Chemical reactivity as described by quantum chemical methods

International Journal of Molecular Sciences

Volumn 3, Issue 4, 2002, Pages 276-309

  Geerlings, P ^a   De Proft, F ^a  

^a VRIJE UNIVERSITEIT BRUSSEL   (Belgium)

Author keywords

Conceptual DFT; Organic Reactivity; Quantum Biochemistry; Quantum Similarity; Zeolites

Indexed keywords

FUNCTIONAL GROUP; SUBTILISIN; ZEOLITE;

AB INITIO CALCULATION; ACIDITY; ALKALINITY; CATALYSIS; CHEMICAL REACTION; DENSITY FUNCTIONAL THEORY; DIELS ALDER REACTION; ELECTRON TRANSPORT; ENZYME ACTIVITY; GAS; KINETICS; MOLECULAR MODEL; ORGANIC CHEMISTRY; QUANTUM CHEMISTRY; REVIEW; SUBSTITUTION REACTION; THERMODYNAMICS;

BETULACEAE;

EID: 0013165839     PISSN: 14220067     EISSN: None     Source Type: Journal    
DOI: 10.3390/i3040276     Document Type: Review

References (130)

1. Dirac, P.A.M. Proc. Roy.Soc.(London), 1929,123, 714.
2. Heitler, W.; London, F. Z. Phys. 1927,44, 455.
3. Pauling, L. The Nature of the Chemical Bond, Third Edition, Cornell University Press, Ithaca, 1960.
4. For a classic and authoritative account of Hückel's approach and its applications see A. Streitwieser, A. Molecular Orbital Theory for Organic Chemistry; John Wiley, 1961.
5. Mc Weeny, R. Coulson's Valence; Third Edition, Oxford, 1979.
6. (a) Hund, F. Z. Phys., 1928, 51, 759.
7. (b) Mulliken, R. S. Phys Rev., 1928, 32, 186.
8. Roothaan, C. C. J. Rev. Mod. Phys., 1951, 23, 69.
9. (a) For an overview see Hartree, D.R. The Calculation of Atomic Structures, John Wiley, New York, 1957.
10. (b) Hehre, W. J.; Radom, L.; Schleyer, P. v. R.; Pople, J. A. Ab Initio Molecular Orbital Theory, Wiley, New York, 1986.
11. Møller, C.; Plesset, M.S. Phys. Rev. 1934, 46, 618.
12. Shavitt, I. The Method of Configuration Interaction in Modern Theoretical Chemistry, Vol. 3, Methods of Electronic Structure Theory, H.F.Schaefer III Editor, Plenum Press, New York, 1977, p. 189.
13. Bartlett, R.J. J. Phys. Chem., 1989, 93, 1697.
14. Pople, J.A., et al., GAUSSIAN 98, 1998, and previous releases (GAUSSIAN 94, GAUSSIAN 92, ..., GAUSSIAN 70), Gaussian Inc., Pittsburgh A.
15. The Encyclopedia of Computational Chemistry, Schleyer P. v. Rague; Allinger, N. L.; Clark, T.; Gasteiger, J.; Kollman, P. A.; Schaefer, H. F.; Schreiner, P. R. (Eds.), John Wiley & Sons Ltd., Chichester 1998.
16. Pople, J.A. J. Chem. Phys., 1966, 43, S229.
17. Hohenberg, P.; Kohn, W. Phys. Rev. B, 1964, 136, 864.
18. Mc Weeny, R.; Sutcliffe, B.T. Methods of Molecular Quantum Mechanics, Academic Press, London, 1969, Chapter 4.
19. Kohn W.; Sham, L. Phys. Rev. A, 1965, 140, 1133.
20. Parr, R.G.; Yang, W. Ann. Rev. Phys. Chem., 1995, 46, 701.
21. (a)Becke, A.D. J. Chem. Phys, 1993, 98, 5648.
22. (b) Lee, C.; Yang, W.; Parr, R.G. Phys. Rev. B, 1998, 37, 785.
23. Geerlings, P.; De Proft, F.; Langenaeker, W. Adv. Quantum Chem., 1999, 33, 303.
24. Kohn, W.; Becke, A.; Parr, R.G. J. Phys. Chem., 1996, 100, 12974.
25. Koch, W.; Holthausen, M.C. "A Chemistry's Guide to Density Functional Theory", Wiley-VCH, Weinheim, 2000.
26. Parr, R.G. in "Density Functional Methods in Physics", Dreizler R.M.; da Providencia, J., Editors, Plenum, 1985, p. 141.
27. England, W.; Salmon, L.S.; Rüdenberg, K. Fortschr. Chem. Forsch., 1971, 23, 3 and references therein
28. Foster, M.; Boys, S.F. Rev. Mod. Phys. 1960, 32, 300.
29. Schaftenaar, G.; Noordik, J.H. "Molden: a pre- and post-processing program for molecular and electronic structures", J. Comp.-Aided Mol. Design, 2000, 14, 123.
30. Müller, N.; Pritchard, D.E. J. Chem. Phys., 1959, 31, 768.
31. Figeys, H. P.; Geerlings, P.; Raeymaekers, P.; Van Lommen, G.; Defay, N.; Tetrahedron, 1975, 31, 1731.
32. Parr, R.G.; Yang, W. Density Functional Theory of Atoms and Molecules, Oxford, 1989, Chapter
33. Parr, R.G.; Donelly, R.A.; Levy, M.; Palke, W.E. J. Chem. Phys., 1978, 68, 3801.
34. Iczkowski, R.P.; Margrave, J.L. J. Am. Chem. Soc. 1961, 83, 3547.
35. Mulliken, R.S. J. Chem. Phys., 1934, 2, 782.
36. For a series of papers covering various aspects of electronegativity see: Structure and Bonding, Vol. 66, Sen, K.D.; Jørgensen, C.K., Editors, Springer Verlag, Berlin, 1987.
37. Nalewajski, R.F.; Parr, R.G. J. Chem. Phys. 1982, 77, 399.
38. Parr, R.G.; Pearson, R.G. J. Am. Chem. Soc., 1983, 105, 7512.
39. Parr, R.G.; Yang, W. J. Am. Chem. Soc., 1984, 106, 4049.
40. Fukui, K.; Yonezawa, T.; Shinghu, H. J. Chem. Phys. 1952, 20, 722.
41. Yang, W.; Parr, R.G. Proc. Natl. Acad. Sci., 1985, 82, 6723.
42. Chermette, H. J. Comp. Chem., 1999, 20,129.
43. a) De Proft, F.; Geerlings, P. Chem. Rev., 2001, 101, 1451.
44. Geerlings, P.; De Proft, F.; Langenaeker, W. Chem. Rev., submitted.
45. Sanderson, R.T. Science, 1955, 121, 207.
46. Sanderson, R.T. Polar Covalence, Academic Press, New York, 1983.
47. Pearson, R.G. J. Am. Chem. Soc., 1963, 85, 3533.
48. Pearson, R.G. Chemical Hardness, J. Wiley, New York, 1997.
49. Chattaraj, P.K.; Lee, P.K.; Parr, R.G. J. Am. Chem. Soc., 1991, 113, 1855.
50. Parr, R.G.; Chattaraj, P.K. J. Am. Chem. Soc., 1991, 113, 1854.
51. De Proft, F.; Martin, J.M.L.; Geerlings, P. Chem. Phys. Lett., 1996, 250, 393; 1996, 256, 400.
52. De Proft, F.; Martin, J.M.L.; Geerlings, P. Chem. Phys. Lett., 1996, 250, 393; 1996, 256, 400.
53. De Proft, F.; Geerlings, P. J. Chem. Phys., 1997, 106, 3270.
54. De Oliveira, G.; Martin, J.M.L.; De Proft, F.; Geerlings, P. Phys. Rev., 1999, A60, 1034.
55. See for example the impressive series The Chemistry of Functional Groups, Patai, S. Editor, Interscience Publishers, London.
56. De Proft, F.; Langenaeker, W.; Geerlings, P. J. Phys. Chem., 1993, 97, 1826.
57. Datta, D.; Nabakishwar, S.S. J. Phys. Chem., 1990, 94, 2184.
58. Wray, V.; Ernst, L.; Luna, T.; Jakobsen, H.-J. J. Magn. Res., 1980, 40, 55.
59. Pearson, R.G. J. Am. Chem. Soc., 1998, 110, 7684.
60. De Proft, F.; Langenaeker, W.; Geerlings, P. Tetrahedron, 1995, 55, 4021.
61. Lias, S.G.; Bartmess, J.-E.; Liebman, J.F.; Holmes, J.L.; Levin, R.D.; Mallard, W.G. J. Phys. Chem. Ref. Data, 1988, 17 (Suppl 1).
62. Bartmess, J.E.; Scott, J.A.; Mc Iver Jr., R.T. J. Am. Chem. Soc., 1979, 101, 6056.
63. Taylor, R. Electrophilic Aromatic Substitution, J. Wiley, New York, 1990.
64. Vanermen, G.; Toppet, S.; Van Beylen, M.; Geerlings, P. J. Chem. Soc., Perkin Transactions 2, 1986, 699.
65. Wiberg, K.; Keith, T.A.; Frisch, M.J.; Muacko, M.; J. Phys. Chem., 1995, 99, 9072.
66. Safi, B.; Choho, K.; De Proft, F.; Geerlings P. J. Phys. Chem., 1998, A102, 5253.
67. Isaacs, N. Physical Organic Chemistry, Longman Scientific and Technical, Singapore, 1995.
68. Shaik, S.S.; Schlegel, H.B.; Wolfe, S. Theoretical Aspect of Physical Organic Chemistry, John Wiley, 1992.
69. Safi, B.; Choho, K.; Geerlings, P. J. Phys. Chem., 2001, A105, 591.
70. Gazquez, J.L. J. Phys. Chem., 1997, A101, 8967.
71. Politzer, P. J. Chem. Phys., 1987, 86, 1072.
72. Chandra, A. K.; Uchimaru, T. J. Phys. Chem. A, 2001, 105, 3578.
73. (a) Gazquez, J.L.; Mendez, F. J. Phys. Chem., 1994, 98, 459.
74. (b) Damoun, S.; Van de Woude, G.; Mendez, F.; Geerlings, P. J. Phys. Chem., 1997, A101, 886.
75. Geerlings, P.; De Proft, F. Int. J. Quant. Chem., 2000, 80, 227.
76. Eisenstein, O.; Lefour, J.M.; Anh, N.T.; Hudson, R.F. Tetrahedron, 1977, 33, 523.
77. K.N. Houk, K.N.; Li, Y.; Evanseck., J.T. Angew. Chem. Int. Ed. Engl., 1992, 31, 682.
78. Chandra, A. K.; Nguyen, M. T. J. Chem. Soc. Perkin Trans. 2, 1997, 1415.
79. (a) Raspoet, G.; Nguyen, M. T.; McGarraghy, M.; Hegarty, A. F. J. Org. Chem., 1998, 63, 6867.
80. (b) Nguyen, M. T.; Raspoet, G. Can. J. Chem. 1999, 77, 817.
81. (c) Nguyen, M. T.; Raspoet, G.; Vanquickenborne, L. G. J. Phys. Org. Chem., 2000, 13, 46.
82. (a) Chandra, A. K.; Geerlings, P.; Nguyen, M. T. J. Org. Chem., 1997, 62, 6417.
83. (b) Nguyen, L. T.; Le, T. N.; De Proft, F.; Chandra, A. K.; Langenaeker, W.; Nguyen, M. T.; Geerlings, P. J. Am. Chem. Soc., 1999, 121, 5992.
84. (a) Chandra, A. K.; Nguyen, M. T. J. Comput. Chem., 1998, 19, 195.
85. (b) Nguyen, L. T.; De Proft, F.; Chandra, A. K.; Uchimaru, T.; Nguyen, M. T.; Geerlings, P. J. Org. Chem. 2001, 66, 6096.
86. (c) Le, T. N.; Nguyen, L. T.; Chandra, A. K.; De Proft, F.; Geerlings, P.; Nguyen, M. T. J. Chem. Soc. Perkin Trans. 2 1999, 1249.
87. (d) Chandra, A. K.; Uchimaru, T.; Nguyen, M. T. J. Chem. Soc. Perkin Trans. 2 1999, 2117.
88. (e) Chandra, A. K.; Nguyen, M. T. J. Phys. Chem. A 1998, 102, 6181.
89. Sengupta, D.; Chandra, A. K.; Nguyen, M. T. J. Org. Chem. 1997, 62, 6404.
90. Ponti, A. J. Phys. Chem. A 2000, 104, 8843.
91. Rouvray, D.H. Top. Curr. Chem., 1995, 173, 2.
92. Mishra, P.C.; Kumar, A. Theor. Comput. Chem., 1996, 3, 257.
93. Carbo, M.; Arnau, M.; Leyda, L. Int. J. Quant. Chem., 1980, 17, 1185.
94. Parr, R.G.; Bartolotti, L.J. J. Phys. Chem., 1983, 87, 2810.
95. a) Boon, G.; De Proft, F.; Langenaeker, W.; Geerlings, P. Chem. Phys. Lett., 1996, 295, 122.
96. b) Boon, G.; Langenaeker, W.; De Proft, F.; De Winter, H.; Tollenaere, J.P.; Geerlings, P. J. Phys. Chem. A, 2001, 105, 8805.
97. Spatola, A.F. in Chemistry and Biochemistry of Amino Acids, Peptides and Proteins, vol. 7, Weinstein, B. Editor, Marcel Dekker, New York, 1983, p. 267.
98. Perdew, J.P.; Wang, Y.; Phys. Rev. B, 1992, 45, 13244.
99. (a) Allmendiger, T.; Felder, E.; Hungerbühler, A. Tetr. Lett., 1990, 7301.
100. (b) Bartlett, P.A.; Otake, A. J. Org. Chem., 1995, 60, 3107.
101. Hodgkin, E.E.; Richards, W. G. Int. J. Q. Chem., Quantum Biology Symp., 1987, 14, 1051.
102. Breck, D.W. Zeolite Molecular Sieves: Structure, Chemistry and Use, John Wiley, Canada, 1974.
103. Uytterhoeven, J.B.; Christner, L.G.; Hall, W.K. J. Phys. Chem., 1965, 69, 2117.
104. Van Bekkum, H.; Flanigen, E.M.; Jansen, J.C. Introduction to Zeolite Science and Practice, Elsevier, Amsterdam, 1991.
105. Sherman, J.D.; Proc. Natl. Acad. Sci. USA, 1999, 96, 3471.
106. Van Genechten, K.; Mortier, W.J.; Geerlings, P. J. Chem. Phys., 1987, 86, 5063.
107. Langenaeker, W.; De Proft, F.; Geerlings, P. Recent Developments in Physical Chemistry, Vol. 2, Transworld Research Network, Triviandum, India, 1998, 1219.
108. Peirs, J.C.; De Proft, F.; Baron, G.; Van Alsenoy, C.; Geerlings, P. Chem. Comm., 1997, 531.
109. Tielens, F.; Langenaeker, W.; Ocakoglu, A. R.; Geerlings, P. J. Comp. Chem., 2000, 21, 909.
110. Tielens, F.; Geerlings, P. J. Mol. Catal., 2001, A166, 175.
111. Ruthven, D. M. Principles of Adsorption and Adsorption Processes, John Wiley, Canada, 1984.
112. Kiselev, A. V. Pure Appl. Chem., 1980, 52, 2161.
113. (a) Tielens, F.; Geerlings, P. Int. J. Quant. Chem. 2001, 84, 58.
114. (b) Tielens, F.; Geerlings, P. Chem. Phys. Lett. 2002, 354, 474.
115. Buckingham, A.D. in Intermolecular Interactions, Pullman, B. Editor, Wiley, 1988.
116. Dunning Jr., T.H. J. Chem. Phys., 1989, 90, 1007.
117. Kendall, R.A.; Dunning Jr., T.H.; Harrison, R.J. J. Chem. Phys., 1992, 96, 6796.
118. De Proft, F.; Tielens, F.; Geerlings, P. J. Mol. Struct. (Theochem), 2000, 506, 1.
119. Langenaeker, W.; De Proft, F.; Tielens, F.; Geerlings, P. Chem. Phys. Lett., 1998, 288, 628.
120. Chatterjee, A.; Iwasaki, T.; Ebina, T. J. Phys. Chem. A 1999, 103, 2489.
121. Chatterjee, A.; Iwasaki, T. J. Phys. Chem. A 1999, 103, 9857.
122. Chatterjee, A.; Iwasaki, T. J. Phys. Chem. A 2001, 105, 6187.
123. Baeten, A.; Maes, D.; Geerlings, P. J. Theoret. Biol., 1998, 195, 27.
124. Mignon, P.; Loverix, S.; Van Houtven, S.; Steyaert, J.; Geerlings, P. in preparation.
125. Carter, P.; Wells, J.A. Nature, 1988, 332, 565.
126. Russell, A.J.; Fersht, A.R J. Mol. Biol., 1987, 193, 803.
127. Bott, R.; Vetsch, M.; Kossiakoff, A.; Graycar, T.; Katz, B.; Power, S. J. Biol. Chem., 1988, 263, 7895.
128. Fersht, A. Enzyme Structure and Mechanism, New York, W.H. Freeman and Co., 1985.
129. Wells, J.A.; Estell, D.A. TIBS, 1988, 13, 291 (1988).
130. Geerlings, P.; De Proft, F.; Langenaeker, W. Editors, Density Functional Theory: a Bridge between Chemistry and Physics, Proceedings of a Two Day Symposium at the VUB, May 14-15, 1998, VUB-Press, Brussels, 1999.