Proximity vs. strain in intramolecular ring-closing reactions

Molecular Physics

Volumn 108, Issue 13, 2010, Pages 1723-1730

  Karaman, Rafik ^a  

^a AL QUDS UNIVERSITY   (Palestine)

Author keywords

ab initio; computational chemistry; electronic structure; quantum chemistry

Indexed keywords

AB INITIO; ATTACK ANGLE; DFT AND AB INITIO; INTRAMOLECULAR CYCLIZATIONS; PRODRUGS; RING-CLOSING REACTIONS;

ACTIVATION ENERGY; CYCLIZATION; ELECTRONIC PROPERTIES; ELECTRONIC STRUCTURE; QUANTUM CHEMISTRY; QUANTUM THEORY; RADIOACTIVITY LOGGING;

COMPUTATIONAL CHEMISTRY;

EID: 77954655311     PISSN: 00268976     EISSN: 13623028     Source Type: Journal    
DOI: 10.1080/00268976.2010.489522     Document Type: Article

References (86)

1. For a review of this topic, see A. W. Czarnik, in Mechanistic Principles of Enzyme Activity, edited by J. F. Liebman and A. Greenberg (VCH, New York, 1988);
2. T. C. Bruice and S. J. Benkovic, Bioorganic Mechanisms, Vols. I and II (Benjamin, Reading, MA, 1966);
3. W. P. Jencks, Catalysis in Chemistry and Enzymology (McGraw, New York, 1969);
4. M. L. Bender, Mechanism of Homogeneous Catalysis from Protons to Proteins (Wiley-Interscience, New York, 1971);
5. D. L. Nelson and M. M. Cox, Lehninger Principles of Biochemistry (Worth, New York, 2003);
6. A. Fersht, Structure and Mechanism in Protein Science: A guide to Enzyme Catalysis and Protein Folding (W. H. Freeman, New York, 1999);
7. R. Pascal, Eur. J. Org. Chem. 1813 (2003);
8. R. Pascal, Bioorg. Chem. 31, 485 (2003);
9. G. F. Sweigers, Mechanical Catalysis (Wiley, Hoboken, NJ, 2008);
10. C. Walsh, Enzymatic Reaction Mechanism (Freeman, San Francisco, 1979);
11. M. I. Page, in Enzyme Mechanisms, edited by M. I. Page and A. Williams (Royal Society of Chemistry, London, 1987), p. 1;
12. R. B. Silverman, The Organic Chemistry of Enzyme-Catalyzed Reactions (Academic Press, San Diego, 2002);
13. R. Pascal, Eur. J. Org. Chem. 1813 (2003);
14. D. A. Kraut, K. S. Carroll and D. Herschlag, Annu. Rev. Biochem. 72, 517 (2003);
15. A. Radzicka and R. Wolfenden, J. Am. Chem. Soc. 118, 6105 (1996);
16. M. J. Snider and R. Wolfenden, J. Am. Chem. Soc. 122, 11507 (2000);
17. M. I. Page and W. P. Jencks, Proc. Natn. Acad. Sci. USA 68, 1678 (1971);
18. M. I. Page and W. P. Jencks, Gazz. Chim. Ital. 117, 455 (1987);
19. M. I. Page, Chem. Soc. Rev. 2, 295 (1973);
20. M. I. Page, Angew. Chem. Int. Ed. Engl. 16, 449 (1977).
21. F. M. Menger and M. Ladika, J. Org. Chem. 35, 3006 (1990);
22. F. M. Menger and M. Ladika, J. Am. Chem. Soc. 110, 6794 (1988);
23. F. M. Menger, Acc. Chem. Res. 18, 128 (1985);
24. F. M. Menger, J. F. Chow, H. Kaiserman and P. C. Vasquez, J. Am. Chem. Soc. 105, 4996 (1983);
25. F. M. Menger, Tetrahedron 39, 1013 (1983);
26. F. M. Menger, J. Grosssman and D. C. Liotta, J. Org. Chem. 48, 905 (1983);
27. F. M. Menger, A. L. Galloway and D. G. Musaev, Chem. Commun. 2370 (2003);
28. F. M. Menger, Pure Appl. Chem. 77, 1873 (2005) and references therein.
29. T. C. Bruice and F. L. Lightstone, Acc. Chem. Res. 32, 127 (1999);
30. F. L. Lightstone and T. C. Bruice, J. Am. Chem. Soc. 119, 9103 (1997);
31. F. L. Lightstone and T. C. Bruice, J. Am. Chem. Soc. 118, 2595 (1996);
32. F. L. Lightstone and T. C. Bruice, J. Am. Chem. Soc. 116, 10789 (1994);
33. T. C. Bruice and W. C. Bradbury, J. Am. Chem. Soc. 90, 3803 (1968);
34. T. C. Bruice and W. C. Bradbury, J. Am. Chem. Soc. 87, 4846 (1965);
35. T. C. Bruice and U. K. Pandit, J. Am. Chem. Soc. 82, 5858 (1960);
36. T. C. Bruice and U. K. Pandit, Proc. Natn. Acad. Sci. USA 46, 402 (1960).
37. A. Dafforn and D. E. Koshland, Jr., Proc. Natn. Acad. Sci. USA 68, 2463 (1971);
38. A. Dafforn and D. E. Koshland, Jr., Bioorg. Chem. 1, 129 (1971).
39. S. Milstein and L. A. Cohen, J. Am. Chem. Soc. 92, 4377 (1970);
40. S. Milstein and L. A. Cohen, Proc. Natn. Acad. Sci. USA 67, 1143 (1970);
41. S. Milstein and L. A. Cohen, J. Am. Chem. Soc. 94, 9158 (1972).
42. A. Greenberg and J. F. Liebman, Strained Organic Molecules (Academic Press, New York, 1978);
43. J. F. Liebman and A. Greenberg, Chem. Rev. 78, 311 (1976).
44. R. Karaman, Tetrahedron Lett. 49, 5998 (2008);
45. R. Karaman, Bioorg. Chem. 37, 11 (2009);
46. R. Karaman, Tetrahedron Lett. 50, 452 (2009);
47. R. Karaman, Res. Lett. Org. Chem. doi: 10.1155/2009/240253;
48. R. Karaman, Bioorg. Chem. 37, 106 (2009);
49. R. Karaman, J. Mol. Struct. 910, 27 (2009);
50. R. Karaman, Tetraderon Lett. 50, 6083 (2009);
51. R. Karaman, J. Mol. Struct. (Theochem) 939, 69 (2010);
52. R. Karaman, Tetrahedron Lett. 50 (2009) 7304;
53. R. Karaman, J. Mol. Struct. (Theochem) 940, 70 (2010).
54. R. F. Brown and N. M. Van Gulick, J. Org. Chem. 21, 1046 (1956).
55. L. Ruzicka, Chem. Ind. (London) 54, 2 (1935).
56. For reviews on early studies, see G. Illuminati and L. Mandolini, Acc. Chem. Res. 14, 95 (1981);
57. L. Mandolini, Adv. Phys. Org. Chem. 22, 1 (1986).
58. C. Galli, G. Illuminati and L. Mandolini, J. Am. Chem. Soc. 95, 8374 (1973);
59. C. Galli, G. Illuminati, L. Mandolini and P. Tamborra, J. Am. Chem. Soc. 99, 2591 (1977);
60. L. Mandolini, J. Am. Chem. Soc. 100, 550 (1978).
61. M. A. Casadei, C. Galli and L. Mandolini, J. Am. Chem. Soc. 106, 1051 (1984).
62. G. Illuminati, L. Mandolini and B. Masci, J. Am. Chem. Soc. 97, 4960 (1975);
63. G. Illuminati, L. Mandolini and B. Masci, J. Am. Chem. Soc. 99, 6308 (1977);
64. L. Mandolini, B. Masci and S. Roelens, J. Org. Chem. 42, 3733 (1977);
65. A. Dalla Cort, L. Mandolini and B. Masci, J. Org. Chem. 45, 3923 (1980);
66. A. Dalla Cort, G. Illuminati, L. Mandolini and B. Masci, J. Chem. Soc. Perkin Trans. 2 1774 (1980).
67. C. Galli, P. Gargano and L. Mandolini, Gazz. Chim. Ital. 116, 653 (1986).
68. C. Galli, G. Illuminati and L. Mandolini, J. Org. Chem. 45, 311 (1980).
69. C. Galli and L. Mandolini, Eur. J. Org. Chem. 3117 (2000).
70. http://www.gaussian.com
71. U. Burker and N. L. Allinger, Molecular Mechanics (American Chemical Society, Washington, DC, 1982).
72. C. J. Casewit, K. S. Colwell and A. K. Rappe', J. Am. Chem. Soc. 114, 10024 (1992);
73. C. J. Casewit, K. S. Colwell and A. K. Rappe', J. Am. Chem. Soc. 114, 10035 (1992);
74. C. J. Casewit, K. S. Colwell and A. K. Rappe', J. Am. Chem. Soc. 114, 10046 (1992).
75. M. J. S. Dewar, E. G. Zoebisch, E. F. Healy and J. J. P. Stewart, J. Am. Chem. Soc. 107, 3902 (1985).
76. J. N. Murrell and K. J. Laidler, Trans. Faraday Soc. 64, 371 (1968).
77. K. Fukui, Acc. Chem. Res. 14, 363 (1981);
78. K. Muller, Angew. Chem. Int. Ed. Engl. 19, 1 (1980).
79. M. T. Cancès, B. Mennucci and J. Tomasi, J. Chem. Phys. 107, 3032 (1997);
80. B. Mennucci and J. Tomasi, J. Chem. Phys. 106, 5151 (1997);
81. B. Mennucci, E. Cances and J. Tomasi, J. Phys. Chem. B 101, 10506 (1997);
82. J. Tomasi, B. Mennucci and E. Cancès, J. Mol. Struct. (Theochem) 464, 211 (1999).
83. s Exp values were calculated by different methods. For further information, see K. H. Wiberg and R. F. Waldron, J. Am. Chem. Soc. 113, 7697 (1991);
84. J. M. Brown, A. D. Conn, G. Pilcher, M. L. P. Leitao and Y. Meng-Yan, Chem. Commun. 1817 (1989);
85. H. J. Rodriguez, J.-C. Chang and T. F. Thomas, J. Am. Chem. Soc. 98, 2027 (1976);
86. H. J. Rodriguez and I. H. Williams, J. Chem Soc. Perkin Trans. 2 953 (1997).