Protonation and deprotonation of hydroxamic acids. An MO ab initio study

Journal of Molecular Structure: THEOCHEM

Volumn 360, Issue 1-3, 1996, Pages 109-117

  Yamin, Lazaro J ^a   Ponce, Carlos A ^a   Estrada, Mario R ^a   Vert, Francisco Tomas ^b  

^a UNIVERSIDAD NACIONAL DE SAN LUIS   (Argentina)

^b UNIVERSITY OF VALENCIA   (Spain)

Author keywords

Deprotonation; Hydroxamic acid; Protonation

Indexed keywords

EID: 0001377395     PISSN: 01661280     EISSN: None     Source Type: Journal    
DOI: 10.1016/0166-1280(95)04281-4     Document Type: Article

References (72)

1. L. Bauer and O. Exner, Angew. Chem., Int. Ed. Engl., 13 (1974) 376.
2. R.T. Coutts, Can. J. Pharm. Sci. 1 (1967) 27.
3. (a) W. Cohen and B.F. Erlander, J. Am. Chem. Soc., 82 (1960) 3928.
4. (b) D. Dell, D.R. Boreham and B.K. Martin, J. Pharm. Sci., 60 (1971) 1368.
5. (c) A. Goldstein, L. Aronow and S.M. Kalmerz, Principles of Drug Action, Harper and Row, New York, 1969.
6. (d) K. Kumaki, S. Tomioka, K. Kobashi and J. Hase, J. Chem. Pharm. Bull., 20 (1972) 1599.
7. (a) S. Mizukami and K. Nagata, Coord. Chem. Rev., 3 (1968) 267.
8. (b) T.J. King and P.G. Harrison, J. Chem. Soc., Chem. Commun., 13 (1972) 815.
9. (c) R.C. Michaelson, R.E. Palermo and K.B. Sharpless, J. Am. Chem. Soc., 99 (1977) 1990.
10. (a) R. Hilal and H. Moustafa, Int. J. Quantum Chem., 26 (1984) 183.
11. (b) M.T. Nguyen and T.K. Ha, J. Mol. Struct., (Theochem), 88 (1982) 127.
12. (c) E. Lipczyñska-Kochany and H. Iwamura, J. Org. Chem., 47 (1982) 5277.
13. (d) N.J. Fitzpatrick and R. Mageswaran, Polyhedron, 8 (1989) 2255.
14. (e) T. Turi, J.J. Dannenberg, J. Rama and O.N. Ventura, J. Phys. Chem., 96 (1992) 3709.
15. (a) I.K. Larsen and O. Exner, Chem. Commun., (1970) 254.
16. (b) I.K. Larsen, Acta Chem. Scand., 25 (1971) 2409.
17. (c) O. Exner, V. Jehlicka and A. Reiser, Collect. Czech. Chem. Commun., 24 (1959) 3207.
18. (a) D.A. Brown, W.K. Glass, R. Mageswaran and B. Girmay, Magn. Reson. Chem., 26 (1988) 970.
19. (b) I.K. Larsen, Acta Crystallogr., Sect. B, 44 (1988) 527.
20. (c) B.H. Bracher and R.W. Small, Acta Crystallogr., 26 (1970) 1705.
21. (a) M. Davies and N.A. Spiers, Spectrochim. Acta, 15 (1959) 487.
22. (b) J.P. Freeman, J. Am. Chem. Soc., 80 (1958) 5954.
23. (c) D. Hadzi and D. Prevorsek, Spectrochim. Acta, 10 (1957) 38.
24. (a) F. Di Furia, G. Modena and P. Scrinun, Nouv. J. Chim., 8 (1984) 45.
25. (b) A. Levi, G. Modena and G. Scorrano, J. Am. Chem. Soc., 96 (1974) 6585.
26. (c) A.M. Lobo, S. Probhakar, M.T,C, Fonseca and A.M.B. Rodriguez, Tetrahedron Lett., (1977) 3167.
27. (a) D.C. Berndt and J.K. Sharp, J. Org. Chem., 38 (1973) 346.
28. (b) M. Dessolin and M. Laloi-Diard, Bull. Soc. Chim. Fr., (1971) 2946.
29. (c) M. Dessolin, M. Laloi-Diard and M. Vilkas, Bull. Soc. Chim. Fr., (1970) 2573.
30. (d) G.M. Steinberg and R. Surdler, J. Ord. Chem., 30 (1965) 2362.
31. (a) R.E. Plapinger, J. Org. Chem., 24 (1959) 802.
32. (b) O. Exner, Collect. Czech. Chem. Commun., 29 (1964) 1337.
33. R. Ditchfield, W.J. Hehre and J.A. Pople, J. Chem. Phys., 54 (1971) 724.
34. R.A. Poitier and M.R. Peterson, MONSTERGAUSS Program, University of Toronto, 1988.
35. P.C. Hariharen and J.A. Pople, Theor. Chim. Acta, 28 (1973) 213.
36. I. Mayer, Int. J. Quantum Chem., 29 (1986) 477.
37. (a) A.C. Hopkinson, K. Yates and I.G. Csizmadia, J. Chem. Phys., 52 (1979) 1784.
38. (b) L.A. Allen and W.L. Jorgenson, J. Am. Chem. Soc., 93 (1971) 567.
39. (a) F. Mathis, C.R. Acad. Sci., Ser. A, 232 (1951) 505.
40. (b) D. Monnier and C. Jegge, Helv. Chim. Acta, 40 (1957) 513.
41. (c) O. Exner and B. Kabác, Collect. Czech. Chem. Commun., 28 (1963) 1656.
42. (a) O. Exner, Collect. Czech. Chem. Commun., 21 (1956) 1500.
43. (b) A.J. Buglass, K. Hudson and J.G. Tillet, J. Chem. Soc. B, (1971) 123.
44. (c) D.C. Berndt and R.L. Fuller, J. Org. Chem., 31 (1966) 3312.
45. J. Del Bene, J. Am. Chem. Soc., 99 (1977) 3619.
46. (a) J.I. Brareman and L.K. Slair, J. Am. Chem. Soc., 91 (1969) 2126;
47. (b) M.S.B. Munson, J. Am. Chem. Soc., 87 (1965) 2332.
48. (a) D.H. Aue, H.M. Webb and M.T. Bowers, J. Am. Chem. Soc., 94 (1972) 4726.
49. (b) M.T. Bowers, D.H. Aue, H.M. Webb and R.T. McIver, J. Am. Chem. Soc., 93 (1971) 4313.
50. (a) L. Radom, Mod. Theor. Chem., 4 (1977) 333.
51. (b) A.C. Hopkinson, Prog. Theor. Org. Chem., 2 (1977) 1944.
52. (c) J. Simons, An. Rev. Phys. Chem., 28 (1977) 15.
53. (a) C.E. Bartmess and R.T. McIver, Jr., Gas Phase Ion Chem., 2 (1979) 88.
54. (b) B.K. Janousek and J.I. Brauman, Gas Phase Ion Chem., 2 (1979) 53.
55. (a) C.E. Dykstra, M. Hereld, R.R. Luchesse, H.F. Schaefer and W. Meyer, J. Chem. Phys., 67 (1977) 4071.
56. (b) R.B. Davidson and M.L. Hudak, J. Am. Chem. Soc., 99 (1977) 3918.
57. (c) H. Kolmar, J. Am. Chem. Soc., 100 (1978) 2665.
58. (d) R. Bonaccorsi, C. Petrongolo, E. Scrocco and J. Tomasi, Chem. Phys. Lett., 3 (1969) 473.
59. (e) C.E. Dykstra, A.J. Arduendo and T. Fukunaga, J. Am. Chem. Soc., 100 (1978) 6007.
60. (f) J.K. Wilmshurst and C.E. Dykstra, J. Am. Chem. Soc., 102 (1980) 4668.
61. (g) R.A. Eades, P.G. Gassman and D.A. Dixon, J. Am. Chem. Soc., 103 (1981) 1066.
62. (h) J. Chandrasekhar, J.G. Andrade and P.v.R. Schleyer, J. Am. Chem. Soc., 103 (1981) 5612.
63. (a) A.C. Hopkinson, M.H. Lien, K. Yates, P.G. Mezey and I.G. Csizmadia, J. Chem. Phys., 67 (1977) 517.
64. (b) N.L. Summers and J. Tyrell, J. Am. Chem. Soc., 99 (1977) 3960.
65. (c) A.L. Hinde, A. Pross and L. Radom, J. Comput. Chem., 1 (1980) 118.
66. (d) A. Pross, D.E. DeFrees, B.A. Levi, S.K. Pollak, L. Radom and W.J. Hehre, J. Org. Chem., 46 (1981) 693.
67. (a) T.B. McMahon and P. Kebarle, J. Am. Chem. Soc., 98 (1976) 3399.
68. (b) D.K. Bohme, E. Lee-Ruff and L.B. Young, J. Am. Chem. Soc., 94 (1972) 5153.
69. (a) B.E. Hackley, Jr., R. Plapinger, M. Stolberg and T. Wagner-Jauregg, J. Am. Chem. Soc., 77 (1955) 3651.
70. (b) R. Swidler and G.M. Steinberg, J. Am. Chem. Soc., 78 (1956) 3594.
71. (c) G.M. Steinberg and R. Swidler, J. Org. Chem., 30 (1965) 2362.
72. M. Decouzon, O. Exner, J.F. Gal and P.Ch. Maria, J. Org. Chem., 55 (1990) 3980.