A systematic study of the ancillary effect of different molecules on the acetonitrile hydrolysis

Journal of Molecular Structure: THEOCHEM

Volumn 497, Issue 1-3, 2000, Pages 173-188

  Barbosa, L A M M ^a   Van Santen, R A ^a  

^a EINDHOVEN UNIVERSITY OF TECHNOLOGY   (Netherlands)

Author keywords

Ab initio; Acetonitrile; Ancillary effect; Transition state; Water

Indexed keywords

ACETONITRILE;

ARTICLE; CALCULATION; CATALYSIS; CHEMICAL ANALYSIS; CHEMICAL REACTION; ENERGY; GEOMETRY; HYDRATION; HYDROLYSIS; ISOMERISM; MOLECULE; QUANTUM CHEMISTRY;

EID: 0034143242     PISSN: 01661280     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0166-1280(99)00283-3     Document Type: Article

References (80)

1. F.C Schalfer H Rappoport The Chemistry of the Cyano Group 1970 Interscience New York chap. 6
2. M.C Sze A.P Gelbein R.T Whitehead Hydro. Proc. September 1973 209
3. M.C Sze A.P Gelbein Hydro. Proc. 55 1976 103
4. Y Ashina M Suto A Tanaka T Tosa T Kobayashi Industrial Application of Immobilized Biocatalysis 1992 Marcel Dekker New York chap. 7
5. V.K Krieble J.G McNally J. Am. Chem. Soc. 51 1929 3369
6. V.K Krieble C.I Noll J. Am. Chem. Soc. 61 1939 561
7. B.S Rabinovitch C.A Winkler A.R.P Stewart Can. J. Res. 20 7 1942 121
8. B.S Rabinovitch C.A Winkler Can. J. Res. 20 7 1942 186
9. K Sugiyama H Miura Y Nakano H Suzuki T Matsuda Bull. Chem. Soc. Jpn 60 1987 453
10. C.P Wilgus S Downing E Molitor S Bains R.M Pagni G.W Kaballa Tetrahedron Lett. 36 20 1995 3469
11. M Lasperas P Graffin P.J Geneste J. Catal. 139 1993 362
12. J.F Haw M.B Hall A.E Alvarado-Swaisgood E.J Munson Z Lin L.W Beck T Howard J. Am. Chem. Soc. 116 1994 7308
13. B Izzo C.L Harrell M.T Klein AIChE J. 43 8 1997 2049
14. N.V Kaminskaia N.M Kostié J. Chem. Soc. Dalton Trans. 1996 3677
15. M.A Cohen J.S Parrat N Turner Tetrahedron: Asymmetry 312 1992 1543
16. M.A Cohen J Sawden N Turner Tetrahedron Lett. 49 1990 7223
17. T Berad M.A Cohen J.S Parrat N Turner Tetrahedron: Asymmetry 4 6 1993 1085
18. J Crosby J Moilliet J.S Parrat N Turner J. Chem. Soc. Perkins Trans. 1 1994 1679
19. O.M Cohn M.X Wang J. Chem. Soc. Perkin Trans. 1 1997 1099
20. K Matoishi A Sano N Imai T Yamzaki M Yokoyama T Sugai H Ohta Tetrahedron: Asymmetry 9 1998 1097
21. Y Izumi Catal. Today 33 1997 371
22. R.A van Santen J.W Niemantsverdriet M.V Twigg M.S Spencer Chemical Kinetics and Catalysis 1995 Plenum Press New York
23. A.J Chalk L Radom J. Am. Chem. Soc. 119 1997 7573
24. R Cárdenas J Lagúnez-Otero A Flores-Rivero Int. J. Quant. Chem. 68 1998 253
25. J.P Guthrie J. Am. Chem. Soc. 118 1996 12 886
26. D Lu G.A Voth J. Am. Chem. Soc. 120 1998 4006
27. R.A Cox J. Chem. Soc. Perkin Trans. 2 1997 1743
28. E Humeres L.F Sequinel M Nunes C.M.S Oliveira P.J Barrie Can. J. Chem. 76 1998 960
29. R.A Cox Can. J. Chem. 75 1997 1093
30. H Slebocka-Tilk C.G Rescorla S Shirim A.J Bennet R.S Brown J. Am. Chem. Soc. 119 1997 10 969
31. T.H Fife R Bembi R Natarajan J. Am. Chem. Soc. 118 1996 12 956
32. G Raspoet M.T Nguyen M McGarraghy A.F Hegarty J. Org. Chem. 63 1998 6867
33. R.M Smith D.E Hansen J. Am. Chem. Soc. 120 1998 8910
34. M Lewis R Glaser J. Am. Chem. Soc. 120 1998 8541
35. R.H DeWolfe F.B Augustine J. Org. Chem. 30 1965 699
36. S Wolfe C.K Kim K Yang Can. J. Chem. 72 1994 1033
37. R.A Cox Can. J. Chem. 76 1998 2146
38. J Pitarch M.F Ruiz-López E Silla J.-L Pauscual-Ahuir I Tuñón J. Am. Chem. Soc. 120 1998 2146
39. J.F Haw T Xu J.B Nicholas P.W Goguen Nature 389 1997 833
40. S.R Blaszkowski R.A van Santen J. Phys. Chem. 101 1997 2292
41. P.E Sinclair C.R.A Catlow J. Chem. Soc. Faraday Trans. 92 1996 2099
42. K.D Bohme G.I Mackay J. Am. Chem. Soc. 103 1981 978
43. M.L Chabinyc S.L Craig C.K Regan J.I Brauman Science 279 1998 1882
44. K Morokuna J. Am. Chem. Soc. 104 1982 3732
45. T.H Dunning Jr. P.J Hay H.F Schaefer III Modern Theoretical Chemistry 1976 Plenum Press New York chap. 1
46. A.C Scheiner J Baker J.W Andzelm J. Comput. Chem. 18 1997 775
47. J Sauer G Pacchioni P.S Bagus F Parmigiani Cluster Models for Surface and Bulk Phenomena Proceedings of NATO Advanced Research Workshop, Italy 1992 Plenum Press New York
48. J.B Nicholas Topics Catal. 4 1997 157
49. W Koch R.H Hertwig Chem. Phys. Lett. 4 1997 157
50. L.A Curtiss K Raghavachari P.C Redfern J.A Pople Chem. Phys. Lett. 270 1997 419
51. M.J. Frisch, G.W. Trucks, H.B. Schlegel, P.M.W. Gill, B.G. Johnson, M.A. Robb, J.R. Cheeseman, T. Keith, G.A. Petersson, J.A. Montgomery, K. Raghavachari, M.A. Al-Laham, V.G. Zakrzewski, J.V. Ortiz, J.B. Foresman, J. Cioslowski, B.B. Stefanov, A. Nanayakkara, M. Challacombe, C.Y. Peng, P.Y. Ayala, W. Chen, M.W. Wong, J.L. Andres, E.S. Replogle, R. Gomperts, R.L. Martin, D.J. Fox, J.S. Binkley, D.J. Defrees, J. Baker, J.P. Stewart, M. Head-Gordon, C. Gonzalez, J.A. Pople, Gaussian 94, Revision E.2, Gaussian Inc., Pittsburgh, PA, 1995.
52. M.J. Frisch, G.W. Trucks, H.B. Schlegel, P.M.W. Gill, B.G. Johnson, M.W. Wong, J.B. Foresman, M.A. Robb, M. Head-Gordon, E.S. Replogle, R. Gomperts, J.L. Andres, K. Raghavachari, J.S. Binkley, C. Gonzalez, R.L. Martin, D.J. Fox, D.J. Defrees, J. Baker, J.J.P. Stewart, J.A. Pople, Gaussian 92/DFT, Revision G.4, Gaussian Inc., Pittsburgh, PA, 1993.
53. M.J Frish A Frish J.B Foresman Gaussian 94 User's Reference 1995 Gaussian, Inc Pittsburgh, PA
54. H.B Schlegel I Prigogine S.A Rice Advances in Chemical Physics AB INITIO Methods in Quantum Chemistry, Part I LXVII 1987 Wiley-Interscience Chichester, UK 249
55. F.B van Duijneveldt J.G.C.M van Duijneveldt-van de Rijdt J.H van Lenthe Chem. Rev. 94 1994 1878
56. G Lendvay I Mayer Chem. Phys. Lett. 297 1998 365
57. B Paizs S Suhai J. Comput. Chem. 19 6 1998 575
58. G.J Halász Á Vibók I Mayer J. Comput. Chem. 20 2 1999 274
59. J Pitarch M.F Ruiz-López E Silla J.-L Pauscual-Ahuir I Tuñón J. Phys. Chem. B 101 1997 3581
60. V.B Kazansky R.A van Santen Catal. Lett. 38 1996 115
61. D.A Zhurko M.V Frash V.B Kazansky Catal. Lett. 55 1998 7
62. W Hehre L Radom P.v.R Schleyer J.A Pople Ab-initio Molecular Orbital Theory 1986 Wiley-Interscience New York chap. 6
63. B.D Wladkowski S.A Chenoweth J.N Sanders M Krauss W.J Stevens J. Am. Chem. Soc. 119 1997 6423
64. J.D Gale Topics Catal. 3 1996 169
65. T Ziegler Chem. Rev. 91 1991 651
66. E.M Evleth E Kassab H Jessri L Montero L.R Sierra J. Phys. Chem. 100 1996 11 368
67. J.A Rupley G Careri Advances in Protein Chemistry 1991 Academic Press London 112
68. Y Jeanvoine J.G Ágyán G Kresse J Hafner J. Phys. Chem. B 102 1998 7307
69. J.B Foresman T.A Keith K.B Wiberg J Snoonian M.J Frisch J. Phys. Chem. 100 1996 16 098
70. K.B Wiberg J Ochterski A Streitwieser J. Am. Chem. Soc. 118 1996 8291
71. F.-T Luo A Jeevanandam Tetrahedron Lett. 39 1998 9455
72. G.A Russel P Chen J. Phys. Org. Chem. 11 1998 715
73. P Pérez R Contreras A Aizman J. Phys. Chem. 100 1996 19 326
74. N Agmon J. Phys. Chem. A 102 1998 192
75. O.N Ventura J.B Rama L Turi J.J Dannenberg J. Phys. Chem. 99 1995 131
76. R.J Kurland E.B Wilson J. Chem. Phys. 27 1957 585
77. E Hirota R Sugisaki C.J Vielsen O Sorensen J. Mol. Spectrosc. 49 1974 251
78. D.H Wu J.J Ho J. Phys. Chem. 102 1998 3582
79. S.J Cho C.C.J.Y Lee J.K Park S.B Suh J Park B.H Kim K.S Kim J. Org. Chem. 62 1997 4068
80. B Capon B.Z Guo F.C Kwok A.K Siddhanta C Zucco Acc. Chem. Res. 21 4 1988 135