Thermochemistry and structures of solvated SN2 complexes and transition states in the gas phase: Experiment and theory

International Journal of Mass Spectrometry

Volumn 241, Issue 2-3 SPEC.ISS., 2005, Pages 205-223

  Bogdanov, B ^a   McMahon, T B ^a  

^a UNIVERSITY OF WATERLOO   (Canada)

Author keywords

Potential energy surfaces; SN2 reaction; Structure; Thermochemistry; Transition states

Indexed keywords

BROMINE DERIVATIVE; CHLORINE DERIVATIVE; SOLVENT; SULFUR DERIVATIVE;

ARTICLE; CALCULATION; CHEMICAL BINDING; CHEMICAL REACTION; CHEMICAL STRUCTURE; CHEMISTRY; COMPLEX FORMATION; CORRELATION ANALYSIS; DENSITY; ENERGY; ENTHALPY; ENTROPY; GAS; IONIZATION; MASS SPECTROMETRY; POLYMERIZATION; PRESSURE MEASUREMENT; ROTATION; SOLVATION; STRUCTURE ANALYSIS; THERMAL ANALYSIS; WATER TRANSPORT;

EID: 15944386350     PISSN: 13873806     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.ijms.2004.12.018     Document Type: Article

References (85)

1. C.K. Ingold Structure and Reactivity in Organic Chemistry 2nd ed. 1969 Cornell University Press Ithaca, NY and references cited therein
2. F. Aziz, and E.A. Moelwyn-Hughes J. Chem. Soc. 1959 2635
3. B.W. Marshall, and E.A. Moelwyn-Hughes J. Chem. Soc. 1959 2640
4. R.H. Bathgate, and E.A. Moelwyn-Hughes J. Chem. Soc. 1959 2642
5. R. Alexander, E.C.F. Ko, A.J. Parker, and T.J. Broxton J. Am. Chem. Soc. 90 1968 5049 and references cited therein.
6. A.J. Parker Chem. Rev. 69 1969 1 and references cited therein
7. S.R. Hartshorn Aliphatic Nucleophilic Substitution 1973 Cambridge University Press London
8. A. Streitweiser Jr. Solvolytic Displacement Reactions 1973 McGraw-Hill New York, NY
9. W.J. Albery, and M.M. Kreevoy Adv. Phys. Org. Chem. 16 1978 87 and references cited therein
10. N2 Mechanism 1992 Wiley New York, NY and references cited therein
11. D.K. Bohme, and G.I. Mackay J. Am. Chem. Soc. 103 1981 978
12. M. Henchman, J.F. Paulson, and P.M. Hierl J. Am. Chem. Soc. 105 1983 5509
13. M. Henchman, P.M. Hierl, and J.F. Paulson J. Am. Chem. Soc. 107 1985 2812
14. D.K. Bohme, and A.B. Raksit J. Am. Chem. Soc. 106 1984 3447
15. D.K. Bohme, and A.B. Raksit Can. J. Chem. 63 1985 3007
16. P.M. Hierl, A.F. Ahrens, M. Henchman, A.A. Viggiano, J.F. Paulson, and D.C. Clary J. Am. Chem. Soc. 108 1986 3142
17. P.M. Hierl, A.F. Ahrens, M. Henchman, A.A. Viggiano, and J.F. Paulson Int. J. Mass Spectrom. Ion Processes 81 1987 101
18. P.M. Hierl, A.F. Ahrens, M.J. Henchman, A.A. Viggiano, and J.F. Paulson Faraday Discuss. Chem. Soc. 85 1988 37
19. K. Giles, and E.P. Grimsrud J. Phys. Chem. 97 1993 1318
20. R.A.J. O'Hair, G.E. Davico, J. Hacaloglu, T.T. Dang, C.H. DePuy, and V.M. Bierbaum J. Am. Chem. Soc. 116 1994 3609
21. P.M. Hierl, J.F. Paulson, and M.J. Henchman J. Phys. Chem. 99 1995 15655
22. A.A. Viggiano, S.T. Arnold, R.A. Morris, A.F. Ahrens, and P.M. Hierl J. Phys. Chem. 100 1996 14397
23. S.L. Craig, and J.I. Brauman J. Am. Chem. Soc. 118 1996 6786
24. J.V. Seeley, R.A. Morris, and A.A. Viggiano J. Phys. Chem. A 101 1997 4598
25. J.V. Seeley, R.A. Morris, A.A. Viggiano, H. Wang, and W.L. Hase J. Am. Chem. Soc. 119 1997 577
26. S.L. Craig, and J.I. Brauman J. Am. Chem. Soc. 121 1999 6690
27. K. Morokuma J. Am. Chem. Soc. 104 1982 3732
28. W.-P. Hu, and D.G. Truhlar J. Am. Chem. Soc. 116 1994 7797
29. F.M. Bickelhaupt, E.J. Baerends, and N.M.M. Nibbering Chem. Eur. J. 2 1996 196
30. H. Tachikawa J. Phys. Chem. A 104 2000 497
31. H. Tachikawa J. Phys. Chem. A 105 2001 1260
32. S. Raugei, G. Cardini, and V. Schettino J. Chem. Phys. 114 2001 4089
33. A.A. Mohamed, and F. Jensen J. Phys. Chem. A 105 2001 3259
34. S.C. Tucker, and D.G. Truhlar J. Am. Chem. Soc. 112 1990 3347
35. X.G. Zhao, S.C. Tucker, and D.G. Truhlar J. Am. Chem. Soc. 113 1991 826
36. X.G. Zhao, D.-H. Lu, Y.-P. Liu, G.C. Lynch, and D.G. Truhlar J. Chem. Phys. 97 1992 6369
37. M. Re, and D. Laria J. Chem. Phys. 105 1996 4584
38. Y. Okuno J. Chem. Phys. 105 1996 5817
39. Y. Okuno J. Am. Chem. Soc. 122 2000 2925
40. J.E. Szulejko, J.J. Fisher, T.B. McMahon, and J. Wronka Int. J. Mass Spectrom. Ion Processes 83 1988 147
41. 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, M.W. Gill, B. Johnson, W. Chen, M.W. Wong, J.L. Andres, C. Gonzalez, M. Head-Gordon, E.S. Replogle, and J.A. Pople Gaussian 98 1998 Gaussian Inc Pittsburgh, PA Revision A.7
42. C.C.J. Roothan Rev. Mod. Phys. 23 1951 69
43. C. Møller, and M.S. Plesset Phys. Rev. 46 1934 618
44. W.J. Hehre, R. Ditchfield, and J.A. Pople J. Chem. Phys. 56 1972 2257
45. M.M. Francl, W.J. Petro, W.J. Hehre, J.S. Binkley, M.S. Gordon, D.J. DeFrees, and J.A. Pople J. Chem. Phys. 77 1982 3654
46. T. Clark, J. Chandrasekhar, and P.V.R. Schleyer J. Comp. Chem. 4 1983 294
47. R. Krishnam, J.S. Binkley, R. Seeger, and J.A. Pople J. Chem. Phys. 72 1980 650
48. P.M.W. Gill, B.G. Johnson, J.A. Pople, and M.J. Frisch Chem. Phys. Lett. 97 1992 499
49. A.P. Scott, and L. Radom J. Phys. Chem. 100 1996 16502
50. 2 versus experimental frequencies from reference 51.
51. T. Shimanouchi Tables of Molecular Vibrational Frequencies Consolidated Volume I 1972 National Bureau of Standards Washington, DC p. 1
52. M.J. Frisch, J.A. Pople, and J.S. Binkley J. Chem. Phys. 80 1984 3265
53. P.C. Hariharan, and J.A. Pople Theor. Chim. Acta 28 1973 213
54. P.J. Hay, and W.R. Wadt J. Chem. Phys. 82 1985 284
55. M.N. Glukhovtsev, A. Pross, M.P. McGrath, and L. Radom J. Chem. Phys. 103 1995 1878
56. L.A. Curtiss, K. Raghavachari, and J.A. Pople J. Chem. Phys. 94 1993 7221
57. Gaussian 98 User's Reference, second ed., Gaussian Inc., 1999.
58. J.B. Foresman, T.A. Keith, K.B. Wiberg, J. Snoonian, and M.J. Frisch J. Phys. Chem. 100 1996 16098
59. D.R. Lide CRC Handbook of Chemistry and Physics, Ref. Data 76th ed. 1995 Boca Raton, FL CRC
60. L. Deng, V. Branchadell, and T. Ziegler J. Am. Chem. Soc. 116 1994 10645 and references cited therein
61. M.N. Glukhovtsev, A. Pross, and L. Radom J. Am. Chem. Soc. 117 1995 2024 and references cited therein
62. M.N. Glukhovtsev, R.D. Bach, A. Pross, and L. Radom Chem. Phys. Lett. 260 1996 558
63. M.N. Glukhovtsev, A. Pross, and L. Radom J. Am. Chem. Soc. 118 1996 6273 and references cited therein
64. S. Parthiban, G. de Oliveira, and J.M.L. Martin J. Phys. Chem. A 105 2001 895 and references cited therein
65. C. Li, P. Ross, J.E. Szulejko, and T.B. McMahon J. Am. Chem. Soc. 118 1996 9360
66. http://webbook.nist.gov/chemistry/
67. B. Bogdanov, Ph.D. Thesis, University of Waterloo, 2001.
68. J. Chandrassekhar, S.F. Smith, and W.L. Jorgensen J. Am. Chem. Soc. 106 1984 3049
69. J. Chandrassekhar, S.F. Smith, and W.L. Jorgensen J. Am. Chem. Soc. 107 1985 154
70. J. Chandrassekhar, and W.L. Jorgensen J. Am. Chem. Soc. 107 1985 2974
71. B. Bogdanov, M. Peschke, D.S. Tonner, J.E. Szulejko, and T.B. McMahon Int. J. Mass Spectrom. 185-187 1999 707
72. K. Hiraoka, S. Mizuse, and S. Yamabe J. Phys. Chem. 92 1988 3943
73. D.H. Evans, R.G. Keesee, and A.W. Castleman Jr. J. Chem. Phys. 86 1987 2927
74. B. Bogdanov, H.J.S. Lee, and T.B. McMahon Int. J. Mass Spectrom. 210-211 2001 387
75. R.C. Dougherty, J. Dalton, and J.D. Roberts Org. Mass Spectrom. 8 1974 77
76. R.C. Dougherty, and J.D. Roberts Org. Mass Spectrom. 8 1974 81
77. S.E. Barlow, J.M. Van Doren, and V.M. Bierbaum J. Am. Chem. Soc. 110 1988 7240
78. S.C. Tucker, and D.G. Truhlar J. Am. Chem. Soc. 112 1990 3338
79. B.D. Wladkowski, and J.I. Brauman J. Phys. Chem. 97 1993 13158
80. S.T. Graul, and M.T. Bowers J. Am. Chem. Soc. 116 1994 3875
81. G. Caldwell, T.F. Magnera, and P. Kebarle J. Am. Chem. Soc. 106 1984 959
82. W.B. Knighton, J.A. Bognar, P.M. O'Connor, and E.P. Grimsrud J. Am. Chem. Soc. 115 1993 22079
83. W.-P. Hu, and D.G. Truhlar J. Am. Chem. Soc. 117 1995 10726
84. E.D. Hughes, C.K. Ingold, and J.D.H. Mackie J. Chem. Soc. 1954 3173
85. P.B.D. de la Mare J. Chem. Soc. 1954 3180