Reactions of phosphorus trifluoride with anionic nucleophiles in the gas phase

European Journal of Mass Spectrometry

Volumn 2, Issue 4-5, 1996, Pages 225-231

  Smith, Jacob D ^a   O'Hair, Richard A J ^a,b  

^a KANSAS STATE UNIVERSITY   (United States)

^b UNIVERSITY OF MELBOURNE   (Australia)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0041968291     PISSN: 14690667     EISSN: None     Source Type: Journal    
DOI: 10.1255/ejms.56     Document Type: Article

References (33)

1. R.A.J. O'Hair, "Gas Phase Positive and Negative Ion Chemistry of Organophosphorus Compounds via Mass Spectrometric Techniques", in The Chemistry of Organophosphorus Compounds - Volume 4, Ed by F.R. Hartley. John Wiley & Sons, Chichester, Chapter 8, p. 731 (1996).
2. J.J. Grabowski, P.D. Roy and R. Leone, J. Chem. Soc. Perkin Trans. II 1627 (1988).
3. D.R. Anderson, C.H. DePuy, J. Filley and V.M. Bierbaum, J. Am. Chem. Soc. 106, 6513 (1984).
4. (a) S.A. Sullivan and J.L. Beauchamp, Inorg. Chem. 17, 1589 (1978);
5. (b) J.W. Larson and T.B. McMahon, Inorg. Chem. 26, 4018 (1987).
6. R.C. Lum and J.J. Grabowski, J. Am. Chem. Soc. 114, 8619 (1992).
7. R.C. Lum and J.J. Grabowski, J. Am. Chem. Soc. 114, 9663 (1992).
8. T.M. Miller, A.E. Stevens Miller, A.A. Viggiano, R.A. Morris and J.F. Paulson, J. Chem. Phys. 100, 7200 (1994).
9. R.A.J. O'Hair, J.C. Sheldon and J.H. Bowie, J. Chem. Soc., Dalton Trans. 2837 (1988).
10. (a) R.N. McDonald, M.T. Jones and A.K. Chowdhury, J. Am. Chem. Soc. 113, 476 (1991);
11. (b) R.N. McDonald and A.K. Chowdhury, J. Am. Chem. Soc. 107, 4123 (1985);
12. (c) R.N. McDonald, A.K. Chowdhury and D.W. Setser, J. Am. Chem. Soc. 102, 6491 (1980).
13. J.D. Smith, M.S. Thesis, Kansas State University (1996).
14. Y. Ikezoe, S. Matsuoka, M. Takebe and A. Viggiano, Gas Phase Ion-Molecule Reaction Rate Constants Through 1986. Ion Reaction Research Group, Tokyo (1987).
15. Gas-phase acidities and other thermochemistry are taken from: (a) NIST Standard Reference Database 19B: NIST Negative Ion Energetics Database Version 2.07, Program written/data compilation by John E. Bartmess, Department of Chemistry, University of Tennessee, Knoxville, TN 37996-1600. This compilation is based on original data from: S.G. Lias, J.E. Bartmess, J.F. Liebman, J.L. Holmes, R.D. Levin, W.G. Mallard, "Gas-phase Ion and Neutral Thermochemistry", J. Phys. Chem. Ref. Data Vol. 17, Suppl. 1 (1988); (b) G. Pilcher, "Thermochemistry of Phosphorus (III) Compounds", in The Chemistry of Organophosphorus Compounds - Volume 1, Ed by F.R. Hartley. John Wiley & Sons, Chichester, Chapter 5, p. 127 (1990).
16. Gas-phase acidities and other thermochemistry are taken from: (a) NIST Standard Reference Database 19B: NIST Negative Ion Energetics Database Version 2.07, Program written/data compilation by John E. Bartmess, Department of Chemistry, University of Tennessee, Knoxville, TN 37996-1600. This compilation is based on original data from: S.G. Lias, J.E. Bartmess, J.F. Liebman, J.L. Holmes, R.D. Levin, W.G. Mallard, "Gas-phase Ion and Neutral Thermochemistry", J. Phys. Chem. Ref. Data Vol. 17, Suppl. 1 (1988); (b) G. Pilcher, "Thermochemistry of Phosphorus (III) Compounds", in The Chemistry of Organophosphorus Compounds - Volume 1, Ed by F.R. Hartley. John Wiley & Sons, Chichester, Chapter 5, p. 127 (1990).
17. Gas-phase acidities and other thermochemistry are taken from: (a) NIST Standard Reference Database 19B: NIST Negative Ion Energetics Database Version 2.07, Program written/data compilation by John E. Bartmess, Department of Chemistry, University of Tennessee, Knoxville, TN 37996-1600. This compilation is based on original data from: S.G. Lias, J.E. Bartmess, J.F. Liebman, J.L. Holmes, R.D. Levin, W.G. Mallard, "Gas-phase Ion and Neutral Thermochemistry", J. Phys. Chem. Ref. Data Vol. 17, Suppl. 1 (1988); (b) G. Pilcher, "Thermochemistry of Phosphorus (III) Compounds", in The Chemistry of Organophosphorus Compounds - Volume 1, Ed by F.R. Hartley. John Wiley & Sons, Chichester, Chapter 5, p. 127 (1990).
18. (a) T. Su and M.T. Bowers, Int. J. Mass Spectrom. Ion Phys. 12, 347 (1973);
19. (b) K.J. Miller and J.A. Savchik, J. Am. Chem. Soc. 101, 7206 (1979).
20. R. Damrauer, C.H. DePuy and V.M. Bierbaum, Organomet. 1, 1553 (1982).
21. 1).
22. R. Engel, Synthesis of Carbon-Phosphorous Bonds. CRC Press Inc., Boca Raton, Florida (1988).
23. For previous chemical probes of "O" versus "C" reactivity of ambident enolate anions see: (a) M.D. Brickhouse and R.R. Squires, J. Phys. Org. Chem. 2, 389 (1989); (b) I.L. Freriks, L.J. de Koning and N.M.M. Nibbering, J. Am. Chem. Soc. 113, 9119 (1991); (c) B.D. Wladkowski, J.L. Wilbur, M. Zhong and J.I. Brauman, J. Am. Chem. Soc. 115, 8833 (1993).
24. For previous chemical probes of "O" versus "C" reactivity of ambident enolate anions see: (a) M.D. Brickhouse and R.R. Squires, J. Phys. Org. Chem. 2, 389 (1989); (b) I.L. Freriks, L.J. de Koning and N.M.M. Nibbering, J. Am. Chem. Soc. 113, 9119 (1991); (c) B.D. Wladkowski, J.L. Wilbur, M. Zhong and J.I. Brauman, J. Am. Chem. Soc. 115, 8833 (1993).
25. For previous chemical probes of "O" versus "C" reactivity of ambident enolate anions see: (a) M.D. Brickhouse and R.R. Squires, J. Phys. Org. Chem. 2, 389 (1989); (b) I.L. Freriks, L.J. de Koning and N.M.M. Nibbering, J. Am. Chem. Soc. 113, 9119 (1991); (c) B.D. Wladkowski, J.L. Wilbur, M. Zhong and J.I. Brauman, J. Am. Chem. Soc. 115, 8833 (1993).
26. A reviewer has suggested a third possible type of structure for the adduct, viz. the fluroride ion-molecule complex shown as (C) in Scheme 1.
27. We recognize the dangers of oversimplifying the picture since the prediction of the gas-phase acidity of a species (A-H) is complicated by the fact that the acidity is influenced by both the electron affinity of A and the homolytic bond dissociation energy of A-H. For a discussion with relevance to phosphorus species, see: S. Berger and J.I. Brauman, J. Am. Chem. Soc. 114, 4737 (1992).
28. -1: C.E. Allison and T.B. McMahon, J. Am. Chem. Soc. 112, 1672 (1990).
29. (a) R.G. Cavell, J. Chem. Soc. 1992 (1964);
30. (b) J.S. Harman and D.W.A. Sharp, J. Chem. Soc. (A) 1935 (1970).
31. R.R. Holmes and R.P. Wagner, Inorg. Chem. 2, 384 (1963).
32. R.A.J. O'Hair, M. Krempp, R. Damrauer and C.H. DePuy, Inorg. Chem. 31, 2092 (1992).
33. S. Gronert, R.A.J. O'Hair, S. Prodnuk, D. Sülzle, R. Damrauer and C.H. DePuy, J. Am. Chem. Soc. 112, 997 (1990).