Monolayer properties of uronic acid bicatenary derivatives at the air–water interface: effect of hydroxyl group stereochemistry evidenced by experimental and computational approaches

Literature Information

Publication Date 2011-07-22
DOI 10.1039/C1CP21365B
Impact Factor 3.676
Authors

Hary Razafindralambo, Aurore Richel, Bernard Wathelet, Christophe Blecker, Jean-Paul Wathelet, Robert Brasseur, Laurence Lins, Jose Miñones, Jr., Michel Paquot


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Abstract

By screening uronic acid-based surfactant interfacial properties, the effect of the hydroxyl group stereochemistry (OH-4) on the conformation of bicatenary (disubstituted) derivatives at the air–water interface has been evidenced by experimental and computational approaches. Physical and optical properties of a monolayer characterized by Langmuir film balance, Brewster angle microscopy, and ellipsometry at 20 °C reveal that the derivative of glucuronate (C14/14–GlcA) forms a more expanded monolayer, and shows a transition state under compression, in the opposite to that of galacturonate (C14/14–GalA). Both films are very mechanically resistant (compression modulus > 300 mN m−1) and stable (collapse pressure exceeding 60 mN m−1), while that of C14/14–GalA exhibits a very high compression modulus up to 600 mN m−1 like films in the solid state. Computational approaches provide single and assembly molecular models that corroborate the molecule expansion degree and interactions data from experimental results. Differences in the molecular conformation and film behaviours of uronic acid bicatenary derivatives at the air–water interface are attributed to the intra-H-bonding formation, which is more favourable with an OH-4 in the axial (C14/14–GalA) than in the equatorial position (C14/14–GlcA).

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