Supramolecular Interactions of Cryptates in Concentrated Solutions: The Effect of Solvent and Counterions Investigated by MD Simulations

References

• Dietrich , B. , Lehn , J. M. and Sauvage , J. P. 1973 . Complexes macrobicycliques, formation, structure, propriétés . Tetrahedron , 29 : 1647 – 1658 .
   Web of Science ®Google Scholar
• Lehn , J. M. 1973 . Design of organic complexing agents. Strategies towards properties . Struct. Bonding , 161 : 1 – 69 .
   Google Scholar
• Kauffmann , E. , Lehn , J. M. and Sauvage , J. P. 1976 . Enthalpy and entropy of formation of alkali and alkali-earth macrobicyclic cryptate complexes . Helv. Chim. Acta. , 59 : 1099 – 1111 .
   Web of Science ®Google Scholar
• Calixarenes . 2001 . Dordrecht : Kluwer Academic Publisher . 2001
   Google Scholar
• Gokel , G. 1991 . Crown Ethers and Cryptands Miami : Royal Society of Chemistry .
   Google Scholar
• Izatt , R. M. , Pawlak , K. and Bradshaw , J. S. 1991 . Thermodynamic and kinetic data for macrocycle interaction with cations and anions . Chem. Rev. , 91 : 1721 – 2085 .
   Web of Science ®Google Scholar
• Inoue , Y. and Gokel , G. 1990 . Cation Binding by Macrocycles. Complexation of Cationic Species by Crown Ethers New York and Basel : M. Dekker, Inc. .
   Google Scholar
• Gloe , K. 2005 . Macrocyclic Chemistry. Current Trends and Future Perspectives Springer .
   Google Scholar
• Behr , J. P. , Kirch , M. and Lehn , J.‐M. 1985 . Carrier-mediated transport through bulk liquid membranes: Dependence of transport rates and selectivity on carrier properties in a diffusion-limited process . J. Am. Chem. Soc. , 107 : 241 – 246 .
   Web of Science ®Google Scholar
• Lamb , J. D. , Christensen , J. J. , Oscarson , J. L. , Nielsen , B. L. , Asay , B. W. and Izatt , R. M. 1980 . The relationship between complex stability constants and rates of cation transport through liquid membranes by macrocyclic carriers . J. Am. Chem. Soc. , 102 : 6820 – 6824 .
   Web of Science ®Google Scholar
• Watarai , H. 1993 . What's happening at the liquid-liquid interface in solvent extraction chemistry? . Trends in Analytical Chemistry , 12 : 313 – 318 .
   Web of Science ®Google Scholar
• Szymanowski , J. 2000 . Kinetics and interfacial phenomena . Solv. Extract. Ion Exch. , 18 : 729 – 751 .
   Web of Science ®Google Scholar
• Berny , F. , Muzet , N. , Troxler , L. and Wipff , G. 1999 . Supramolecular Science: Where it is and where it is Going Edited by: Ungaro , R. and Dalcanale , E. 95 – 125 . Dordrecht : Kluwer Acad. Pub. . and references cited therein
   Google Scholar
• Schurhammer , R. , Berny , F. and Wipff , G. 2001 . Importance of interfacial phenomena in assisted ion extraction by supercritical CO2: a molecular dynamics investigation . Phys. Chem. Chem. Phys. , 3 : 647 – 656 .
   Web of Science ®Google Scholar
• Baaden , M. , Berny , F. and Wipff , G. 2001 . The chloroform/TBP/aqueous nitric acid interfacial system: a molecular dynamics investigation . J. Mol. Liquids , 90 : 3 – 12 .
   Web of Science ®Google Scholar
• Guilbaud , P. and Wipff , G. 1996 . MD simulations on UO2 2+ and Sr2+ complexes with CMPO derivatives in aqueous solution and at a water/chloroform interface . New J. Chem. , 20 : 631 – 642 .
   Web of Science ®Google Scholar
• Lauterbach , M. and Wipff , G. 1996 . Physical Supramolecular Chemistry Edited by: Echegoyen , L. and Kaifer , A. 65 – 102 . Dordrecht : Kluwer Acad. Pub. .
   Google Scholar
• Troxler , L. and Wipff , G. 1998 . Interfacial behaviour of ionophoric systems: Molecular dynamics studies on 18-crown-6 and its complexes at the water—chloroform interface . Anal. Sciences , 14 : 43 – 56 .
   Web of Science ®Google Scholar
• Jost , P. , Galand , N. , Schurhammer , R. and Wipff , G. 2002 . 222 cryptand and its cryptates at the water/chloroform interface: molecular dynamics investigations of concentrated solutions . Phys. Chem. Chem. Phys. , 4 : 335 – 344 .
   Web of Science ®Google Scholar
• Lauterbach , M. , Engler , E. , Muzet , N. , Troxler , L. and Wipff , G. 1998 . Migration of ionophores and salts through a water- chloroform liquid-liquid interface: Computer MD-PMF investigations . J. Phys. Chem. B , 102 : 225 – 256 .
   Web of Science ®Google Scholar
• Vrbka , L. , Mucha , M. , Minofar , B. , Jungwirth , P. , Brown , E. C. and Tobias , D. J. 2004 . Propensity of soft ions for the air/water interface . Curr. Op. Coll. Interf. Sc. , 9 : 67 – 73 .
   Web of Science ®Google Scholar
• Kunz , W. , Nostro , P. L. and Ninham , B. W. 2004 . The present state of affairs with Hofmeister effects . Curr. Op. Coll. Interf. Sc. , 9 : 1 – 18 .
   Web of Science ®Google Scholar
• Marcus , Y. and Kertes , A. S. 1969 . Ion Exchange and Solvent Extraction of Metal Complexes New York : Wiley‐Interscience .
   Google Scholar
• Chiarizia , R. , Jensen , M. P. , Borkowski , M. , Ferraro , J. R. , Thiyagarajan , P. and Littrell , K. C. 2003 . Third phase formation revisited: The U(VI), HNO3-TBP, n-dodecane system . Solv. Extract. Ion Exch. , 21 : 1 – 27 .
   Web of Science ®Google Scholar
• Rao , P. R.V. and Kolarik , Z. 1996 . A review of third phase formation in extraction of actinides by neutral organophosphorus extractants . Solvent Extr. Ion Exch. , 14 : 955 – 993 .
   Web of Science ®Google Scholar
• Cox , B. G. , Garcia‐Rosas , J. and Schneider , H. 1981 . Solvent dependence of the stability of cryptates complexes . J. Am. Chem. Soc. , 103 : 1384 – 1389 .
   Web of Science ®Google Scholar
• Buschmann , H. J. , Wenz , G. and Schollmeyer , E. 2001 . Chloroform as solvent for the complex formation of alkaline salts with crown ethers and cryptands . Inorg. Chem. Commun. , : 53 – 56 .
   Web of Science ®Google Scholar
• Mucha , M. , Frigato , T. , Levering , L. M. , Allen , G. C. , Tobias , D. J. , Dang , L. X. and Jungwirth , P. 2005 . Unified molecular picture of the surface of aqueous acid, base, and salt solutions . J. Phys. Chem. B , 109 : 7617 – 7623 .
   PubMed Web of Science ®Google Scholar
• Berny , F. , Schurhammer , R. and Wipff , G. 2000 . Distribution of hydrophilic, amphiphilic, and hydrophobic ions at a liquid-liquid interface: a molecular dynamics investigation . Inorg. Chim. Acta , 300–302 : 384 – 394 .
   Web of Science ®Google Scholar
• Galand , N. and Wipff , G. 2005 . Potassium extraction by a cryptand to supercritical CO2. The role of counterions investigated by MD simulations at the water/SC-CO2 interface . Supramol. Chem. , 17 : 453 – 464 .
   Web of Science ®Google Scholar
• Cram , D. J. and Ho , S. P. 1986 . Host-guest complexation. 39. Cryptahemisperands are highly selective and strongly binding hosts for alkali metal ions . J. Am. Chem. Soc. , 108 : 2998 – 3005 .
   Web of Science ®Google Scholar
• Cartailler , T. , Calmettes , P. , Kunz , W. , Turq , P. and Rossy‐Delluc , S. 1993 . Cryptates as model brownons. I- Small angle neutron scattering experiments . Mol. Phys. , 80 : 833 – 841 .
   Web of Science ®Google Scholar
• Kunz , W. , Calmette , P. , Turq , P. , Cartailler , T. , Morel‐Desrosiers , N. and Morel , J.‐P. 1992 . Pair correlation functions of uncharged and weakly charged brownian particles . J. Chem. Phys. , 97 : 5647 – 5652 .
   Web of Science ®Google Scholar
• Case , D. A. , Pearlman , D. A. , Caldwell , J. C. , Cheatham , T. E. III , Ross , W. S. , Simmerling , C. L. , Darden , T. A. , Merz , K. M. , Stanton , R. V. , Cheng , A. L. , Vincent , J. J. , Crowley , M. , Ferguson , D. M. , Radmer , R. J. , Seibel , G. L. , Singh , U. C. , Weiner , P. K. and Kollman , P. A. 1997 . AMBER5 San Francisco : AMBER5, University of California .
   Google Scholar
• Auffinger , P. and Wipff , G. 1991 . Hydration of the bicyclic 222 cryptand and 222 cryptates studied by molecular dynamics simulations . J. Am. Chem. Soc. , 113 : 5976 – 5988 .
   Web of Science ®Google Scholar
• Troxler , L. , Harrowfield , J. M. and Wipff , G. 1998 . Do picrate anions “attract each other” in solution? Molecular dynamics simulations in water and in acetonitrile solutions . J. Phys. Chem. A , 102 : 6821 – 6830 .
   Web of Science ®Google Scholar
• Jorgensen , W. L. , Chandrasekhar , J. , Madura , J. D. , Impey , R. W. and Klein , M. L. 1983 . Comparison of simple potential functions for simulating liquid water . J. Chem. Phys. , 79 : 926 – 936 .
   Web of Science ®Google Scholar
• Darden , T. A. , York , D. M. and Pedersen , L. G. 1993 . Particle Mesh Ewald: an N log(N) method for Ewald sums in large systems . J. Chem. Phys. , 98 : 10089
   Web of Science ®Google Scholar
• Tironi , I. G. , Sperb , R. , Smith , P. E. and van Gunsteren , W. F. 1995 . A generalized reaction field method for molecular dynamics simulations . J. Chem. Phys. , 102 : 5451 – 5459 .
   Web of Science ®Google Scholar
• Berendsen , H. J.C. , Postma , J. P.M. , van Gunsteren , W. F. and DiNola , A. 1984 . Molecular dynamics with coupling to an external bath . J. Chem. Phys. , 81 : 3684 – 3690 .
   Web of Science ®Google Scholar
• Engler , E. and Wipff , G. 1996 . Crystallography of Supramolecular Compounds Edited by: Tsoucaris , G. 471 – 476 . Dordrecht : Kluwer .
   Google Scholar
• Dobler , M. 1981 . Ionophores and Their Structures New York : Wiley Interscience .
   Google Scholar
• Srinivasan , V. and Blankschtein , D. 2003 . Effect of counterion binding on micellar solution behavior: 2 Prediction of micellar solution properties of ionic surfactants—electrolytes systems . Langmuir , 19 : 9946 – 9961 .
   Web of Science ®Google Scholar
• Chevrot , G. , Schurhammer , R. and Wipff , G. 2006 . Surfactant behavior of “ellipsoidal” dicarbollide anions. A molecular dynamics study . J. Phys. Chem. B , 110 : 9488 – 9498 .
   PubMed Web of Science ®Google Scholar
• Rais , J. and Grüner , B . 2004 . Ion Exchange and Solvent Extraction Edited by: Marcus , Y. , SenGupta , A. K. and Marinsky , J. A. Vol. 17 , 243 – 334 . New York : M. Dekker . Chap. 5
   Google Scholar
• Popov , A. and Borisova , T. 2001 . Adsorption of CCD− at the water/1,2-dichloro interface. Influence of counterions' nature . J. Colloid Interfaces , 236 : 20 – 27 .
   PubMed Web of Science ®Google Scholar
• Matejicek , P. , Cigler , P. , Prochazka , K. and Kral , V. 2006 . Molecular assembly of metallocarboranes in water: light scattering and microscopic study . Langmuir , 22 : 575 – 589 .
   PubMed Web of Science ®Google Scholar
• Chaumont , A. and Wipff , G. 2002 . Macrotricyclic quaternary tetraammonium receptors: halide anion recognition and interfacial activity at an aqueous interface. A molecular dynamics investigation . J. Comput. Chem. , 23 : 1532 – 1543 .
   PubMed Web of Science ®Google Scholar
• Lambert , B. , Jacques , V. , Shivanyuk , A. , Matthews , S. E. , Tunayar , A. , Baaden , M. , Wipff , G. , Böhmer , V. and Desreux , J.‐F. 2000 . Calix[4]arenes as selective extracting agents. A NMR dynamic and conformational investigation of the Lanthanide(III) and Thorium(IV) complexes . Inorg. Chem. , 39 : 2033 – 2041 .
   PubMed Web of Science ®Google Scholar
• Chiariza , R. , Urban , V. , Thiyagarajan , P. and Herlinger , A. W. 1999 . Aggregation of complexes formed in the extraction of selected cations by P,P′-Di(2-EthylHexyl)methannedisphosphonic acid . Solv. Extract. Ion Exch. , 17 : 113 – 132 .
   Web of Science ®Google Scholar
• Chiarizia , R. , Rickert , P. G. , Stepinski , D. , Thiyagarajan , P. and Littrell , K. C. 2006 . SANS study of third phase formation in the HCI-TBP-n-octane system . Solv. Extract. Ion Exch. , 24 : 125 – 148 .
   Web of Science ®Google Scholar