An accurate theoretical study of energy barriers of alkaline hydrolysis of carboxylic esters

Research on Chemical Intermediates

Volumn 38, Issue 9, 2012, Pages 2175-2190

  Wang, Huajing ^a  

^a Tianjin Economic Technological Development Area Polytechinc   (China)

Author keywords

Alkaline ester hydrolysis; Density functional theory; Mechanisms

Indexed keywords

ALKALINE HYDROLYSIS; AQUATIC SOLUTIONS; CARBOXYLIC ESTERS; COMBINATION METHOD; ESTER HYDROLYSIS; ETHYL BENZOATE; ORGANIC SYNTHESIS; POLAR EFFECT; REACTION MECHANISM; REMOTE SUBSTITUENT EFFECTS; SOLVENT EFFECTS; STERIC EFFECT; THEORETICAL STUDY;

ACTIVATION ENERGY; ALKALINITY; DENSITY FUNCTIONAL THEORY; ENERGY BARRIERS; ESTERIFICATION; ESTERS; MECHANISMS; OXYGEN; SYNTHESIS (CHEMICAL);

HYDROLYSIS;

EID: 84871103046     PISSN: 09226168     EISSN: 15685675     Source Type: Journal    
DOI: 10.1007/s11164-012-0535-8     Document Type: Article

References (68)

1. J.M. Riveros, S.M. Joseé, K. Takashima, Adv. Phys. Org. Chem. 21, 197 (1985)
2. C.H. Depuy, S. Gronert, A. Mullin, V.M. Bierbaum, J. Am. Chem. Soc. 112, 8650 (1990)
3. S. Gronert, Chem. Rev. 101, 329 (2001)
4. T.H. Loery, K.S. Richardson, Mechanism and Theory in Organic Chemistry, 3rd edn. (Harper and Row, New York, 1987)
5. M.L. Bender, H.d'A. Heck, J. Am. Chem. Soc. 89, 1211 (1967)
6. S.A. Shain, J.F. Kirsch, J. Am. Chem. Soc. 90, 5848 (1968)
7. P.N. Rylander, D.S. Tarbell, J. Am. Chem. Soc. 70, 3021 (1950)
8. E.K. Fukuda, R.T. Mclver Jr, J. Am. Chem. Soc. 101, 2498 (1979)
9. K. Takashima, S.M. Jose, A.T. do Amaral, J.M. Riveros. J. Chem. Soc. Chem. Commun. 1255 (1983)
10. I.H. Williams, D. Spangler, D.A. Femec, G.M. Maggiora, R.L. Schowen, J. Am. Chem. Soc. 102, 6621 (1980)
11. I.H. Williams, G.M. Maggiora, R.L. Schowen, J. Am. Chem. Soc. 102, 7831 (1980)
12. I.H. Williams, D. Spangler, D.A. Femec, G.M. Maggiora, R.L. Schowen, J. Am. Chem. Soc. 105, 31 (1983)
13. C.G. Zhan, D.W. Landry, R.L. Ornstein, J. Am. Chem. Soc. 122, 1522 (2000)
14. C.G. Zhan, D.W. Landry, R.L. Ornstein, J. Am. Chem. Soc. 122, 2621 (2000)
15. M.L. Bender, Chem. Rev. 60, 53 (1960)
16. S.L. Johnson, Adv. Phys. Org. Chem. 5, 237 (1967)
17. W.P. Jencks, Chem. Rev. 72, 705 (1972)
18. C.H. Bamford, C.F.H. Tipper (eds.), Ester Formation and Hydrolysis, vol. 10 (Elsevier, Amsterdam, 1972)
19. C.K. Ingold, Structure and Mechanism in Organic Chemistry, 2nd edn. (Cornell University Press, Ithaca, New York, 1969), p. 1131
20. A.J. Kirby, in Comprehensive Chemical Kinetics, vol. 10, ed. by C.H. Bamford, C.F.H. Tipper (Elsevier, Amsterdam, 1972)
21. S.L. Jonhson, Adv. Phys. Org. Chem. 45, 911 (1967)
22. F.A. Carey, R.J. Sundberg, Advanced Organic Chemistry, Part A: Structure and Mechanisms, 3rd edn. (Plenum, New York, 1990), p. 465
23. T.H. Lowry, K.S. Richardson, Mechanism and Theory in Organic Chemistry, 2nd edn. (Harper and Row, New York, 1981), p. 650
24. M.L. Bender, R.S. Dewey, J. Am. Chem. Soc. 78, 317 (1956)
25. M.L. Bender, R.D. Ginger, J.P. Unik, J. Am. Chem. Soc. 80, 1044 (1958)
26. S.A. Shain, J.F. Kirsch, J. Am. Chem. Soc. 90, 5848 (1968)
27. M.L. Bender, Chem. Rev. 60, 53 (1960)
28. S.L. Johnson, Adv. Phys. Org. Chem. 5, 237 (1967)
29. T.C. Bruice, B. Holmquist, J. Am. Chem. Soc. 90, 7136 (1968)
30. C.G. Zhan, D.W. Landry, R.L. Ornstein, J. Phys. Chem. A. 104, 7672 (2000)
31. F. Haeffner, C.H. Hu, T. Brinck, T. Norin, THEOCHEM 459, 85 (1999)
32. D.J. Tantillo, K.N. Houk, J. Org. Chem. 64, 3066 (1999)
33. D.Q. Xie, D.G. Xu, L.D. Zhang, H. Guo, J. Phys. Chem. B 109, 5259 (2005)
34. Z.X. Yu, Y.D. Wu, J. Org. Chem. 68, 412 (2003)
35. Y. Zhao, D.G. Truhlar, J. Phys. Chem. A 108, 6908 (2004)
36. B.J. Lynch, Y. Zhao, D.G. Truhlar, J. Phys. Chem. A 107, 1384 (2003)
37. Y. Zhao, B.J. Lynch, D.G. Truhlar, Phys. Chem. Chem. Phys. 7, 43 (2005)
38. Y. Fu, H.J. Wang, S.S. Chong, R. Liu, Q.X. Guo, L. Liu, J. Org. Chem. 74, 810 (2009)
39. C.J. Cramer, D.G. Truhlar, Rev. Comput. Chem. 6, 1 (1995)
40. C.J. Cramer, D.G. Truhlar, Chem. Rev. 99, 2161 (1999)
41. T. Hou, X. Xu, Prog. Chem. 16, 153 (2004)
42. J. Tomasi, B. Mennucci, R. Cammi, Chem. Rev. 105, 2999 (2005)
43. C. Gonzalez, H.B. Schlegel, J. Chem. Phys. 90, 2154 (1989)
44. C. Gonzalez, H.B. Schlegel, J. Phys. Chem. 94, 5523 (1990)
45. 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. Petersson, 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. Hratchian, J.B. Cross, V. Bakken, C. Adamo, J. 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. Dapprich, 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. Komaromi, R.L. Martin, D.J. Fox, T. Keith, M.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, Wallingford, 2004)
46. C.G. Swain, D.A. Kuhn, R.L. Schowen, J. Am. Chem. Soc. 87, 1553 (1965)
47. M. Charton, Prog. Phys. Org. Chem. 13, 119 (1981)
48. V. Barone, M. Cossi, J. Tomasi, J. Chem. Phys. 107, 3210 (1997)
49. J. Li, T. Zhu, C.J. Cramer, D.G. Truhlar, J. Phys. Chem. A 104, 2178 (2000)
50. K. Coutinho, S. Canuto, J. Chem. Phys. 113, 9132 (2000)
51. B. Mennucci, J.M. Martinez, J. Tomasi, J. Phys. Chem. A 105, 7287 (2001)
52. A. Klamt, G.J. Schüürmann, Chem. Soc. Perkin Trans. 2, 799 (1993)
53. J. Andzelm, C. Kölmel, A. Klamt, J. Chem. Phys. 103, 9312 (1995)
54. V. Barone, M. Cossi, J. Phys. Chem. A 102, 1995-2001 (1998)
55. M. Cossi, N. Rega, G. Scalmani, V. Barone, J. Comput. Chem. 24, 669 (2003)
56. A. Klamt, J. Phys. Chem. 99, 2224 (1995)
57. A. Klamt, V. Jonas, T. Burger, J.C.W. Lohrenz, J. Phys. Chem. A 102, 5074 (1998)
58. G. Davies, D.P. Evans. J. Chem. Soc. 339 (1940)
59. R.W.A. Jones, J.D.R. Thomas. J. Chem. Soc. B. 661 (1966)
60. E. Tommila, C.N. Hinshelwood. J. Chem. Soc. 1801 (1938)
61. A.A. Humffary, J.J. Ryan. J. Chem. Soc. B. 842 (1966)
62. Robson Wright M. J. Chem. Soc. B. 1265 (1967)
63. R.W. Hay, L.J. Porter. J. Chem. Soc. B. 1261 (1967)
64. R.W. Hay, L.J. Porter, P.J. Morris. Aust. J. Chem. 19, 1197 (1966)
65. C.H. Depuy, L.R. Mahoney, J. Am. Chem. Soc. 86, 2653 (1964)
66. E.K. Euranto, A.L. Moisio, Suomen Kemistilehti 37B, 92 (1964)
67. R.P. Bell, G.A. Wright, Trans. Faraday Soc. 59, 1377 (1961)
68. J.D.R. Thomas, H.B. Watson. J. Chem. Soc. 3958 (1956)