Complexation of phosphine ligands with peracetylated β-cyclodextrin in supercritical carbon dioxide: spectroscopic determination of equilibrium constants

Giuseppe Filardo, Onofrio Scialdone, Alessandro Galia, Sebastien Tilloy, Eric Monflier, Michel Ferreira, Edward Charles Navarre

Risultato della ricerca: Article

27 Citazioni (Scopus)

Abstract

The interaction between peracetylated beta-cyclodextrin and several triphenyl phosphine derivatives was studied in supercritical carbon dioxide (scCO2) by UV-visible spectroscopy. The equilibrium constant for a 1:1 complexation reaction was obtained from titration spectra and calculated using two established mathematical models. The values of the equilibrium constants are 1-3 orders of magnitude smaller than those obtained inaqueous solution with analogous phosphines. This is likely due to the absence in scCO2 of the hydrophobic effect, which is replaced by a corresponding, but weaker, CO2-phobic effect. The largest value of Kf wasfound for complexes of diphenyl(4-adamantylphenyl)phosphine, which is rationalized on the basis of theexcellent fit of the phosphine in the cyclodextrin cavity, leading to enhanced host-guest van der Waals interactions. This study can be considered the first step toward the comprehension of the complexationthermodynamics of modified cyclodextrins soluble in scCO2.
Lingua originaleEnglish
pagine (da-a)2573-2578
RivistaDefault journal
Volume111
Stato di pubblicazionePublished - 2007

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phosphine
Equilibrium constants
Complexation
Carbon Dioxide
Cyclodextrins
Ligands
Phosphines
Titration
Spectroscopy
Mathematical models
Derivatives
betadex

All Science Journal Classification (ASJC) codes

  • Physical and Theoretical Chemistry
  • Surfaces, Coatings and Films
  • Materials Chemistry

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Complexation of phosphine ligands with peracetylated β-cyclodextrin in supercritical carbon dioxide: spectroscopic determination of equilibrium constants. / Filardo, Giuseppe; Scialdone, Onofrio; Galia, Alessandro; Tilloy, Sebastien; Monflier, Eric; Ferreira, Michel; Navarre, Edward Charles.

In: Default journal, Vol. 111, 2007, pag. 2573-2578.

Risultato della ricerca: Article

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T1 - Complexation of phosphine ligands with peracetylated β-cyclodextrin in supercritical carbon dioxide: spectroscopic determination of equilibrium constants

AU - Filardo, Giuseppe

AU - Scialdone, Onofrio

AU - Galia, Alessandro

AU - Tilloy, Sebastien

AU - Monflier, Eric

AU - Ferreira, Michel

AU - Navarre, Edward Charles

PY - 2007

Y1 - 2007

N2 - The interaction between peracetylated beta-cyclodextrin and several triphenyl phosphine derivatives was studied in supercritical carbon dioxide (scCO2) by UV-visible spectroscopy. The equilibrium constant for a 1:1 complexation reaction was obtained from titration spectra and calculated using two established mathematical models. The values of the equilibrium constants are 1-3 orders of magnitude smaller than those obtained inaqueous solution with analogous phosphines. This is likely due to the absence in scCO2 of the hydrophobic effect, which is replaced by a corresponding, but weaker, CO2-phobic effect. The largest value of Kf wasfound for complexes of diphenyl(4-adamantylphenyl)phosphine, which is rationalized on the basis of theexcellent fit of the phosphine in the cyclodextrin cavity, leading to enhanced host-guest van der Waals interactions. This study can be considered the first step toward the comprehension of the complexationthermodynamics of modified cyclodextrins soluble in scCO2.

AB - The interaction between peracetylated beta-cyclodextrin and several triphenyl phosphine derivatives was studied in supercritical carbon dioxide (scCO2) by UV-visible spectroscopy. The equilibrium constant for a 1:1 complexation reaction was obtained from titration spectra and calculated using two established mathematical models. The values of the equilibrium constants are 1-3 orders of magnitude smaller than those obtained inaqueous solution with analogous phosphines. This is likely due to the absence in scCO2 of the hydrophobic effect, which is replaced by a corresponding, but weaker, CO2-phobic effect. The largest value of Kf wasfound for complexes of diphenyl(4-adamantylphenyl)phosphine, which is rationalized on the basis of theexcellent fit of the phosphine in the cyclodextrin cavity, leading to enhanced host-guest van der Waals interactions. This study can be considered the first step toward the comprehension of the complexationthermodynamics of modified cyclodextrins soluble in scCO2.

UR - http://hdl.handle.net/10447/7927

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