A comparison between theoretical and experimental models of electrophilicity and nucleophilicity

Journal of Molecular Structure: THEOCHEM

Volumn 896, Issue 1-3, 2009, Pages 73-79

  Chamorro, Eduardo ^a   Duque Noreña, Mario ^a   Pérez, Patricia ^a  

^a UNIVERSIDAD ANDRÉS BELLO   (Chile)

Author keywords

DFT; Electrophilicity; Nucleophilicity; Scales

Indexed keywords

EID: 58949103819     PISSN: 01661280     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.theochem.2008.11.009     Document Type: Article

References (111)

1. Ingold C.K. Chem. Rev. 15 (1934) 225
2. Baidya M., and Mayr H. Chem. Commun. (2008) 1792
3. Kempf B., Hampel N., Ofial A.R., and Mayr H. Chem. Eur. J. 9 (2003) 2209
4. Dilman A.D., Ioffe S.L., and Mayr H. J. Org. Chem. 66 (2001) 3196
5. Denegri B., Minegishi S., Kronja O., and Mayr H. Angew. Chem. Int. Ed. Engl. 43 (2004) 2302
6. Denegri B., Ofial A.R., Jurk S., Streiter A., Kronja O., and Mayr H. Chem. Eur. J. 12 (2006) 1657
7. Minegishi S., Kobayashi S., and Mayr H. J. Am. Chem. Soc. 126 (2004) 5174
8. Tishkov A.A., and Mayr H. Angew. Chem. Int. Ed. Engl. 44 (2005) 142
9. Tishkov A.A., Schmidhammer U., Roth S., Riedle E., and Mayr H. Angew. Chem. Int. Ed. Engl. 44 (2005) 4623
10. Schaller H.F., and Mayr H. Angew. Chem. Int. Ed. Engl. 47 (2008) 3958
11. Swain C.G., and Scott C.B. J. Am. Chem. Soc. 75 (1953) 141
12. Edwards J.O. J. Am. Chem. Soc. 76 (1954) 1540
13. Bunnett J.F. Ann. Rev. Phys. Chem. 14 (1963) 271
14. Pearson R.G., Sobel H., and Songstad J. J. Am. Chem. Soc 90 (1968) 319
15. Mayr H., Schneider R., and Grabis U. J. Am. Chem. Soc. 112 (1990) 4460
16. Mayr H., and Ofial A.R. Pure Appl. Chem. 77 (2005) 1807
17. Mayr H., Kuhn O., Gotta M.F., and Patz M. J. Phys. Org. Chem. 11 (1998) 642
18. Schaller H.F., Schmidhammer U., Riedle E., and Mayr H. Chem. Eur. J. 14 (2008) 3866
19. Nigst T.A., Westermaier M., Ofial A.R., and Mayr H. Eur. J. Org. Chem. (2008) 2369
20. Brotzel F., and Mayr H. Org. Biomol. Chem. 5 (2007) 3814
21. Phan T.B., Breugst M., and Mayr H. Angew. Chem. Int. Ed. Engl. 45 (2006) 3869
22. Lakhdar S., Westermaier M., Terrier F., Goumont R., Boubaker T., Ofial A.R., and Mayr H. J. Org. Chem. 71 (2006) 9088
23. Bug T., Hartnagel M., Schlierf C., and Mayr H. Chem. Eur. J. 9 (2003) 4068
24. Mayr H., and Minegishi S. Angew. Chem. Int. Ed. Engl. 41 (2002) 4493
25. Mayr H., and Ofial A.R. Tetrahedron Lett. 38 (1997) 3503
26. Roth M., and Mayr H. Angew. Chem. Int. Ed. Engl. 34 (1995) 2250
27. Mayr H., and Vonderbruggen U. Chem. Ber-Rec. 21 (1988) 339
28. Mayr H., Schneider R., and Grabis U. Angew. Chem. Int. Ed. Engl. 25 (1986) 1017
29. Ofial A.R., Ohkubo K., Fukuzumi S., Lucius R., and Mayr H. J. Am. Chem. Soc. 125 (2003) 10906
30. Minegishi S., and Mayr H. J. Am. Chem. Soc. 125 (2003) 286
31. Mayr H., Bug T., Gotta M.F., Hering N., Irrgang B., Janker B., Kempf B., Loos R., Ofial A.R., Remennikov G., and Schimmel H. J. Am. Chem. Soc. 123 (2001) 9500
32. Berger S.T.A., Seeliger F.H., Hofbauer F., and Mayr H. Org. Biomol. Chem. 5 (2007) 3020
33. Kempf B., and Mayr H. Chem. Eur. J. 11 (2005) 917
34. Brotzel F., Kempf B., Singer T., Zipse H., and Mayr H. Chem. Eur. J. 13 (2007) 336
35. Mayr H., Kempf B., and Ofial A.R. Acc. Chem. Res. 36 (2003) 66
36. Burfeindt J., Patz M., Muller M., and Mayr H. J. Am. Chem. Soc. 120 (1998) 3629
37. Mayr H., Hartnagel M., and Grimm K. Liebigs Ann-Rec. (1997) 55
38. Brotzel F., Chu Y.C., and Mayr H. J. Org. Chem. 72 (2007) 3679
39. Mayr H., and Rau D. Chem. Ber. 127 (1994) 2493
40. Mayr H., Kuhn O., Schlierf C., and Ofial A.R. Tetrahedron 56 (2000) 4219
41. Mayr H., and Patz M. Angew. Chem. Int. Ed. Engl. 33 (1994) 938
42. H. Mayr, 2008. Available from: .
43. Lucius R., Loos R., and Mayr H. Angew. Chem. Int. Ed. Engl. 41 (2002) 91
44. Parr R.G., and Yang W. Density Functional Theory of Atoms and Molecules (1989), Oxford University Press, Oxford
45. Geerlings P., De Proft F., and Langenaeker W. Chem. Rev. 103 (2003) 1793
46. Chermette H. J. Comput. Chem. 20 (1999) 129
47. Ayers P.W., and Parr R.G. J. Am. Chem. Soc. 123 (2001) 2007
48. Ayers P.W., and Parr R.G. J. Am. Chem. Soc. 122 (2000) 2010
49. Ayers P.W., Morrison R.C., and Roy R.K. J. Chem. Phys. 116 (2002) 8731
50. Ayers P.W., and Levy M. Theor. Chem. Acc. 103 (2000) 353
51. Ayers P.W., Anderson J.S.M., and Bartolotti L.J. Int. J. Quantum Chem. 101 (2005) 520
52. Ayers P.W. Theor. Chem. Acc. 106 (2001) 271
53. Ayers P.W. Faraday Discuss. 135 (2007) 161
54. Cohen M.H., and Wasserman A. J. Phys. Chem. A 111 (2007) 2229
55. Cohen M.H., and Wasserman A. J. Stat. Phys. 125 (2006) 1125
56. Parr R.G., Szentpaly L.v., and Liu S. J. Am. Chem. Soc. 121 (1999) 1922
57. Roy D.R., Pal N., Mitra A., Bultinck P., Parthasaranthi R., Subramanian V., and Chattaraj P.K. Eur. J. Med. Chem. 42 (2007) 1365
58. Padmanabhan J., Parthasarathi R., Elango M., Subramanian V., Krishnamoorthy B.S., Gutierrez-Oliva S., Toro-Labbe A., Roy D.R., and Chattaraj P.K. J. Phys. Chem. A 111 (2007) 9130
59. Padmanabhan J., Parthasarathi R., Subramanian V., and Chattaraj P.K. J. Phys. Chem. A 111 (2007) 1358
60. K. Gupta, D.R. Roy, V. Subramanian, P.K. Chattaraj, J. Mol. Struct. (THEOCHEM) 812 (2007) 13.
61. Chattaraj P.K., Roy D.R., Giri S., Mukherjee S., Subramanian V., Parthasarathi R., Bultinck P., and Van Damme S. J. Chem. Sci. 119 (2007) 475
62. Roy D.R., Sarkar U., Chattaraj P.K., Mitra A., Padmanabhan J., Parthasarathi R., Subramanian V., Van Damme S., and Bultinck P. Mol. Divers. 10 (2006) 119
63. Parthasarathi R., Padmanabhan J., Elango M., Chitra K., Subramanian V., and Chattaraj P.K. J. Phys. Chem. A 110 (2006) 6540
64. D.R. Roy, P. Bultinck, V. Subramanian, P.K. Chattaraj, J. Mol. Struct. (THEOCHEM) 854 (2008) 35.
65. Parthasarathi R., Subramanian V., Roy D.R., and Chattaraj P.K. Bioorg. Med. Chem. 12 (2004) 5533
66. Chattaraj P.K., Maiti B., and Sarkar U. J. Phys. Chem. A 107 (2003) 4973
67. Chamorro E., Chattaraj P.K., and Fuentealba P. J. Phys. Chem. A 107 (2003) 7068
68. Chattaraj P.K., Sarkar U., and Roy D.R. Chem. Rev. 106 (2006) 2065
69. Pérez P., Chamorro E., and Ayers P.W. J. Chem. Phys. 128 (2008)
70. Chamorro E., Pérez P., De Proft F., and Geerlings P. J. Chem. Phys. 124 (2006)
71. Chamorro E., Santos J.C., Escobar C.A., and Pérez P. Chem. Phys. Lett. 431 (2006) 210
72. Guerra D., Andrés J., Chamorro E., and Pérez P. Theor. Chem. Acc. 118 (2007) 325
73. Pinter B., De Proft F., Van Speybroeck V., Hemelsoet K., Waroquier M., Chamorro E., Veszpremi T., and Geerlings P. J. Org. Chem. 72 (2007) 348
74. Pinter B., De Proft F., Vezpremi T., and Geerlings P. J. Org. Chem. 73 (2008) 1243
75. Chamorro E., De Proft F., and Geerlings P. J. Chem. Phys. 123 (2005)
76. Cardenas C., Chamorro E., and Notario R. J. Phys. Chem. A 109 (2005) 4352
77. Pérez P., Toro-Labbe A., Aizman A., and Contreras R. J. Org. Chem. 67 (2002) 4747
78. Domingo L.R., Aurell M.J., Pérez P., and Contreras R. Tetrahedron 58 (2002) 4417
79. Domingo L.R., Aurell M.J., Pérez P., and Contreras R. J. Phys. Chem. A 106 (2002) 6871
80. Pérez P., Domingo L.R., Jose Aurell M., and Contreras R. Tetrahedron 59 (2003) 3117
81. Domingo L.R., Chamorro E., and Pérez P. J. Phys. Chem. A 112 (2008) 4046
82. Domingo L.R., Aurell M.J., Pérez P., and Contreras R. J. Org. Chem. 68 (2003) 3884
83. Pérez P. J. Phys. Chem. A 107 (2003) 522
84. Pérez P., Toro-Labbe A., and Contreras R. J. Am. Chem. Soc. 123 (2001) 5527
85. Roy R.K., Krishnamurti S., Geerlings P., and Pal S. J. Phys. Chem. A 102 (1998) 3746
86. Roy D.R., Parthasarathi R., Padmanabhan J., Sarkar U., Subramanian V., and Chattaraj P.K. J. Phys. Chem. A 110 (2006) 1084
87. C. Morell, A. Grand, S. Gutierrez-Oliva, A. Toro-Labbe, in: A. Toro-Labbe (Ed.), Theoretical Aspects of Chemical Reactivity, Elsevier B.V., Amsterdam, 2007, p. 125.
88. Morell C., Grand A., and Toro-Labbe A. Chem. Phys. Lett. 425 (2006) 342
89. Verstraelen T., Van Neck D., Ayers P.W., Van Speybroeck V., and Waroquier M. J. Chem. Theory Comput. 3 (2007) 1420
90. Morell C., Grand A., and Toro-Labbe A. J. Phys. Chem. A 109 (2005) 205
91. Cedillo A., Contreras R., Galvan M., Aizman A., Andres J., and Safont V.S. J. Phys. Chem. A 111 (2007) 2442
92. Anderson J.S.M., Melin J., and Ayers P.W. J. Chem. Theory Comput. 3 (2007) 358
93. Anderson J.S.M., Melin J., and Ayers P.W. J. Chem. Theory Comput. 3 (2007) 375
94. Anderson J.S.M., and Ayers P.W. Phys. Chem. Chem. Phys. 9 (2007) 2371
95. Ayers P.W., Morrison R.C., and Parr R.G. Mol. Phys. 103 (2005) 2061
96. De Vleeschouwer F., Van Speybroeck V., Waroquier M., Geerlings P., and De Proft F. Org. Lett. 9 (2007) 2721
97. Jaramillo P., Pérez P., Contreras R., Tiznado W., and Fuentealba P. J. Phys. Chem. A 110 (2006) 8181
98. Jaramillo P., Pérez P., and Fuentealba P. J. Phys. Org. Chem. 20 (2007) 1050
99. Jaramillo P., Domingo L.R., and Pérez P. Chem. Phys. Lett. 420 (2006) 95
100. Domingo L.R., Chamorro E., and Pérez P. J. Org. Chem. 73 (2008) 4615
101. Pérez P., Domingo L.R., Duque M., and Chamorro E. J. Mol. Struct. (THEOHEM) 895 (2009) 86
102. Gázquez J.L., Cedillo A., and Vela A. J. Phys. Chem. A 111 (2007) 1966
103. Yang W.T., Zhang Y.K., and Ayers P.W. Phys. Rev. Lett. 84 (2000) 5172
104. Perdew J.P., Parr R.G., Levy M., and Balduz Jr. J.L. Phys. Rev. Lett. 49 (1982) 1691
105. Ayers P.W. J. Math. Chem. 43 (2008) 285
106. Mayr H., and Ofial A.R. Angew. Chem. Int. Ed. Engl. 45 (2006) 1844
107. M.J. Frisch, G.W. Trucks, H.B. Schlegel, G.E. Scuseria, M.A. Robb, J.R. Cheeseman, J.A. Montgomery. Jr., T. Vreven, K.N. Kudin, J.C. Burant, J.M. Millam, S.S. Iyengar, J. Tomasi, V. Barone, B. Mennucci, M. Cossi, G. Scalmani, N. Rega, G.A. Petersson, H. Nakatsuji, M. Hada, M. Ehara, K. Toyota, R. Fukuda, J. Hasegawa, M. Ishida, T. Nakajima, Y. Honda, O. Kitao, H. Nakai, M. Klene, X. Li, J.E. Knox, H.P. Hratchian, J.B. Cross, V. Bakken, C. Adamo, J. Jaramillo, R. Gomperts, R.E. Stratmann, O. Yazyev, A.J. Austin, R. Cammi, C. Pomelli, J.W. Ochterski, P.Y. Ayala, K. Morokuma, G.A. Voth, P. Salvador, J.J. Dannenberg, V.G. Zakrzewski, S. Dapprich, A.D. Daniels, M.C. Strain, O. Farkas, D.K. Malick, A.D. Rabuck, K. Raghavachari, J.B. Foresman, J.V. Ortiz, Q. Cui, A.G. Baboul, S. Clifford, J. Cioslowski, B.B. Stefanov, G. Liu, A. Liashenko, P. Piskorz, I. Komaromi, R.L. Martin, D.J. Fox, T. Keith, M.A. Al-Laham, C.Y. Peng, A. Nanayakkara, M. Challacombe, P.M.W. Gill, B. Johnson, W. Chen, M.W. Wong, C. Gonzalez, J.A. Pople, Gaussian 03. Revision D. 01, Gaussian, Inc., Wallingford, CT, (2004).
108. Cohen A.J., Mori-Sanchez P., and Yang W.T. Phys. Rev. B 77 (2008)
109. Mori-Sanchez P., Cohen A.J., and Yang W.T. Phys. Rev. Lett. 100 (2008)
110. Ayers P.W., De Proft F., Borgoo A., and Geerlings P. J. Chem. Phys. 126 (2007)
111. Tumanov V.V., Tishkov A.A., and Mayr H. Angew. Chem. Int. Ed. Engl. 46 (2007) 3563