Use of a fluoride ion selective electrode as a tool for monitoring relatively fast kinetic processes. Applications to the hydrolysis of organofluorophosphorus esters and 2,4-dinitrofluorobenzene

Electroanalysis

Volumn 12, Issue 17, 2000, Pages 1403-1407

  Moutiers, Gilles ^a   Le Guével, Eric ^b   Villien, Luc ^b   Terrier, François ^a  

^a UNIVERSITÉ DE VERSAILLES SAINT QUENTIN EN YVELINES   (France)

^b CENTRE D ETUDES DU BOUCHET   (France)

Author keywords

Diisopropylphosphorofluoridate; Fluoride ion selective electrode; Insecticides; Kinetics; Organofluorophosphorus esters; Oximate ion reactivity; Sarin; Soman

Indexed keywords

ESTERS; FLUORINE COMPOUNDS; HYDROLYSIS; ION SELECTIVE ELECTRODES;

DIISOPROPYLPHOSPHOROFLUORIDATE; FAST KINETICS; FLUORIDE ION; FLUORIDE ION SELECTIVE ELECTRODE; ION-SELECTIVE ELECTRODE; KINETIC PROCESS; ORGANOFLUOROPHOSPHORUS ESTER; OXIMATE ION REACTIVITY; SARIN; SOMAN;

IONS;

1 FLUORO 2,4 DINITROBENZENE; 4 CHLOROPHENOL; BUFFER; DYFLOS; FLUORIDE ION; SARIN; SOMAN;

AQUEOUS SOLUTION; ARTICLE; DECOMPOSITION; HYDROLYSIS; ION SELECTIVE ELECTRODE; PH; POTENTIOMETRY; REACTION TIME; TITRIMETRY;

EID: 0033663877     PISSN: 10400397     EISSN: None     Source Type: Journal    
DOI: 10.1002/1521-4109(200011)12:17<1403::AID-ELAN1403>3.0.CO;2-A     Document Type: Article

References (33)

1. Organophosphorus Poisons - Anticholinesterases and Related Compounds (Ed: D.F. Heath), Pergamon Press, New York 1961.
2. a) B. Segues, E. Perez, I. Rico-Lattes, M. Rivier, A. Lattes, Bull. Soc. Chim. Fr. 1996, 133, 925;
3. b) P. Eychenne, I. Rico, E. Perez, A. Lattes, A. New. J. Chem. 1995, 19, 193.
4. a) Y.C. Yang, J.A. Baker, J.R. Ward, Chem. Rev. 1992, 92, 1729;
5. b) Y.C. Yang, L.L. Szafraniec, W.T. Beaudry, D.K. Rohrbaugh, L.R. Procell, J.B. Samuel, J. Org. Chem. 1996, 61, 8407.
6. a) J. Epstein, J.J. Callahan, V.E. Bauer, Phosphorus 1974, 4, 157;
7. b) J. Epstein, P.L. Cannon Jr, J.R. Sowa, J. Am. Chem. Soc. 1970, 92, 7390.
8. a) F.M. Menger, M.J. Rourk, Langmuir 1999, 15, 309;
9. b) C.A. Bunton, H.J. Foroudian, N.D. Gillitt, C.R. Whiddon, Can. J. Chem. 1998, 76, 946.
10. a) E. Le Guével, G. Moutiers, F. Terrier, L. Villien, Fr. Pat. No. 2769234; 9/29/99 Eur. Patent No. 98402407.5-2104.
11. C. Lion, M. Hedayatullah, C. Charvy, S. Briand, S. Vincent, L. Fosset, L. Delmas, G. Magnaud, M. Desgranges, H. Sentenac-Roumanou, Bull. Soc. Chim. Belg. 1995, 104, 515 and references therein.
12. a) C.D. Bedford, R.A. Howd, D.A. Goff, G.A. Koolpe, M. Petesch, A. Miller, H.W. Nolen III, H.A. Musallam, R.O. Pick, D.E. Jones, I. Koplovitz, W.E. Sultan, J. Med. Chem. 1989, 32, 493;
13. b) C.D. Bedford, R.N. Harris III, R.A. Howd, D.A. Goff, G.A. Koolpe, M. Petesch, I. Koplovitz, W.E. Sultan, H.A. Musallam, J. Med. Chem. 1989, 32, 504.
14. a) Y. Ashani, S. Cohen, J. Med. Chem. 1971, 14, 621;
15. b) Y. Ashani, S. Cohen, J. Med. Chem. 1968, 11, 967;
16. c) Y. Ashani, S. Cohen, Isr. J. Chem. 1967, 5, 59;
17. d) Y. Ashani, S. Cohen, J. Med. Chem. 1970, 13, 471.
18. a) F. Terrier, P. McCormack, E. Kizilian, J.C. Hallé, P. Demerseman, F. Guir, C. Lion, J. Chem. Soc. Perkin Trans.2 1991, 153;
19. b) F. Terrier, G. Moutiers, L. Xiao, E. Le Guével, F. Guir, J. Org. Chem. 1995, 60, 1748;
20. c) F. Degorre, D. Kiffer, F. Terrier, J. Med. Chem. 1988, 31, 757.
21. a) A.L. Green, B. Saville, J. Chem. Soc. 1956, 3887;
22. b) A.L. Green, G.L. Sainsbury, B. Saville, M. Stansfield, J. Chem. Soc. 1958, 1583.
23. a) M. Bralic, N. Radic, Analusis 1999, 27, 57;
24. b) H. Hara, K. Yabuchi, M. Higashida, M. Ogawa, Anal. Chim. Acta 1998, 364, 117.
25. D. Midgley, Ion-Sel. Electrode Rev. 1981, 3, 43.
26. a) K. Srinivasan, G.A. Rechnitz, Anal. Chem. 1968, 40, 1818;
27. b) F. Oehme, L. Dolezalova, Anal. Chem. 1970, 251, 1.
28. I.V Kuznetsova, S.S. Khmelev, O.V Sivanova, J. Anal. Chem. 1997, 52, 48.
29. M. Baret, P. Fabry, D.L. Massart, C. Menardo, M. Fraysse, Analusis 1998, 26, 267.
30. F. Terrier, in Nucleophilic Aromatic Displacement (Ed: H. Feuer), VCH, New York, 1991, ch. 1.
31. R substituion of the fluorine atom of DNFB by the 4-chlorophenoxide species, a slower decomposition of the resulting arylether leading to the 2,4-dinitrophenoxide ion was observed by stopped flow spectrophotometry. This finding agrees with previous reports by Miller et al. that the displacement step is the rate determining step of the overall decomposition of DNFB by phenoxide ions in water or methanol [19].
32. a) J. Miller, in Aromatic Nucleophilic Substitution, Elsevier, Amsterdam, 1968;
33. b) G.D. Leahy, M. Liverio, J. Miller, A.J. Parker, Aust. J. Chem. 1956, 9, 382.