-5-dimethylene-D-gluconic acid with alkaline po-

Cited by 8 publications

References 1 publication

Organogel formation and molecular imprinting by functionalized gluconamides and their metal complexes

Organogel formation and molecular imprinting by functionalized gluconamides and their metal complexes

Organogels from Carbohydrate Amphiphiles

Einstellbare supramolekulare Strukturen eines Gluconamids mit einer Imidazolgruppe

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The Structure of 2,4;3,5-Dimethylene-D-gluconic Acid¹