Local softness and hardness based reactivity descriptors for predicting intra- and intermolecular reactivity sequences: Carbonyl compounds

Journal of Physical Chemistry A

Volumn 102, Issue 21, 1998, Pages 3746-3755

  Roy, R K ^a,b   Krishnamurti, S ^a   Geerlings, P ^b   Pal, S ^a  

^a NATIONAL CHEMICAL LABORATORY   (India)

^b VRIJE UNIVERSITEIT BRUSSEL   (Belgium)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0001288871     PISSN: 10895639     EISSN: None     Source Type: Journal    
DOI: 10.1021/jp973450v     Document Type: Article

References (49)

1. Pearson, R. G. J. Am. Chem. Soc. 1963, 85, 3533.
2. (a) Chemical Hardness (Structure and Bonding 80); Sen, K. D., Ed.; Springer-Verlag: Berlin, Heidelberg, 1993.
3. (b) Acc. Chem. Res. 1993, 26, contributions by Pearson, R. G.; Parr, R. G.; Zhou, Z.
4. (c) Geerlings, P.; De Proft, F.; Martin, J. M. L. in Recent Developments and Applications of Modem Density Functional Theory (Theoretical and Computational Chemistry, Vol. 4, pp 773-809); Seminario, J. M., Ed.; Elsevier: New York, 1996.
5. (d) Baeten, A.; Maes, D.; Geerlings, P. J. Theor. Biol., submitted for publication.
6. Parr, R. G.; Pearson, R. G. J. Am. Chem. Soc. 1983, 105, 7512.
7. Parr, R. G.; Chattaraj, P. K. J. Am. Chem. Soc. 1991, 113, 1854.
8. Parr, R. G.; Yang, W. J. Am. Chem. Soc. 1984, 106, 4049.
9. (a) Ghosh, S. K.; Berkowitz, M. J. Chem. Phys. 1985, 83, 2976.
10. (b) Yang, W.; Parr, R. G. Proc. Natl. Acad. Sci. U.S.A. 1985, 82, 6723. Berkowitz, M.; Parr, R. G. J. Chem. Phys. 1988, 88, 2554.
11. (b) Yang, W.; Parr, R. G. Proc. Natl. Acad. Sci. U.S.A. 1985, 82, 6723. Berkowitz, M.; Parr, R. G. J. Chem. Phys. 1988, 88, 2554.
12. Krishnamurti, S. M.; Roy, R. K.; Vetrivel, R.; Iwata, S.; Pal, S. J. Phys. Chem. 1997, 101, 7253.
13. Parr, R. G.; Yang, W. Density Functional Theory of Atoms and Molecules; Oxford University Press: New York; Clarendon Press: Oxford, 1989.
14. Gázquez, J. L.; Méndez, F. J. Phys. Chem. 1994, 98, 4591.
15. (a)De Proft, F.; Langenaeker, W.; Geerlings, P. J. Phys. Chem. 1993, 97, 1826.
16. (b) Langenaeker, W.; Coussement, N.; De Proft, F.; Geerlings, P. J. Phys. Chem. 1994, 98, 3010.
17. (c) De Proft, F.; Amira, S.; Choho, K.; Geerlings, P. J. Phys. Chem. 1994, 98, 5227.
18. (d) De Proft, F.; Langenaeker, W.; Geerlings, P. Int. J. Quantum Chem. 1995, 55, 459.
19. (e) De Proft, F.; Langenaeker, W.; Geerlings, P. Tetrahedron 1995, 51, 4021.
20. (f) Baeten, A.; De Proft, F.; Geerlings, P. Chem. Phys. Lett. 1995, 235, 17.
21. (a) Ghosh, S. K. Chem. Phys. Lett. 1990, 172, 77.
22. (b) Harbola, M. K.; Chattaraj, P. K.; Parr, R. G. Isr. J. Chem. 1991, 31, 395.
23. Langenaeker, W.; De Proft, R; Geerlings, P. J. Phys. Chem. 1995, 99, 6424.
24. Parr, R. G.; Donnelly, R. A.; Levy, M.; Palke, W. E. J. Chem. Phys, 1978, 68, 3801.
25. Iczkowski, R. P.; Margrave, J. L. J. Am. Chem. Soc. 1961, 83, 3547.
26. Nalewajski, R. F.; Parr, R. G. J. Chem. Phys. 1982, 77, 399.
27. Yang, W.; Mortier, W. J. J. Am. Chem. Soc. 1986, 108, 5708.
28. Bonaccorsi, R.; Scrocco, E.; Tomasi, J. J. Chem. Phys. 1970, 52, 5270.
29. Unichem, Cray Research Inc., Eagon, MN, 1994.
30. Huzinaga, S. J. Chem. Phys, 1965, 42, 1293.; Dunning, T. H. J. Chem. Phys. 1970, 53, 2823.
31. Huzinaga, S. J. Chem. Phys, 1965, 42, 1293.; Dunning, T. H. J. Chem. Phys. 1970, 53, 2823.
32. Frish, M. J.; Trucks, G. W.; Schlegel, H. B.; Gill, P. M. W.; Johnson, B. G.; Robb, M. A.; Cheeseman, J. R.; Keith, T.; Petersson, G. A.; Montgomery, J. A.; Raghavachari, K.; Al-Laham, M. A.; Zakrzewski, V. G.; Ortiz, J. V..; Foresman, J. B.; Peng, C. Y.; Ayala, P. Y.; Chen, W.; Wong, M. W.; Andres, J. L.; Replogle, E. S.; Gomperts, R.; Martin, R. L.; Fox, D. J.; Binkley, J. S.; Defrees, D. J.; Baker, J.; Stewart, J. J. P.; Head-Gordon, M.; Gonzalez, C.; Pople, J. A. Gaussian 94, Revision B. 3; Gaussian Inc.: Pittsburgh, PA, 1995.
33. Hehre, W. J.; Radom, L.; Schleyer, P. v. R.; Pople, J. A. Ab Initio Molecular Orbital Theory; John Wiley: New York, 1986.
34. (a) Cherest, M.; Felkin, H. Tetrahedron Lett. 1968, 2205.
35. (b) Cherest, M.; Felkin, H.; Prudent, N. Tetrahedron Lett. 1968, 2199.
36. (c) Cherest, M.; Felkin, H.; Tacheau, P.; Jacques, J.; Varech, D. J. Chem. Soc., Chem. Commun. 1977, 372.
37. (d) Anh, N. T. Regio- and Stereo-Selectivities in Some Nucleophilic Reactions: Top. Curr. Chem. 1980, 88, 145.
38. (a) Bürgi, H. B.; Dunitz, J. D.; Lehn, J. M.; Wipff, G. Tetrahedron 1974, 30, 1563.
39. (b) Bürgi, H. B.; Dunitz, J. D.; Shefter, E. J. J. Am. Chem. Soc. 1973, 95, 5065.
40. (c) Bürgi, H. B.; Lehn, J. M.; Wipff, G. J. Am. Chem. Soc. 1974, 96, 1956.
41. (a) Patai, S.; Rappoport, Z. In The Chemistry of Alkenes; Interscience Publishers: London, 1964, p 469. Wong, S. S.; Paddon-Row: M. N.; Li, Y.; Houk, K. N. J. Am. Chem. Soc. 1990, 112, 8679. Langenaeker, W.; Demel, K.; Geerlings, P. J. Mol. Struct. (THEOCHEM) 1992, 259, 317. Dorigo, A. E.; Morokuma, K. J. Am Chem. Soc. 1989, 111, 6524.
42. (a) Patai, S.; Rappoport, Z. In The Chemistry of Alkenes; Interscience Publishers: London, 1964, p 469. Wong, S. S.; Paddon-Row: M. N.; Li, Y.; Houk, K. N. J. Am. Chem. Soc. 1990, 112, 8679. Langenaeker, W.; Demel, K.; Geerlings, P. J. Mol. Struct. (THEOCHEM) 1992, 259, 317. Dorigo, A. E.; Morokuma, K. J. Am Chem. Soc. 1989, 111, 6524.
43. (a) Patai, S.; Rappoport, Z. In The Chemistry of Alkenes; Interscience Publishers: London, 1964, p 469. Wong, S. S.; Paddon-Row: M. N.; Li, Y.; Houk, K. N. J. Am. Chem. Soc. 1990, 112, 8679. Langenaeker, W.; Demel, K.; Geerlings, P. J. Mol. Struct. (THEOCHEM) 1992, 259, 317. Dorigo, A. E.; Morokuma, K. J. Am Chem. Soc. 1989, 111, 6524.
44. (a) Patai, S.; Rappoport, Z. In The Chemistry of Alkenes; Interscience Publishers: London, 1964, p 469. Wong, S. S.; Paddon-Row: M. N.; Li, Y.; Houk, K. N. J. Am. Chem. Soc. 1990, 112, 8679. Langenaeker, W.; Demel, K.; Geerlings, P. J. Mol. Struct. (THEOCHEM) 1992, 259, 317. Dorigo, A. E.; Morokuma, K. J. Am Chem. Soc. 1989, 111, 6524.
45. (b) Negishi, E. Organometallics in Organic Synthesis, Vol. 1; Wiley: New York, 1980, pp 127-133. March, J. Advanced Organic Chemistry: Reactions, Mechanisms and Structure, 4th ed.; John Wiley & Sons: New York, 1992; p 881.
46. (b) Negishi, E. Organometallics in Organic Synthesis, Vol. 1; Wiley: New York, 1980, pp 127-133. March, J. Advanced Organic Chemistry: Reactions, Mechanisms and Structure, 4th ed.; John Wiley & Sons: New York, 1992; p 881.
47. Schaefer, H. F. In Rappoport, Ed. The Chemistry of the Cyano Group; Wiley: New York, 1970; pp 239-305.
48. Damoun, S.; Langenaeker, W.; Van de Woude, G.; Geerlings, P. J. Phys. Chem. 1995, 99, 12151.
49. Sjoberg, P.; Politzer, P. J. Phys. Chem. 1990, 94, 3959.