Bis- and tris(amidine)fluoroboron cations and mixed tetrahaloborate anions: NMR studies of mixed boron trihalide adduct redistribution reactions involving amidines as strong nitrogen bases

Canadian Journal of Chemistry

Volumn 74, Issue 11, 1996, Pages 2131-2142

  Hartman, J Stephen ^a   Yuan, Zheng ^a,b   Fox, Arnold ^a,c   Nguyen, Anh ^a  

^a BROCK UNIVERSITY   (Canada)

^b Watkins Johnson Company   (United States)

^c General Ballistics   (Canada)

Author keywords

1,5 diazabicyclo 4,3,0 non 5 ene (DBN); 1,8 diazabicyclo 5,4,0 undec 7 ene (DBU); Amidines; Boron 11 NMR; Fluorine 19 NMR; Fluoroboron cations; Mixed boron trihalide adducts; Redistribution reactions

Indexed keywords

AMINES; BORON; COMPOSITION; ELECTRON ENERGY LEVELS; IONS; NITROGEN; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; SALTS; SUBSTITUTION REACTIONS;

AMIDINES; ELECTRON DELOCALIZATION; FLUOROBORON CATIONS; MIXED BORON TRIHALIDE ADDUCTS; REDISTRIBUTION REACTIONS;

ORGANIC COMPOUNDS;

EID: 0030289998     PISSN: 00084042     EISSN: None     Source Type: Journal    
DOI: 10.1139/v96-242     Document Type: Article

References (58)

1. M.J. Farquharson and J.S. Hartman. J. Chem. Soc. Chem. Commun. 256 (1984).
2. M.J. Farquharson and J.S. Hartman. Can. J. Chem. 67, 1711 (1989).
3. M.J. Farquharson and J.S. Hartman. Can. J. Chem. 74, 1309 (1996).
4. S. Patai and Z. Rappaport (Editors). The chemistry of functional groups. The chemistry of amidines and imidates. Vol. 2. John Wiley and Sons, New York. 1991.
5. J. Oszczpowicz and E. Raczynska. J. Chem. Soc. Perkin Trans. 2, 1643 (1984).
6. J. Oszczpowicz and K. Ciszkowski. J. Chem. Soc. Perkin Trans. 2, 663 (1987); E. Raczynska, J. Oszczpowicz, and M. Walczak. J. Chem. Soc. Perkin Trans. 2, 1087 (1985).
7. J. Oszczpowicz and K. Ciszkowski. J. Chem. Soc. Perkin Trans. 2, 663 (1987); E. Raczynska, J. Oszczpowicz, and M. Walczak. J. Chem. Soc. Perkin Trans. 2, 1087 (1985).
8. J. Barker and M. Kilner. Coord. Chem. Rev. 133, 219 (1994); K. Vrieze and G. Van Koten. In Comprehensive coordination chemistry. The synthesis, reactions, properties, and applications of coordination compounds. Vol. 2. Edited by G. Wilkinson, R.D. Gillard, and J.A. McCleverty. Pergamon Press, Oxford. 1987. Chap. 13, Sect. 13.5.
9. J. Barker and M. Kilner. Coord. Chem. Rev. 133, 219 (1994); K. Vrieze and G. Van Koten. In Comprehensive coordination chemistry. The synthesis, reactions, properties, and applications of coordination compounds. Vol. 2. Edited by G. Wilkinson, R.D. Gillard, and J.A. McCleverty. Pergamon Press, Oxford. 1987. Chap. 13, Sect. 13.5.
10. F.A. Cotton, T. Inglis, K. Milner, and T.R. Webb. Inorg. Chem. 14, 2023 (1975); F.A. Cotton, W.H. Ilsley, and W. Kaim. Inorg. Chem. 18, 3569 (1979).
11. F.A. Cotton, T. Inglis, K. Milner, and T.R. Webb. Inorg. Chem. 14, 2023 (1975); F.A. Cotton, W.H. Ilsley, and W. Kaim. Inorg. Chem. 18, 3569 (1979).
12. H. Oediger, F. Möller, and K. Eiter. Synthesis, 591 (1972).
13. I. Hermecz. Adv. Heterocycl. Chem. 42, 84 (1987).
14. D.H.R. Barton, J.D. Elliott, and S.D. Géro. J. Chem. Soc. Perkin Trans. 1, 2085 (1982).
15. D.R. Perrin. Dissociation constants of organic bases in aqueous solutions. Butterworths, London. 1965; and Supplement, 1972.
16. H. Lammers, P. Cohen-Fernandes, and C.L. Habraken. Tetrahedron, 50, 865 (1994).
17. R. Reed, R. Reau, F. Dahan, and G. Bertrand. Angew. Chem. Int. Ed. Engl. 32, 399 (1993); G. Bouhadir, R.W. Reed, R. Reau, and G. Bertrand. Heteroat. Chem. 6, 371 (1995); H.H. Karsch, T. Rupprich, and M. Heckel. Chem. Ber. 128, 959 (1995).
18. R. Reed, R. Reau, F. Dahan, and G. Bertrand. Angew. Chem. Int. Ed. Engl. 32, 399 (1993); G. Bouhadir, R.W. Reed, R. Reau, and G. Bertrand. Heteroat. Chem. 6, 371 (1995); H.H. Karsch, T. Rupprich, and M. Heckel. Chem. Ber. 128, 959 (1995).
19. R. Reed, R. Reau, F. Dahan, and G. Bertrand. Angew. Chem. Int. Ed. Engl. 32, 399 (1993); G. Bouhadir, R.W. Reed, R. Reau, and G. Bertrand. Heteroat. Chem. 6, 371 (1995); H.H. Karsch, T. Rupprich, and M. Heckel. Chem. Ber. 128, 959 (1995).
20. J.V. Barkley, C.J. Davies, B.T. Heaton, and C. Jacob. J. Chem. Soc. Dalton Trans. 2861 (1995), and references therein.
21. D.F. Shriver. The manipulation of air-sensitive compounds. McGraw-Hill, New York. 1969.
22. J.D. Wilson, J.S. Wager, and H. Weingarten. J. Org. Chem. 36, 1613 (1971).
23. D.C. Bradley and I.M. Thomas. J. Chem. Soc. 3857 (1960).
24. A. Fox, J.S. Hartman, and R.E. Humphries. J. Chem. Soc. Dalton Trans. 1275 (1982).
25. J.M. Miller. Mass Spectrom. Rev. 9, 319 (1990); K. Balasanmugam, J.S. Hartman, J.M. Miller, and Z. Yuan. Can. J. Chem. 67, 685 (1989).
26. J.M. Miller. Mass Spectrom. Rev. 9, 319 (1990); K. Balasanmugam, J.S. Hartman, J.M. Miller, and Z. Yuan. Can. J. Chem. 67, 685 (1989).
27. R.K. Harris. Nuclear magnetic resonance spectroscopy. Pitman, London. 1983. Chap. 7.
28. J.S. Hartman and G.J. Schrobilgen. Inorg. Chem. 11, 940 (1972).
29. J. Bacon, R.J. Gillespie, and J.W. Quail. Can. J. Chem. 41, 3063 (1963); M.J. Bula and J.S. Hartman. J. Chem. Soc. Dalton Trans. 1047 (1973).
30. J. Bacon, R.J. Gillespie, and J.W. Quail. Can. J. Chem. 41, 3063 (1963); M.J. Bula and J.S. Hartman. J. Chem. Soc. Dalton Trans. 1047 (1973).
31. M.A. Mathur and G.E. Ryschkewitsch. Inorg. Chem. 19, 887 (1980).
32. C. Makosky, G.L. Galloway, and G.E. Ryschkewitsch. Inorg. Chem. 6, 1972 (1967).
33. J. Emri and B. Györi. In Comprehensive coordination chemistry. The synthesis, reactions, properties, and applications of coordination compounds. Vol. 3. Edited by G. Wilkinson, R.D. Gillard, and J.A. McCleverty. Pergamon Press, Oxford. 1987. Chap. 24, pp. 81-104; G.E. Ryschkewitsch. In Boron hydride chemistry. Edited by E.L. Muetterties. Academic Press, New York. 1975. Chap. 6.
34. J. Emri and B. Györi. In Comprehensive coordination chemistry. The synthesis, reactions, properties, and applications of coordination compounds. Vol. 3. Edited by G. Wilkinson, R.D. Gillard, and J.A. McCleverty. Pergamon Press, Oxford. 1987. Chap. 24, pp. 81-104; G.E. Ryschkewitsch. In Boron hydride chemistry. Edited by E.L. Muetterties. Academic Press, New York. 1975. Chap. 6.
35. E. D. Becker. High resolution NMR. Theory and chemical applications. 2nd ed. Academic Press, New York. 1980. Chap. 5, pp. 93-94.
36. K. Kuhlmann and D.M. Grant. J. Phys. Chem. 68, 3208 (1964); R.J. Gillespie and J.S. Hartman. J. Chem. Phys. 45, 2712 (1966).
37. K. Kuhlmann and D.M. Grant. J. Phys. Chem. 68, 3208 (1964); R.J. Gillespie and J.S. Hartman. J. Chem. Phys. 45, 2712 (1966).
38. R.J. Gillespie and J.S. Hartman. Can. J. Chem. 46, 2147 (1968).
39. P.E. Hansen. Annu. Rep. NMR Spectrosc. 15, 105 (1983); G.A. Webb. In NMR of newly accessible nuclei. Vol. 1. Edited by P. Laszlo. Academic Press, New York. 1983. Chap. 4, pp. 94-95.
40. P.E. Hansen. Annu. Rep. NMR Spectrosc. 15, 105 (1983); G.A. Webb. In NMR of newly accessible nuclei. Vol. 1. Edited by P. Laszlo. Academic Press, New York. 1983. Chap. 4, pp. 94-95.
41. H. Nöth and B. Wrackmeyer. In Nuclear magnetic resonance spectroscopy of boron compounds. NMR. Basic principles and progress. Vol. 14. Edited by P. Diehl, E. Fluck, and R. Kosfeld. Springer-Verlag, Berlin. 1978. Table XI.
42. J.S. Hartman and J.M. Miller. Adv. Inorg. Chem. Radiochem. 21, 147 (1978).
43. M.J. Bula, D.E. Hamilton, and J.S. Hartman. J. Chem. Soc. Dalton Trans. 1405 (1972).
44. M.J. Bula, J.S. Hartman, and C.V. Raman. J. Chem. Soc. Dalton Trans. 725 (1974).
45. J.S. Hartman and B.D. McGarvey. Inorg. Chim. Acta 44, L39 (1980); J.S. Hartman, B.D. McGarvey, and C.V. Raman. Inorg. Chim. Acta 49, 63 (1981).
46. J.S. Hartman and B.D. McGarvey. Inorg. Chim. Acta 44, L39 (1980); J.S. Hartman, B.D. McGarvey, and C.V. Raman. Inorg. Chim. Acta 49, 63 (1981).
47. J.S. Hartman and G.J. Schrobilgen. Inorg. Chem. 13, 874 (1974).
48. Gmelin handbook of inorganic chemistry. Boron compounds. 2nd Supplement, Vol. 37. 1976. pp. 114-125.
49. J.S. Hartman and J.M. Miller. Inorg. Chem. 13, 1467 (1974).
50. (a) J. Oszczapowicz, I. Wawer, M. Dargatz, and E. Kleinpeter. J. Chem. Soc. Perkin Trans. 2, 1127 (1995), and references therein;
51. 15N NMR spectroscopy. NMR. Basic principles and progress. Vol. 18. Edited by P. Diehl, E. Fluck, and R. Kosfeld. Springer-Verlag, Berlin. 1981. Fig. 1-1.
52. A.G. Massey. Adv. Inorg. Chem. Radiochem. 10, 1 (1967).
53. J.S. Hartman and P. Stilbs. J. Chem. Soc. Chem. Commun. 566 (1975).
54. A.F. Janzen. Coord. Chem. Rev. 130, 355 (1994); X. Ou, R. Wallace, and A.F. Janzen. Can. J. Chem. 71, 51 (1993).
55. A.F. Janzen. Coord. Chem. Rev. 130, 355 (1994); X. Ou, R. Wallace, and A.F. Janzen. Can. J. Chem. 71, 51 (1993).
56. H.C. Brown. J. Chem. Soc. 1248 (1956).
57. J. March. Advanced organic chemistry. Reactions, mechanisms, and structure. 4th ed. John Wiley and Sons, New York. 1992. pp. 195-202; T.L. Gilchrist and C.W. Rees. Carbenes, nitrenes and arynes. Thomas Nelson and Sons, London. 1969. Chap. 2.
58. J. March. Advanced organic chemistry. Reactions, mechanisms, and structure. 4th ed. John Wiley and Sons, New York. 1992. pp. 195-202; T.L. Gilchrist and C.W. Rees. Carbenes, nitrenes and arynes. Thomas Nelson and Sons, London. 1969. Chap. 2.