Adsorption at the liquid-liquid interface in the biphasic rhodium catalyzed hydroformylation of olefins promoted by cyclodextrins: a molecular dynamics study

The Journal of Physical Chemistry. B
Nicolas Sieffert, Georges Wipff

Abstract

Using molecular dynamics (MD) simulations, we investigate the interfacial distribution of partners involved in the phase transfer rhodium catalyzed hydroformylation of olefins promoted by beta-cyclodextrins (beta-CDs). The beta-CDs, the reactant (alkene), product (aldehyde), several rhodium complexes (the catalyst, its precursor, and its alkene adduct) are simulated at the water-"oil" interface, where oil is represented by chloroform or hexane. It is shown that unsubstituted beta-CD and its 6-methylated and 2,6-dimethylated analogues adsorb at the interface, whereas the liposoluble permethylated CD does not. The precursor of the catalyst [RhH(CO)(TPPTS)3]9- (with triphenylphosphine trisulfonated TPPTS3- ligands) sits in water, but the less charged [RhH(CO)(TPPTS)2]6- catalyst and the [RhH(CO)(TPPTS)2(alkene)]6- reaction intermediate are clearly surface active. The TPPTS3- anions also concentrate at the interface, where they adopt an amphiphilic conformation, forming an electrical double layer with their Na+ counterions. Thus, the most important key partners involved in the hydroformylation reaction concentrate at the interface, thereby facilitating the reaction, a process which may be further facilitated upon complexation by CD...Continue Reading

References

Feb 1, 1996·Journal of Molecular Graphics·W HumphreyK Schulten
Aug 5, 1997·Chemical Reviews·Kenneth A. Connors
Oct 16, 2003·International Journal of Pharmaceutics·Dominique DuchêneMonique Seiller

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Citations

Apr 25, 2015·Langmuir : the ACS Journal of Surfaces and Colloids·Jackson Chief Elk, Ilan Benjamin
Sep 11, 2010·Applied Spectroscopy·Cathryn L McFearin, Geraldine L Richmond
Jul 28, 2011·Physical Chemistry Chemical Physics : PCCP·Christine CézardFrançois-Yves Dupradeau

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