Metal extraction by silyl-substituted diphosphonic acids. III. Ester group substituent effects on phosphoryl oxygen basicity

Solvent Extraction and Ion Exchange

Volumn 21, Issue 3, 2003, Pages 331-345

  Zalupski, P R ^a   McAlister, D R ^a   Stepinski, D C ^a   Herlinger, A W ^a  

^a LOYOLA UNIVERSITY CHICAGO   (United States)

Author keywords

Diphosphonic acids; Ester substituent; Ligand basicity; Silyl substituted

Indexed keywords

ALKALINITY; ESTERS; FOURIER TRANSFORM INFRARED SPECTROSCOPY; HYDROGEN BONDS; SOLUBILITY; SUBSTITUTION REACTIONS;

LIGANDS;

SOLVENT EXTRACTION;

ACID; ESTER; METAL EXTRACTION;

EID: 0037670803     PISSN: 07366299     EISSN: None     Source Type: Journal    
DOI: 10.1081/SEI-120020214     Document Type: Article

References (17)

1. Nash, K.L.; Horwitz, E.P. Stability constants for europium (III) complexes with substituted methane diphosphonic acids in acid solutions. Inorg. Chim. Acta 1990, 169, 245-252.
2. Nash, K.L. Thermodynamics of formation of complexes between thorium (IV) and substituted methane diphosphonic acids in acidic solutions. Radiochim. Acta 1991, 54, 171-179.
3. Rizkalla, E.N. Metal chelates of phosphonate-containing ligands. Rev. Inorg. Chem. 1983, 5, 223-304.
4. McAlister, D.R.; Dietz, M.L.; Chiarizia, R.; Zalupski, P.R.; Herlinger, A.W. Metal ion extraction by silyl-substituted diphosphonic acids. Part 2. Effect of alkylene bridge length on aggregation and metal ion extraction behavior. Sep. Sci. Technol. 2002, 37, 2289-2315.
5. McAlister, D.R.; Dietz, M.L.; Chiarizia, R.; Herlinger, A.W. Metal ion extraction by silyl-substituted diphosphonic acids. Part 1. P,P′-di-[3-(trimethylsilyl)-1-propylene] methylene- and ethylenediphosphonic acids. Sep. Sci. Technol. 2001, 36, 3541-3562.
6. Barrans, R.E., Jr.; McAlister, D.R.; Herlinger, A.W.; Chiarizia, R.; Ferraro, J.R. Hydrogen bonding in aggregates of dialkyl-substituted diphosphonic acids and monofunctional analogues. Solvent Extr. Ion Exch. 1999, 17, 1195-1217.
7. Chiarizia, R.; Barrans, R.E., Jr.; Ferraro, J.R.; Herlinger, A.W.; McAlister, D.R. Aggregation of dialkyl-substituted diphosphonic acids and its effect on metal ion extraction. Separation Sci. Technol. 2001, 36, 687-708.
8. Stepinski, D.C.; Nelson, D.W.; Zalupski, P.R.; Herlinger, A.W. Facile high yielding synthesis of symmetric esters of methylenebisphosphonic acid. Tetrahedron 2001, 57, 8637-8645.
9. Vepsalainen, J.J.; Kivikoski, J.; Ahlgren, M.; Nupponen, H.E.; Pohjala, E.K. An improved synthetic method and the first crystal structures for (dihalomethylene) bisphosphonate partial esters. Tetrahedron 1995, 51, 6805-6818.
10. Chiarizia, R.; Horwitz, E.P.; Rickert, P.G.; Herlinger, A.W. Metal extraction by alkyl-substituted diphosphonic acids. Part 1. P,P′-di(2-ethylhexyl) methanediphosphonic acid. Solvent Extr. Ion Exch. 1996, 14, 773-792.
11. Thomas, L.C. The identification of functional groups in organophosphorus compounds. In Analysis of Organic Materials, An International Series of Monographs; Belcher, R., Anderson, D.M.W., Eds.; Academic Press: London, UK, 1974; Vol. 7, 23-46.
12. Exner, O. The inductive effect: theory and quantitative assessment. J. Phys. Org. Chem. 1999, 12, 265-274.
13. Charton, M.; Charton, B.I. The mode of transmission of electrical effects. J. Chem. Soc., Perkin Trans. 2 1999, 2203-2211.
14. Galkin, V.I. Inductive substituent effects. J. Phys. Org. Chem. 1999, 12, 283-288.
15. Bianchi, G.; Howarth, O.W.; Samuel, C.J.; Vlahov, G. Long-range σ-inductive interactions through saturated C-C bonds in polymethylene chains. J. Chem. Soc., Perkin Trans. 2 1995, 1427-1432.
16. 29Si NMR. J. Chem. Soc., Perkin Trans. 2 2000, 545-549.
17. Schlosser, M. Parametrization of substituents: effects of fluorine and other heteroatoms on OH, NH, and CH acidities. Angew. Chem. Int. Ed. 1998, 110, 1496-1513.