A new interpretation of chlorine leaving group kinetic isotope effects; a theoretical approach

Journal of Organic Chemistry

Volumn 69, Issue 15, 2004, Pages 4900-4905

  Dybała Defratyka, Agnieszka ^a   Rostkowski, Michal ^a   Matsson, Olle ^b   Westaway, Kenneth C ^c   Paneth, Piotr ^a  

^a LODZ UNIVERSITY OF TECHNOLOGY   (Poland)

^b UPPSALA UNIVERSITY   (Sweden)

^c LAURENTIAN UNIVERSITY   (Canada)

Author keywords

[No Author keywords available]

Indexed keywords

ISOTOPES; MATHEMATICAL MODELS; REACTION KINETICS; SOLVENTS;

KINETIC ISOTOPE EFFECTS (KSE); NUCLEOPHILES; SOLVENT MODELS; TRANSITION STATES;

CHLORINE;

ANION; CHLORINE; ISOTOPE; METHYL CHLORIDE; RADICAL; SOLVENT;

ARTICLE; CALCULATION; CHEMICAL BOND; CHEMICAL REACTION KINETICS; GAS; KINETIC ISOTOPE EFFECT; LINEAR SYSTEM; PHASE TRANSITION; REACTION ANALYSIS; SOLVATION; THEORY;

EID: 3543029213     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo049327z     Document Type: Article

References (43)

1. (a) Melander, L.; Saunders, W. H., Jr. Reaction Rates of Isotopic Molecules; Wiley: New York, 1980.
2. (b) Isotope Effects in Enzyme Reactions; Cook, P. F., Ed.; CRC Press: Boca Raton, 1991.
3. Fang, Y.-r.; Gao, Y.; Ryberg, P.; Eriksson, J.; Kolodziejska-Huben, M.; Dybala-Defratyka, A.; Danielsson, R.; Paneth, P.; Matsson, O.; Westaway, K. C. Chem. Eur. J. 2003, 9, 2696.
4. (a) Lynch, G. C.; Truhlar, D. G.; Brown, F. B.; Zhao, J.-g. J. Phys. Chem. 1995, 99, 207.
5. (b) Topaler, M. S.; Truhlar, D. G.; Chang, X. Y.; Piecuch, P.; Polanyi, J. C. J. Chem. Phys. 1998, 108, 5378.
6. (c) Linder, D. P.; Duan, X.; Page, M. J. Chem. Phys. 1998, 104, 6298.
7. Sims, L. B.; Lewis, E. D. In Isotopes in Organic Chemistry; Buncel, E., Lee, C. C., Eds.; Elsevier: Amsterdam, 1985; Vol. 6, Chapter 4.
8. (a) Westaway, K. C.; Koerner, T.; Fang, Y.-r.; Rudziński, J.; Paneth, P. Anal. Chem. 1998, 70, 3548.
9. (b) Nešković, O. M.; Vlejković, M. V.; Veličković, S. R.; Derić, A. J.; Miljević, N. R. Nukleonika 2002, 47, S85.
10. (a) Paneth, P. Acc. Chem. Res. 2003, 36, 120.
11. (b) Sturchio, N. C.; Hatzinger, P. B.; Arkins, M. D.; Suh, C.; Heraty, L. J. Environ. Sci. Technol. 2003, 37, 3859.
12. (a) Becke, A. D. J. Chem. Phys. 1996, 104, 1040.
13. (b) Becke, A. D. J. Chem. Phys. 1993, 98, 5648.
14. (c) Lee, C.; Yang, W.; Parr, R. G. Phys. Rev. B 1988, 37, 785.
15. (a) Woon, D. E.; Dunning, T. H., Jr. J. Chem. Phys. 1993, 98, 1358.
16. (b) Clark, T.; Chandrasekhar, J.; Spitznagel, G. W.; v. R. Schleyer, P. J. Comput. Chem. 1983, 4, 294.
17. Frisch, M. J.; Trucks, G. W.; Schlegel, H. B.; Scuseria, G. E.; Robb, M. A.; Cheeseman, J. R.; Montgomery, J. A., Jr.; Vreven, T.; Kudin, K. N.; Burant, J. C.; Millam, J. M.; Iyengar, S. S.; Tomasi, J.; Barone, V.; Mennucci, B.; Cossi, M.; Scalmani, G.; Rega, N.; Petersson, G. A.; Nakatsuji, H.; Hada, M.; Ehara, M.; Toyota, K.; Fukuda, R.; Hasegawa, J.; Ishida, M.; Nakajima, T.; Honda, Y.; Kitao, O.; Nakai, H.; Klene, M.; Li, X.; Knox, J. E.; Hratchian, H. P.; Cross, J. B.; Adamo, C.; Jaramillo, J.; Gomperts, R.; Stratmann, R. E.; Yazyev, O.; Austin, A. J.; Cammi, R.; Pomelli, C.; Ochterski, J. W.; Ayala, P. Y.; Morokuma, K.; Voth, G. A.; Salvador, P.; Dannenberg, J. J.; Zakrzewski, V. G.; Dapprich, S.; Daniels, A. D.; Strain, M. C.; Farkas, O.; Malick, D. K.; Rabuck, A. D.; Raghavachari, K.; Foresman, J. B.; Ortiz, J. V.; Cui, Q.; Baboul, A. G.; Clifford, S.; Cioslowski, J.; Stefanov, B. B.; Liu, G.; Liashenko, A.; Piskorz, P.; Komaromi, L.; Martin, R. L.; Fox, D. J.; Keith, T.; Al-Laham, M. A.; Peng, C. Y.; Nanayakkara, A.; Challacombe, M.; Gill, P. M. W.; Johnson, B.; Chen, W.; Wong, M. W.; Gonzalez, C.; Pople, J. A. Gaussian 03, Revision B.01; Gaussian, Inc.: Pittsburgh, PA, 2003.
18. Wigner, E. Z. Phys. Chem. B 1932, 19, 203.
19. Pople, J. A.; Nesbet, R. K. J. Chem. Phys. 1954, 22, 571.
20. (a) Mennucci, B.; Tomasi, J. J. Chem. Phys. 1977, 706, 5151.
21. (b) Barone, V.; Cossi, M. J. Phys. Chem. A 1998, 102, 1995.
22. (c) Eckert, F.; Klamt, A. AIChE J. 2002, 48, 369.
23. Anisimov, V.; Paneth, P. J. Math. Chem. 1999, 26, 75.
24. Bochicchio, R. C.; Lain, L.; Torre, A. Chem. Phys. Lett. 2003, 374, 567.
25. Pauling, L. J. Am. Chem. Soc. 1947, 69, 542.
26. (a) Maccoll, A. J. Chem. Soc. A 1974, 71, 86.
27. (b) Buddenbaum, W. E.; Shiner, V. J., Jr. In Isotope effects on enzyme-catalyzed reactions; Cleland, W. W., O'Leary, M. H., Northrop, D. B., Eds.; University Park Press: Baltimore, 1977; p 18.
28. (c) Williams, R. C.; Taylor, J. W. J. Am. Chem. Soc. 1973, 95, 1710.
29. (d) Sims, L. B.; Fry, A.; Netherton, L. T.; Wilson, J. C.; Reppond, K. D.; Crook, S. W. J. Am. Chem. Soc. 1972, 94, 1364.
30. (e) Paneth, P. In Isotopes in Organic Chemistry; Buncel, E., Saunders, W. H., Jr., Eds.; Elsevier: New York, 1992; Vol. 8, Chapter 2.
31. Westaway, K. C. Can. J. Chem. 1978, 56, 2691
32. Westaway, K. C.; Fang, Y.-r; Persson, J.; Matsson, O. J. Am. Chem. Soc. 1998, 120, 3340.
33. Wiberg, K. B. Tetrahedron 1968, 24, 1083.
34. Mulliken, R. S. J. Chem. Phys. 1955, 23, 1833.
35. Green, D. F.; Tidor, B. J. Phys. Chem. B 2003, 107, 10261.
36. Houk, K. N.; Gustafson, S. M.; Black, K. A. J. Am. Chem. Soc. 1977, 114, 8565.
37. (a) Meyer, M. P.; DelMonte, A. J.; Singleton, D. A. J. Am. Chem. Soc. 1999,121, 10865.
38. (b) Williams, R. C.; Taylor, J. W. J. Am. Chem. Soc. 2000, 122, 1609.
39. (c) Zuev, P. S.; Sheridan, R. S.; Albu, T. V.; Truhlar, D. G.; Hrovat, D. A.; Borden, W. T. Science 2003, 299, 867.
40. (a) LeNoble, W. J.; Miller, A. R. J. Org. Chem. 1979, 44, 889.
41. (b) Swain, C. G.; Hershey, N. D. J. Am. Chem. Soc. 1972, 94, 1901.
42. (c) Hill, J. W.; Fry, A. J. Am. Chem. Soc. 1962, 84, 2763.
43. (d) Graczyk, D. C.; Taylor, J. W.; Turnquist, C. R. J. Am. Chem. Soc. 1978, 100, 7333.