Analysis of the changes on the potential energy surface of Menshutkin reactions induced by external perturbations

Journal of Molecular Structure: THEOCHEM

Volumn 371, Issue 1-3 SPEC. ISS., 1996, Pages 171-183

  Fradera, X ^a   Amat, Ll ^a   Torrent, M ^a   Mestres, J ^a   Constans, P ^a   Besalu E ^a   Marti J ^a   Simon, S ^a   Lobato, M ^a   Oliva, J M ^a   Luis, J M ^a   Andres J L ^a   Sola M ^a   Carbo R ^a   Duran, M ^a  

^a UNIVERSITY OF GIRONA   (Spain)

Author keywords

Electron density redistributions; Menshutkin reaction; Quantum molecular similarity measures; Solvent effects; Uniform electric fields

Indexed keywords

EID: 84962339272     PISSN: 01661280     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0166-1280(96)04637-4     Document Type: Article

References (73)

1. N. Menshutkin, Z. Phys. Chem., 5 (1890) 589.
2. N. Menshutkin, Z. Phys. Chem., 6 (1890) 41.
3. J.-L.M. Abboud, R. Notario, J. Bertrán and M. Solà, Prog. Phys. Org. Chem., 19 (1993) 1.
4. (a) S. Glasstone, K.J. Laidler and H. Eyring, in The Theory of Rate Processes, McGraw-Hill, New York, 1941.
5. (b) W.F.K. Wynne-Jones and H. Eyring, J. Chem. Phys., 3 (1935) 493.
6. J.N. Brønsted, Chem. Rev., 5 (1928) 231.
7. L.P. Hammett, Chem. Rev., 17 (1935) 125.
8. (a) S. Hammond, J. Am. Chem. Soc., 77 (1955) 334.
9. (b) J.E. Leffler, Science, 117 (1953) 340.
10. E.R. Thorton, J. Am. Chem. Soc., 89 (1967) 2915.
11. J.C. Harris and J.L. Kurz, J. Am. Chem. Soc., 92 (1970) 349.
12. W.L. Hase, Science, 266 (1994) 998.
13. Y.F. Yen, R.J. Cross and M. Saunders, J. Am. Chem. Soc., 113 (1993) 5563.
14. E.M. Arnett and R. Reich, J. Am. Chem. Soc., 102 (1980) 5892.
15. J.M. Harris, M.S. Paley and T.W. Prasthofer, J. Am. Chem. Soc., 103 (1981) 5915.
16. U. Berg and R. Gallo, Acta Chem. Scand., B37 (1983) 661.
17. J.W. Viers, J.C. Schug, M.D. Stovall and J.I. Seeman, J. Comput. Chem. 5 (1984) 598.
18. M. Solà, A. Lledós, M. Duran, J. Bertrán and J.-L.M. Abboud, J. Am. Chem. Soc., 113 (1991) 2873.
19. J. Gao, J. Am. Chem. Soc., 113 (1991) 7796.
20. (a) J. Gao and X. Xia, J. Am. Chem. Soc., 115 (1993) 9667.
21. (b) J. Gao and X. Xia, in C.J. Cramer and D.G. Truhlar (Eds.), Structure and Reactivity in Aqueous Solution, ACS Symp. Ser. 568, Washington, DC, 1994.
22. U. Maran, T.A. Pakkanen and M. Karelson, J. Chem. Soc., Perkin Trans. 2, (1994) 2445.
23. S. Shaik, A. Ioffe, A.C. Reddy and A. Pross, J. Am. Chem. Soc., 116 (1994) 262.
24. U. Berg, M. Chanon, R. Gallo and M. Rajzmann, J. Org. Chem., 60 (1995) 1975.
25. S.S. Shaik, Prog. Phys. Org. Chem., 15 (1985) 197.
26. (a) J. Bertrán, in J. Bertrán and I.G. Csizmadia (Eds.), New Theoretical Concepts for Understanding Organic Reactions, Kluwer, Dordrecht, 1989, pp. 231-255.
27. (b) J. Bertrán, J.M. Lluch, A. González-Lafont, V. Dillet and V. Pérez, Am. Chem. Soc. Symp. Ser., 568 (1994) 168.
28. (c) M. Solà, E. Carbonell, A. Lledós, M. Duran and J. Bertrán, J. Mol. Struct. (Theochem), 255 (1992) 283.
29. (d) J.L. Andrés, A. Lledós, M. Duran and J. Bertrán, Chem. Phys. Lett., 153 (1988) 82.
30. (e) E. Carbonell, J.L. Andrés, A. Lledós, M. Duran and J. Bertrán, J. Am. Chem. Soc., 110 (1988) 996.
31. (f) M. Duran and J. Bertrán, Rep. Mol. Theory, 1 (1990) 57.
32. (g) M. Solà, A. Lledós, M. Duran and J. Bertrán, J. Am. Chem. Soc., 114 (1992) 869.
33. (h) M. Solà, A. Lledós, M. Duran and J. Bertrán, Int. J. Quantum Chem., 40 (1991) 511.
34. (i) M. Solà, J.L. Andrés, M. Duran, A. Lledós and J. Bertrán, Theor. Chim. Acta, 91 (1995) 333.
35. (j) J.L. Andrés, A. Lledós and J. Bertrán, Chem. Phys. Lett., 223 (1994) 23.
36. (k) J.L. Andrés, M. Duran, A. Lledós and J. Bertrán, Chem. Phys. Lett., 124 (1986) 177.
37. J.G. Kirkwood, J. Chem. Phys. 2 (1934) 351.
38. M.H. Abraham and P.J. Grelliér, J. Chem. Soc., Perkin Trans. 2, (1976) 1735.
39. D.N. Kevill, J. Chem. Soc., Chem. Commun., (1981) 421.
40. M. Solà, J. Mestres, R. Carbó and M. Duran, J. Am. Chem. Soc., 116 (1994) 5909.
41. (a) R. Carbó, M. Arnau and L. Leyda, Int. J. Quantum Chem., 17 (1980) 1185.
42. (b) R. Carbó and B. Calabuig, Int. J. Quantum Chem., 42 (1992) 1681.
43. (a) R. Carbó, B. Calabuig, L. Vera and E. Besalú, Adv. Quantum Chem., 25 (1994) 253.
44. (b) E. Besalú, R. Carbó, J. Mestres and M. Solà, in Molecular Similarity. Topics in Current Chemistry Series, Springer, Vol. 173, Berlin, 1995, pp. 31-62.
45. (c)R. Carbó and E. Besalú, in R. Carbó (Ed.), Molecular Similarity and Reactivity: From Quantum Chemistry to Phenomenological Approaches, Kluwer, Dordrecht, 1995, pp. 3-30.
46. R. Carbó and Ll. Domingo, Int. J. Quantum Chem., 32 (1987) 517.
47. (a) M. Solà, J. Mestres, M. Duran and R. Carbó, J. Chem. Inf. Comput. Sci., 34 (1994) 1047.
48. (b) J. Mestres, M. Solà, M. Duran and R. Carbó, J. Comp. Chem., 15 (1994) 1113.
49. (c)J. Mestres, M. Solà, M. Duran and R. Carbó, in R. Carbó (Ed.), Molecular Similarity and Reactivity: From Quantum Chemistry to Phenomenological Approaches, Kluwer, Dordrecht, 1995, pp. 89-111.
50. (d)M. Solà, J. Mestres, R. Carbó and M. Duran, J. Chem. Phys., 104 (1996) 636.
51. J. Mestres, M. Solà, R. Carbó, F.J. Luque and M. Orozco, J. Phys. Chem., 100 (1996) 606.
52. (a) J. Wang, L.A. Eriksson, R.J. Boyd, Z. Shi and B.G. Johnson, J. Phys. Chem., 98 (1994) 1844.
53. (b) J. Wang, Z. Shi, R.J. Boyd and C.A. Gonzalez, J. Phys. Chem., 98 (1994) 6988.
54. (c) M. Solà, J. Mestres, R. Carbó and M. Duran, in F. Sanz, J. Giraldo and F. Manaut (Eds.), QSAR and Molecular Modelling: Concepts, Computational Tools and Biological Applications, Prous Science, Barcelona, 1995, pp. 403-406.
55. (a) R.F.W. Bader, Acc. Chem. Res., 18 (1985) 9.
56. (b) R.F.W. Bader, in Atoms in Molecules: A Quantum Theory, Clarendon Press, Oxford, 1990.
57. (a) J.S. Binkley, J.A. Pople and W.J. Hehre, J. Am. Chem. Soc., 102 (1980) 939.
58. (b) G.W. Spitznagel, T. Clark, P.v.R. Schleyer and W.J. Hehre, J. Comput. Chem., 8 (1987) 1109.
59. (c)W.J. Pietro, M.M. Francl, W.J. Hehre, D.J. DeFrees, J.A. Pople and J.S. Binkley, J. Am. Chem. Soc., 104 (1982) 5039.
60. (a) S. Miertuš, E. Scrocco and J. Tomasi, Chem. Phys., 55 (1981) 117.
61. (b) J. Tomasi and M. Persico, Chem. Rev., 94 (1994) 2027.
62. J. Cioslowski, J. Am. Chem. Soc., 113 (1993) 6756.
63. M. Solà, J. Mestres, J.M. Oliva, M. Duran and R. Carbó, Int. J. Quantum Chem., 58 (1996) 361.
64. M.J. Frisch, G.W. Trucks, H.B. Schlegel, P.M.W. Gill, B.G. Johnson, M.A. Robb, J.R. Cheeseman, T.A. 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.J.P. Stewart, M. Head-Gordon, C. Gonzalez and J.A. Pople, GAUSSIAN 94, Rev. A.1, Gaussian, Inc., Pittsburgh, PA, 1995.
65. M.W. Schmidt, K.K. Baldridge, J.A. Boatz, S.T. Elbert, M.S. Gordon, J.J. Jensen, S. Koseki, M. Matsunaga, K.A. Nguyen, S. Su, T.L. Windus, M. Dupuis, J.A. Montgomery, J. Comput. Chem., 14 (1993) 1347.
66. D.G. Truhlar and M.S. Gordon, Science, 249 (1990) 491.
67. P. Constans and R. Carbó, J. Chem. Inf. Comput. Sci., 35 (1995) 1046.
68. P. Constans and R. Carbó, ASA Calculations, Institut de Quimica Computacional, Universitat de Girona, Girona, CAT, 1995.
69. J. Mestres, Electra, Institut de Química Computacional, Universitat de Girona, Girona, CAT, 1994.
70. (a) K. Okamoto, S. Fukui and H. Shingu, Bull. Chem. Soc. Jpn, 40 (1967) 1920.
71. (b) K. Okamoto, S. Fukui, I. Nitta and H. Shingu, Bull. Chem. Soc. Jpn, 40 (1967) 2354.
72. L. Pauling, J. Am. Chem. Soc., 69 (1947) 542.
73. R.G. Pearson, Acc. Chem. Res., 26 (1993) 250.