Mechanism of nucleophilic substitutions at phenacyl bromides with pyridines. A computational study of intermediate and transition state

Journal of Physical Organic Chemistry

Volumn 21, Issue 11, 2008, Pages 988-996

  Fábián, Attila ^a   Ruff, Ferenc ^a   Farkas, Ödön ^a  

^a EÖTVÖS LORÁND UNIVERSITY   (Hungary)

Author keywords

Activation strain analysis; DFT calculations; Free energy of activation; Nucleophilic substitution; Phenacyl bromides; Substituent constants for pyridines; Substituent effect

Indexed keywords

ACTIVATION ANALYSIS; ACTIVATION ENERGY; ATOMIC PHYSICS; ATOMS; BROMINE COMPOUNDS; FREE ENERGY; PROBABILITY DENSITY FUNCTION; SULFUR COMPOUNDS;

ACTIVATION STRAIN ANALYSIS; DFT CALCULATIONS; FREE ENERGY OF ACTIVATION; NUCLEOPHILIC SUBSTITUTION; PHENACYL BROMIDES; SUBSTITUENT CONSTANTS FOR PYRIDINES; SUBSTITUENT EFFECT;

PYRIDINE;

EID: 55849114409     PISSN: 08943230     EISSN: 10991395     Source Type: Journal    
DOI: 10.1002/poc.1412     Document Type: Article

References (82)

1. M. J. S. Dewar, The Electronic Theory of Organic Chemistry. Oxford University Press, Oxford, 1949, p. 73.
2. E. L. Eliel, Steric Effect in Organic Chemistry, (Ed.: M. S. Newman). Wiley, New York, 1956, p. 103.
3. J. Hine, Physical Organic Chemistry (2nd edn), McGraw-Hill, New York, 1962. p. 176.
4. C. A. Bunton, Nucleophilic Substitution at a Saturated Carbon Atom, Elsevier, London, 1963, p. 35.
5. E. M. Kosower, An Introduction to Physical Organic Chemistry, Wiley, New York, 1968. pp. 77-79.
6. F. G. Bordwell, W. T. Brannen, J. Am. Chem. Soc. 1964, 86, 4645-4650.
7. S. D. Ross, M. Finkelstein, R. C. Petersen, J. Am. Chem. Soc. 1968, 90, 6411-6415.
8. J. W. Thorpe, J. Warkentin, Can. J. Chem. 1973, 51, 927-935.
9. L. M. Litvinenko, L. A. Perelman, Zh. Org. Khim. 1967, 3, 936-941.
10. L. M. Litvinenko, L. A. Perelman, Reakt. Sposob. Org. Soedin. 1971, 8, 331-342.
11. I. Lee, C. S. Shim, S. Y. Chung, H. W. Lee, J. Chem. Soc. Perkin Trans. 2 1988, 975-981.
12. I. Lee, C. S. Shim, H. W. Lee, J. Phys. Org. Chem. 1989, 2, 484-490.
13. S. J. Winston, R J. Rao, B. Sethuram, T. N. Rao, Indian J. Chem. Section A 1996, 35A, 979-982.
14. M. K. Pillay, R. Jeyaraman, M. Nallu, R Venuvanalingam, M. Ramalingam, Indian J. Chem. Section A 1997, 36A, 414-417.
15. M. Abboud, R. Notario, J. Bertran, M. Sola, Prog. Phys. Org. Chem. 1993, 19, 104-181.
16. A. Halvorsen, J. Songstad, J. Chem. Soc. Chem. Commun. 1978, 327-328.
17. R. G. Pearson, S. H. Langer, F. V. Williams, W. J. McGuire, J. Am. Chem. Soc. 1952, 74, 5130-5132.
18. J. W. Baker, Trans. Faraday Soc. 1941, 37, 632-641.
19. S. Winstein, E. Grunwald, H. W. Jones, J. Am. Chem, Soc. 1951, 73, 2700-2707.
20. W. Forster, R. M. Laird, J. Chem. Soc. Perkin Trans. 2 1982, 135-138.
21. W. Forster, R. M. Laird, J. Chem, Soc. Perkin Trans. 2 1991, 1033-1044.
22. T. L. Yousaf, E. S. Lewis, J. Am. Chem. Soc. 1987, 109, 6137-6142.
23. D. Kost, K. Aviram, Tetrahedron Lett. 1982, 4157-4160.
24. I. Lee, I. C. Kim, Bull. Korean Chem, Soc. 1988, 9, 133-135.
25. I. Lee, S. W. Hong, J. H. Park, Bull, Korean Chem, Soc. 1989, 10, 459-462.
26. D. M. Kalendra, B. R. Sickles, J. Org. Chem. 2003, 68, 1594-1596.
27. D. J. McLennan, A. Pross, J. Chem, Soc. Perkin Trans, 2 1984, 981-984.
28. D. N. Kevill, C-B. Kim, J. Org, Chem, 2004, 70, 1490-1493.
29. H. J. Koh, K. L. Han, H. W. Lee, I. Lee, J. Org. Chem. 2000, 65, 4706-4711.
30. I. Lee, H. W. Lee, Y. K. Yu, Bull. Korean Chem, Soc. 2003, 24, 993-997.
31. K. S. Lee, K. K. Adhikary, H. W. Lee, B-S. Lee, I. Lee, Org. Biomol. Chem. 2003, 1, 1989-1994.
32. F. Ruff, Ö. Farkas, J. Org. Chem. 2006, 71, 3409-3416.
33. F. Ruff, Ö. Farkas, A. Kucsman, Eur. J. Org. Chem, 2006, 5570-5580.
34. F. Ruff, Ö. Farkas, J. Phys. Org. Chem. 2008, 21, 53-61.
35. H. B. Bürgi, J. R. Dunitz, E. J. Shefter, J. Am, Chem, Soc. 1973, 95, 5065-5067.
36. H. B. Bürgi, J. M. Lehn, G. Wipff, J. Am. Chem. Soc. 1974, 96, 1956-1957.
37. H. B. Bürgi, J. R. Dunitz, J. M. Lehn, G. Wipff, Tetrahedron 1974, 31, 1563-1570.
38. E. L. Eliel, S. H. Wilen, Stereochemistry of Organic Compounds, Wiley, New York, 1994, p. 685, 737, 877.
39. F. M. Bickelhaupt, J. Comput. Chem. 1999, 20, 114-128.
40. G. T. de Jong, F. M. Bickelhaupt, ChemPhysChem. 2007, 8, 1170-1181.
41. L. Pauling, J. Am. Chem. Soc. 1947, 69, 542-553.
42. A. Shunmugasunda ram, S. Balakumar, Indian J. Chem, Section A 1985, 24A, 775-777.
43. [49] to result from changes of the structure of the TS in single-step reaction.
44. O. Exner, Advances in Linear Free Energy Relationships, (Eds: N. B., Chapman, J. Shorter,) Plenum Press, London, 1972, Ch 1.
45. R. A. Y. Jones, Physical and Mechanistic Organic Chemistry, Cambridge University Press, Cambridge, 1984, pp. 43-45.
46. N. S. Isaacs, Physical Organic Chemistry, Longman-Harlow, England, 1987, pp. 146-148.
47. F. Ruff, I. G. Csizmadia, Organic Reactions, Equilibria, Kinetics and Mechanism, Elsevier, Amsterdam, 1994, pp. 170-177.
48. J. Clayden, N. Greeves, S. Warren, P. Wothers, Organic Chemistry, Oxford University Press, Oxford, 2001, pp. 1090-1100.
49. W. P. Jencks, S. R. Brant, J. R. Gandler, G. Fendrich, C. Nakamura, J. Am. Chem. Soc. 1982, 104, 7045-7051.
50. C. G. Swain, C. B. Scott, J. Am. Chem. Soc. 1953, 75, 141-147.
51. P. R. Wells, Chem. Rev. 1963, 63, 171-219.
52. J. Koskikallio, Acta Chem. Scand. 1969, 23, 1477-1490.
53. A. Fischer, W. J. Galloway, J. Vaughan, J. Chem. Soc. 1964, 3591-3596.
54. A. Fischer, W. J. Galloway, J. Vaughan, J. Chem. Soc. 1964, 3596-3599.
55. J. A. Zoltewicz, Adv. Heterocycl. Chem. 1978, 22, 71-121.
56. E. V. Anslyn, D. A. Dougherty, Modern Physical Organic Chemistry, University Science Books, Sausalito, 2006. p. 655.
57. I. Lee, C. K. Kim, I. S. Han, H. W. Lee, W. K. Kim, Y. B. Kim, J. Chem. Phys. B 1999, 103, 7302-7307.
58. S. W. Hong, H. J. Koh, I. Lee, J. Phys. Org. Chem. 1999, 12, 425-429.
59. C. D. Johnson, I. Roberts, P. G. Taylor, J. Chem. Soc. Perkin Trans. 2 1981, 409-413.
60. R. Gallo, C. Roussel, Adv. Heterocycl. Chem. 1988, 43, 191-193.
61. K. J. Schaper, Arch. Pharm. 1978, 311, 641-650.
62. K. Clarke, K. Rothwell, J. Chem. Soc. 1960, 1885-1893.
63. C. Srinivasan, A. Shunmugasundarum, N. Arumugam, J. Chem. Soc. Perkin Trans. 2 1985, 17-19.
64. S.-D. Yoh, K.-H. Yang, I.-S, Han, Tetrahedron 1987, 43, 4089-4096.
65. S.-D. Yoh, O.-S. Lee, Tetrahedron Lett. 1988, 29, 4431-4434.
66. O.-S. Lee, S.-D. Yoh, Bull. Korean Chem. Soc. 1985, 6, 99-102.
67. H. H. Jaffe, Chem, Rev, 1953, 53, 191-261.
68. W. P. Jencks, Prog. Phys. Org. Chem, 1964, 2, 63-118.
69. W. J. Boyer, P. Zuman, J. Chem. Soc. Perkin Trans. 2 1973, 786-790.
70. M. P. Crampton, J. Chem. Soc. Perkin Trans. 2 1975, 185-189.
71. R. A. Y. Jones, Physical and Mechanistic Organic Chemistry, Cambridge University Press, Cambridge, 1984, p. 269.
72. 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. Peterson, 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. Hartchian, J. B. Cross, C. Adamo, C. 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. Daprich, 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. Komáromi, R. L. Martin, D. J. Fox, T. Keith, L. 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 B.01, Gaussian Inc., Pittsburg, PA, 2003.
73. A. P. Bento, M. Sola, F. M. Bickelhaupt, J. Comput. Chem. 2005, 26, 1497-1504.
74. M. Swart, M. Sola, F. M. Bickelhaupt, J. Comput. Chem. 2007, 28, 1551-1560.
75. J. Tomasi, M. Persico, Chem. Rev. 1994, 94, 2027-2094.
76. E. Cancès, B. Mennucci, J. Chem. Phys. 2000, 114, 4744-4745.
77. D. M. Chipman, J. Chem. Phys. 2000, 112, 5558-5568.
78. D. A. McQuarrie, J. D. Simon, Molecular Thermodynamics, University Science Books, Sausalito, CA, 1999.
79. http://www.gaussian.cam/g_whitepap/thermo/thermo.pdf
80. S. W. Benson, F. R. Cruickshank, D. M. Golden, G. R. Haugen, H. E. O'Neal, A. S. Rodgers, R. Shaw, R. Walsh, Chem. Rev. 1969, 69, 279-290.
81. S. W. Benson, Thermochemical Kinetics, Wiley, New York, 1976. pp. 19-72.
82. C. Hansch, H. Leo, R. W. Taft, Chem. Rev. 1991, 91, 165-195.