A DFT study of transition structures and reactivity in solvolyses of tert-butyl chloride, cumyl chlorides, and benzyl chlorides

Journal of Physical Organic Chemistry

Volumn 21, Issue 1, 2008, Pages 53-61

  Ruff, Ferenc ^a   Farkas, Ödön ^a  

^a EÖTVÖS LORÁND UNIVERSITY   (Hungary)

Author keywords

Activation parameters; Benzyl chlorides; Cumyl chlorides; DFT calculations; Nucleophilic substitutions; Substituent effect; Tert butyl chloride

Indexed keywords

ACTIVATION ENERGY; DENSITY FUNCTIONAL THEORY; ETHANOL; REACTION KINETICS; SUBSTITUTION REACTIONS;

BENZYL CHLORIDES; CUMYL CHLORIDES; NUCLEOPHILIC SUBSTITUTIONS; TERT-BUTYL CHLORIDE;

CHLORINE COMPOUNDS;

EID: 39349103802     PISSN: 08943230     EISSN: 10991395     Source Type: Journal    
DOI: 10.1002/poc.1284     Document Type: Article

References (85)

1. a) C. K. Ingold, Structure and Mechanism in Organic Chemistry, 2nd ed., Bell, London, 1969;
2. b) S. R. Hartshorn, Aliphatic Nucleophilic Substiution, Cambridge University Press, Cambridge, 1973;
3. c) A. R. Katritzky, B. E. Brycki, Chem. Soc. Rev. 1990, 79, 83-105;
4. N2 Mechanism, Wiley, New York, 1992;
5. e) J.-L. M. Abboud, R. Notario, J. Bertran, M. Sola, Prog. Phys. Org. Chem. 1993, 19, 1-182, and references therein;
6. f) M. B. Smith, J. March, March's Advanced Organic Chemistry, Reactions, Mechanism, and Structure, 5th ed., Wiley, New York, 2001. pp. 381-462, and references therein.
7. a) H. Kim, J. T. A. Hynes, J. Am. Chem. Soc. 1992, 114, 10508-10528;
8. b) J. R. Mathis, H. Kim, J. T. A. Hynes, J. Am. Chem. Soc. 1993, 115, 8248-8262;
9. c) J. P. Richard, T. L. Amyes, M. M. Toteva, Acc. Chem. Res. 2001, 34, 981-988;
10. d) S. Minegishi, R. Loos, S. Kobayashi, H. Mayr, J. Am. Chem. Soc. 2005, 114, 2641-2649;
11. e) K. S. Peters, Ace. Chem. Res. 2007, 40, 1-7.
12. a) T. W. Bentley, P. R. Schleyer, J. Am. Chem. Soc. 1976, 98, 7658-7666;
13. b) F. L. Schadt, T. W. Bentley, P. R. Schleyer, J. Am. Chem. Soc. 1976, 98, 7667-7674;
14. c) T. W. Bentley, C. T. Bowen, D. H. Morten, P. R. Schleyer, J. Am. Chem. Soc. 1981, 103, 5466-5475;
15. d) T. W. Bentley, G. E. Carter, J. Am. Chem. Soc. 1982, 104, 5741-5747;
16. e) T. W. Bentley, C. T. Bowen, W. Parker, C. I. F. Watt, J. Am. Chem. Soc. 1979, 101, 2486-2488;
17. f) T. W. Bentley, C. T. Bowen, W. Parker, C. I. F. Watt, J. Chem. Soc., Perkin Trans. 2 1980, 1244-1252.
18. J. J. Gajewski, J. Am. Chem. Soc. 2001, 123, 10877-10883.
19. a) F. Ruff, Ö. Farkas, J. Org. Chem. 2006, 71, 3409-3416;
20. b) F. Ruff, Ö. Farkas, Á. Kucsman, Eur. J. Org. Chem. 2006, 5570-5580.
21. a) F. Ruff, J. Mol. Struct. (Theochem.) 2002, 617, 31-45;
22. b) F. Ruff, Internet Electron. J. Mol. Des. 2004, 3, 474-498. http://www.biochempress.com
23. a) L. G. Hepler, W. F. O'Hara, J. Phys. Chem. 1961, 65, 811-814;
24. b) L. G. Hepler, J. Am. Chem. Soc. 1963, 85, 3089-3092;
25. c) J. W. Larson, L. G. Hepler, J. Org. Chem. 1968, 33, 3961-3963;
26. d) L. G. Hepler, Can. J. Chem. 1971, 49, 2803-2807;
27. e) T. Matsui, L G. Hepler, Can. J. Chem. 1977, 54, 1296-1299.
28. a) W. P. Keirstead, K. R. Wilson, J. T. Hynes, J. Chem. Phys. 1991, 95, 5256-5257;
29. b) R. M. C. Goncalves, A. M. N. Simoes, L. M. P. C. Albuquerque, E. A. Macedo, J. Phys. Org. Chem. 1993, 6, 133-138;
30. c) D. S. Hartsough, K. M. Merz, J. Phys. Chem. 1995, 99, 384-390;
31. d) E. D. German, A. M. Kuznetsov, V. A. Tikhomirov, J. Electroanal. Chem. 1997, 420, 235-241;
32. e) D. D. Sung, J.-Y. Kim, I. Lee, S. S. Chung, K. H. Park, Chem. Phys. Lett. 2004, 392, 378-382.
33. S. Yamabe, E. Yamabe, T. Minato, J. Chem. Soc., Perkin Trans. 2 1983, 1881-1884.
34. M. M. Toteva, J. P. Richard, J. Am. Chem. Soc. 1996, 118, 11434-11445.
35. a) A. H. Fainberg, S. Winstein, J. Am. Chem. Soc. 1956, 78, 2770-2777;
36. b) S. Winstein, A. H. Fainberg, J. Am. Chem. Soc. 1957, 79, 5937-5950.
37. W. L. Jorgensen, J. K. Bucker, S. E. Huston, P. J. Rossky, J. Am. Chem. Soc. 1987, 109, 1891-1899.
38. A. G. Martinez, E. T. Vilar, J. O. Barcina, S. D. Cerero, J. Org. Chem. 2005, 70, 10238-10246.
39. a) H. Yamataka, M. Aida, Chem. Phys. Lett. 1998, 289, 105-109;
40. b) M. Aida, H. Yamataka, M. Dupuis, Chem. Phys. Lett. 1998, 292, 474-480;
41. c) M. Aida, H. Yamataka, M. Dupuis, Theor. Chem. Acc. 1999, 102, 262-271;
42. d) M. Aida, H. Yamataka, J. Mol. Struct. Theochem. 1999, 467, 417-427.
43. M. H. Abraham, D. J. McLennan, J. Chem. Soc., Perkin Trans. 2 1977, 873-879.
44. a) H. C. Brown, J. D. Brady, M. Grayson, W. H. Bonner, J. Am. Chem. Soc. 1957, 79, 1897-1903;
45. b) H. C. Brown, Y. Okamoto, G. Ham, J. Am. Chem. Soc. 1957, 79, 1906-1909;
46. c) Y. Okamoto, T. Inukai, H. C. Brown, J. Am. Chem. Soc. 1958, 80, 4979-4987.
47. a) H. J. Koh, H. W. Lee, I. Lee, J. Chem. Soc., Perkin Trans. 2 1994, 125-129;
48. b) I. Lee, H. J. Koh, S. N. Hong, B. S. Lee, Gozz. Chim. Ital. 1995, 125, 347-351;
49. c) S. Balachandran, R. S. Devi, D. S. Kumar, Asian J. Chem. 2005, 17, 1216-1220.
50. a) K.-T. Liu, L.-W. Chang, P.-S. Chen, J. Org. Chem. 1992, 57, 4791-4793;
51. b) K.-T. Liu, P.-S. Chen, P.-F. Chiu, M.-L. Tsao, Tetrahedron Lett. 1992, 33, 6499-6502.
52. a) V. A. Amelichev, G. V. Saidov, Zh. Obsh. Khim. 1981, 57, 187-192;
53. b) V. A. Amelichev, G. V. Saidov, Zh. Obsh. Khim. 1981, 51, 1874-1879;
54. c) V. A. Amelichev, M. V. Nosovskii, G. V. Saidov, Zh. Obsh. Khim. 1981, 51, 1879-1885.
55. D. N. Kevill, M. J. Dsouza, J. Chem. Res. -S. 1993, 332-333.
56. a) J. P. Richard, T. L. Amyes, T. Vontor, J. Am. Chem. Soc. 1991, 113, 5871-5873;
57. b) J. P. Richard, V. Jagannadham, T. L. Amyes, M. Mishima, Y. Tsuno, J. Am. Chem. Soc. 1994, 116, 6706-6712.
58. G. A. DiLabio, K. U. Ingold, J. Org. Chem. 2004, 69, 1620-1624.
59. a) G. Kohnstam, Adv. Phys. Org. Chem. 1967, 5, 121-169, and references therein;
60. b) B. J. Gregory, G. Kohnstam, A. Queen, D. J. Reed, Chem. Commun. 1971, 797-799.
61. M. P. Friedberger, E. R. Thornton, J. Am. Chem. Soc 1976, 98, 28612865.
62. D. J. McLennan, Acc. Chem. Res. 1976, 9, 281-287.
63. J. M. Harris, Prog. Phys. Org. Chem. 1974, 11, 89-173.
64. A. Queen, Can. J. Chem. 1979, 57, 2646-2657.
65. R. A. Sneen, Acc. Chem. Res. 1973, 6, 46-53.
66. H. Aronovitch, A. Porss, J. Chem. Soc, Perkin Trans. 2 1978, 540-545.
67. J. B. Hyne, R. Wills, R. E. Wonka, J. Am. Chem. Soc. 1962, 84, 2914-2919.
68. a) E. Tommila, E. Paakkala, U. K. Virtannen, A. Erva, S. Vavila, Ann. Acad. Sci. Fennicae 1959, A No. 91, 3-36;
69. b) E. Tommila, Acta Chem. Scand. 1966, 20, 923-936.
70. L Pauling, J. Am. Chem. Soc. 1947, 69, 542-553.
71. R. A. Y. Jones, Physical and Mechanistic Organic Chemistry, 2nd ed., Cambridge University Press, Cambridge, 1984, pp. 155-158, and references contained therein.
72. T. Thorstenson, R. Eliason, A. Songstad, Acta Chem. Scand. 1977, A31, 276-280.
73. F. P. Ballistreri, E. Maccarone, A. Mamo, J. Org. Chem. 1976, 41, 3364-3366.
74. a) O. Exner, in Advances in Linear Free Energy Relationships (Eds: N. B. Chapman, J. Shorter), Plenum Press, New York, 1972, Chap. 1;
75. b) F. Ruff, I. G. Csizmadia, Organic Reaction, Equilibria, Kinetics and Mechanism, Elsevier, Amsterdam, 1994.
76. 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, Ö. 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 C.02, Gaussian, Inc., Pittsburg, PA. 2003.
77. J. Tomasi, M. Persico, Chem. Rev. 1994, 94, 2027-2094.
78. E. Cancès, B. Mennucci, J. Chem. Phys. 2001, 114, 4744-4745.
79. D. M. Chipman, J. Chem. Phys. 2000, 112, 5558-5565.
80. D. A. McQuarrie, J. D. Simon, Molecular Thermodynamics, University Science Books, Sausalito, CA, 1999.
81. http://www.gaussian.com/g_whitepap/thermo/thermo.pdf
82. a) 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;
83. b) S. W. Benson, Thermochemical Kinetics, Wiley, New York, pp. 19-72.
84. CRC Handbook of Chemistry and Physics (Ed.: D. R. Lide), CRC Press, Boca Roton, 1995, Chap. 5-4.
85. C. Hansch, H. Leo, R. W. Taft, Chem. Rev. 1991, 91, 165-195.