An experimental and computational study of the ions formed by the reaction of cyclopentanone with O•-

International Journal of Mass Spectrometry

Volumn 241, Issue 2-3 SPEC.ISS., 2005, Pages 149-163

  Hoenigman, Rebecca L ^a,b   Kato, Shuji ^b   Borden, Weston Thatcher ^a,c   Bierbaum, Veronica M ^b,c  

^a UNIVERSITY OF WASHINGTON   (United States)

^b UNIVERSITY OF COLORADO   (United States)

^c UNIVERSITY OF NORTH TEXAS   (United States)

Author keywords

Cyclopentanone; Density functional theory; Didehydro radical anion; Electron affinity; Proton affinity

Indexed keywords

CYCLOPENTANONE DERIVATIVE; ION; OXYGEN; PROTON;

ARTICLE; BINDING AFFINITY; CALCULATION; CHEMICAL REACTION; DENSITY FUNCTIONAL THEORY; ELECTRON; ELECTRON TRANSPORT; ENERGY; GAS; MATHEMATICAL COMPUTING; STRUCTURE ANALYSIS;

EID: 15944365815     PISSN: 13873806     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.ijms.2004.12.009     Document Type: Article

References (76)

1. P.J. Chenier J. Chem. Ed. 55 1978 286
2. L.J. Schaad, B.A. Hess Jr., and R. Zahradnik J. Org. Chem. 46 1981 1909
3. For review, see
4. K. Schaffner, and M. Demuth P. de Mayo Rearrangements in Ground and Excited States vol. 3 1980 Academic Press New York
5. A.G. Schultz, M. Macielag, and M. Plummer J. Org. Chem. 53 1988 391
6. F.G. West, C. Hartke-Karger, D.J. Koch, C.E. Kuehn, and A.M. Arif J. Org. Chem. 58 1993 6795
7. R. Hoffmann J. Am. Chem. Soc. 90 1968 1475
8. D.B. Sclove, J.F. Pazos, R.L. Camp, and F.D. Greene J. Am. Chem. Soc. 92 1970 7488
9. T.H. Chan, and B.S. Ong J. Org. Chem. 43 1978 2994
10. T.H. Chan, and B.S. Ong Tetrahedron 36 1980 2269
11. F. Turecek, D.E. Drinkwater, and F.W. McLafferty J. Am. Chem. Soc. 113 1991 5950
12. For reviews, see
13. P. Dowd Acc. Chem. Res. 5 1972 242
14. J.A. Berson Acc. Chem. Res. 11 1978 446
15. J.A. Berson W.T. Borden Diradicals 1982 Wiley New York
16. For reviews, see
17. W.T. Borden W.T. Borden Diradicals 1982 Wiley New York
18. W.T. Borden P.M. Lahti Magnetic Properties of Organic Materials 1999 Marcel Dekker New York
19. P. Dowd J. Am. Chem. Soc. 88 1966 2587
20. R.J. Baseman, D.W. Pratt, M. Chow, and P. Dowd J. Am. Chem. Soc. 98 1976 5726
21. P.G. Wenthold, J. Hu, R.R. Squires, and W.C. Lineberger J. Am. Chem. Soc. 118 1996 475
22. Y. Osamura, W.T. Borden, and K. Morokuma J. Am. Chem. Soc. 106 1984 5112
23. M.B. Coolidge, K. Yamashita, K. Morokuma, and W.T. Borden J. Am. Chem. Soc. 112 1990 1751
24. C.A. Schalley, S. Blanksby, J.N. Harvey, D. Schröder, W. Zummack, J.H. Bowie, and H. Schwarz Eur. J. Org. Chem. 1998 987
25. A.S. Ichimura, P.M. Lahti, and A.R. Matlin J. Am. Chem. Soc. 112 1990 2868
26. H.K. Powell, and W.T. Borden J. Org. Chem. 60 1995 2654
27. D. Lim, D.A. Hrovat, W.T. Borden, and W.L. Jorgensen J. Am. Chem. Soc. 116 1994 3494
28. A.R. Matlin, P.M. Lahti, D. Appella, A. Straumanis, S. Lin, H. Patel, K. Jin, K.P. Schrieber, J. Pauls, and P. Raulerson J. Am. Chem. Soc. 121 1999 2164
29. A.P. Masters, M. Parvez, T.S. Sorensen, and F. Sun J. Am. Chem. Soc. 116 1994 2804
30. T. Hirano, T. Kumagai, T. Miyashi, K. Akiyama, and Y. Ikegami J. Org. Chem. 56 1991 1907
31. K.M. Ervin, and W.C. Lineberger N.G. Adams L.M. Babcock Advances in Gas Phase Ion Chemistry vol. 1 1992 JAI Press Greenwich, CT
32. J. Lee, and J.J. Grabowski Chem. Rev. 92 1992 1611
33. For review, see M. Born, S. Ingemann, and N.M.M. Nibbering Mass Spectrom. Rev. 16 1997 181
34. J.H.J. Dawson, A.J. Noest, and N.M.M. Nibbering Int. J. Mass Spectrom. Ion Phys. 30 1979 189
35. L.J. Bellamy The Infrared Spectra of Complex Molecules 1975 Wiley New York p. 168
36. A.G. Harrison, and K.R. Jennings J. Chem. Soc., Faraday Trans. 1 72 1976 1601
37. M. Lin, and J.J. Grabowski Int. J. Mass Spectrom. 237 2004 147
38. J.M. Van Doren, S.E. Barlow, C.H. DePuy, and V.M. Bierbaum Int. J. Mass Spectrom. Ion Process. 81 1987 85
39. V.M. Bierbaum M.L. Gross R. Caprioli P.B. Armentrout The Encyclopedia of Mass Spectrometry: vol. 1. Theory and Ion Chemistry 2003 Elsevier San Diego 98
40. Unless otherwise noted, all thermochemical data come from: P.J. Linstrom, W.G. Mallard (Eds.), NIST Chemistry WebBook, NIST Standard Reference Database Number 69, National Institute of Standards and Technology, Gaithersburg, MD, March 2003 (http://webbook.nist.gov).
41. T. Su, and W.J. Chesnavich J. Chem. Phys. 76 1982 5183
42. T.B. Malloy Jr., R.M. Hedges, and F. Fisher J. Org. Chem. 35 1970 4256
43. F.G. Gault, J.E. Germain, and J.-M. Conia Bull. Soc. Chim. France 1957 1064
44. J.-M. Conia Bull. Soc. Chim. France 1950 537
45. H.O. House, and B.M. Trost J. Org. Chem. 30 1965 2502
46. A.D. Becke J. Chem. Phys. 98 1993 5648
47. C. Lee, W. Yang, and R.G. Parr Phys. Rev. B 37 1988 785
48. For review, see W.T. Borden, and E.R. Davidson Acc. Chem. Res. 29 1996 67
49. K. Andersson, P.-A. Malmqvist, and B.O. Roos J. Chem. Phys. 96 1992 1218
50. P.C. Hariharan, and J.A. Pople Theor. Chim. Acta 28 1973 213
51. T. Clark, J. Chandrasekhar, G.W. Spitznagel, and P.V.R. Schleyer J. Comput. Chem. 4 1983 294
52. M.J. Frisch, G.W. Trucks, H.B. Schlegel, G.E. Scuseria, M.A. Robb, J.R. Cheeseman, V.G. Zakrzewski, J.A. Montgomery Jr., R.E. Stratmann, J.C. Burant, S. Dapprich, J.M. Millam, A.D. Daniels, K.N. Kudin, M.C. Strain, O. Farkas, J. Tomasi, V. Barone, M. Cossi, R. Cammi, B. Mennucci, C. Pomelli, C. Adamo, S. Clifford, J. Ochterski, G.A. Petersson, P.Y. Ayala, Q. Cui, K. Morokuma, D.K. Malick, A.D. Rabuck, K. Raghavachari, J.B. Foresman, J. Cioslowski, J.V. Ortiz, A.G. Baboul, B.B. Stefanov, G. Liu, A. Liashenko, P. Piskorz, I. Komaromi, R. Gomperts, R.L. Martin, D.J. Fox, T. Keith, M.A. Al-Laham, C.Y. Peng, A. Nanayakkara, C. Gonzalez, M. Challacombe, P.M.W. Gill, B. Johnson, W. Chen, M.W. Wong, J.L. Andres, C. Gonzalez, M. Head-Gordon, E.S. Replogle, J.A. Pople, Gaussian 98, Revision A.7, Gaussian, Inc., Pittsburgh, PA, 1998.
53. K. Andersson, P. Borowski, P. Boussard, M.P. Fülscher, G. Karlström, R. Lindh, P.-A. Malmqvist, J. Olsen, B.O. Roos, A.J. Sadlej, M. Schütz, L. Seijo, P.-O. Widmark, MOLCAS, Version 4.1, Department of Theoretical Chemistry, Chemical Centre, University of Lund, Lund, Sweden, 1999.
54. For review, see
55. J.C. Rienstra-Kiracofe, G.S. Tschumper, H.F. Schaefer III, S. Nandi III, and G.B. Ellison Chem. Rev. 102 2002 231
56. For examples, see
57. B.T. Hill, and R.R. Squires J. Chem. Soc., Perkin Trans. 2 1998 1027
58. J.C. Rienstra-Kiracofe, D.E. Graham, and H.F. Schaefer III Mol. Phys. 94 1998 767
59. S.T. Brown, J.C. Rienstra-Kiracofe, and H.F. Schaefer III J. Phys. Chem. A 103 1999 4065
60. C. Pak, J.C. Rienstra-Kiracofe, and H.F. Schaefer III J. Phys. Chem. A 104 2000 11232
61. S.C. Boesch, A.K. Grafton, and R.A. Wheeler J. Phys. Chem. 100 1996 10083
62. G.A. Russell, and G.R. Stevenson J. Am. Chem. Soc. 93 1971 2432
63. I.H. Elson, T.J. Kemp, D. Greatorex, and H.D.B. Jenkins Trans. Faraday Soc. II 69 1973 665
64. D.A. Plattner, and K.N. Houk J. Am. Chem. Soc. 117 1995 4405
65. H.L. Woodcock, H.F. Schaefer III, and P.R. Schreiner J. Phys. Chem. A 106 2002 11923
66. P.G. Wenthold, and R.R. Squires J. Am. Chem. Soc. 116 1994 6401
67. P.G. Wenthold, J. Hu, B.T. Hill, and R.R. Squires Int. J. Mass Spectrom. 179/180 1998 173
68. T. Bally, and W.T. Borden K.B. Lipkowitz D.B. Boyd Reviews in Computational Chemistry vol. 13 1999 Wiley New York
69. M. Harmata, and D.R. Lee J. Am. Chem. Soc. 124 2002 14328
70. See also
71. Z.C. Etheridge, and S. Caddick Tetrahedron: Asymmetry 15 2004 503
72. Y. Guo, and J.J. Grabowski Int. J. Mass Spectrom. Ion Proc. 97 1990 253
73. J. Hu, B.T. Hill, and R.R. Squires J. Am. Chem. Soc. 119 1997 11699
74. R.J. Schmitt, V.M. Bierbaum, and C.H. DePuy J. Am. Chem. Soc. 101 1979 6443
75. K.M. Broadus, and S.R. Kass J. Am. Chem. Soc. 123 2001 4189
76. C.D. Cleven, S.H. Hoke II, R.G. Cooks, D.A. Hrovat, J.M. Smith, M.-S. Lee, and W.T. Borden J. Am. Chem. Soc. 118 1996 10872