L-ascorbic and D-isoascorbic acids are epimers and their alkanoyl-esters are surfactant-like in water. These ascorbic acid derivatives retain the same stereogenic configurations of the parent molecules. That circumstance strongly affects their physico-chemical properties, both in the solid and in the dispersed states. The thermal behavior of 6-O-L-ascorbyl-dodecanoate (L-ASC12), of 6-O-D-isoascorbyl-dodecanoate (D-ASC12) and of their mixtures was investigated through DSC, XRD and FTIR experiments. The results indicate that the mixtures of the two epimers produce two eutectics and a 1:1 molecular compound, both in the pure phase and in the coagel state. From the phase diagram data, the activity coefficients of the different species and the main excess thermodynamic functions can be calculated. The results provide insight into the effects of stereochemistry on their intermolecular interactions.

Effect of Headgroup Chirality in Nanoassemblies. 2. Thermal Behavior of Vitamin C-Based Surfactants / LO NOSTRO, Pierandrea; Ambrosi, Moira; Ninham, B.; Baglioni, Piero. - In: JOURNAL OF PHYSICAL CHEMISTRY. B, CONDENSED MATTER, MATERIALS, SURFACES, INTERFACES & BIOPHYSICAL. - ISSN 1520-6106. - STAMPA. - 113:(2009), pp. 8324-8331. [10.1021/jp9008288]

Effect of Headgroup Chirality in Nanoassemblies. 2. Thermal Behavior of Vitamin C-Based Surfactants

LO NOSTRO, PIERANDREA;AMBROSI, MOIRA;BAGLIONI, PIERO
2009

Abstract

L-ascorbic and D-isoascorbic acids are epimers and their alkanoyl-esters are surfactant-like in water. These ascorbic acid derivatives retain the same stereogenic configurations of the parent molecules. That circumstance strongly affects their physico-chemical properties, both in the solid and in the dispersed states. The thermal behavior of 6-O-L-ascorbyl-dodecanoate (L-ASC12), of 6-O-D-isoascorbyl-dodecanoate (D-ASC12) and of their mixtures was investigated through DSC, XRD and FTIR experiments. The results indicate that the mixtures of the two epimers produce two eutectics and a 1:1 molecular compound, both in the pure phase and in the coagel state. From the phase diagram data, the activity coefficients of the different species and the main excess thermodynamic functions can be calculated. The results provide insight into the effects of stereochemistry on their intermolecular interactions.
113
8324
8331
LO NOSTRO, Pierandrea; Ambrosi, Moira; Ninham, B.; Baglioni, Piero
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Utilizza questo identificativo per citare o creare un link a questo documento: https://hdl.handle.net/2158/359013
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