New insights into the interconversion mechanism between phenol and its isomers

Journal of Molecular Structure: THEOCHEM

Volumn 767, Issue 1-3, 2006, Pages 11-18

  Gómez, Isabel ^a   Rodríguez, Elena ^a   Reguero, Mar ^a  

^a UNIVERSITAT ROVIRA I VIRGILI   (Spain)

Author keywords

Bond dissociation enthalpy; CASSCF CASPT2 calculations; Phenol tautomerization

Indexed keywords

EID: 33748594445     PISSN: 01661280     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.theochem.2006.03.034     Document Type: Article

References (63)

1. Su C., Lin C., Wu C., and Lien M. J. Phys. Chem. A 103 (1999) 3289
2. Wright J.S., Johnson E.R., and DiLabio G.A. J. Am. Chem. Soc. 123 (2001) 1173
3. Halliwell B., and Gutteridge J.M.C. Free Radicals in Biology and Medicine. second ed. (1989), Oxford University Press, Oxford
4. Tee O.S., and Iyengar N.R. J. Am. Chem. Soc. 107 (1985) 455
5. C. Horn, K. Roy, P. Frank, T. Just, Shock-Tube Study on the High-Temperature Pyrolisis of Phenol, 27th Symposium (International) on Combustion, University of Colorado at Boulder, 1998.
6. Ciprés R., and Bettens B. Tetrahedron 30 (1974) 1253
7. Hart H. Chem. Rev. 79 (1979) 515
8. Rappoport Z. The Chemistry of Enols (1990), Wiley, UK
9. Alagona G., Desmeules P., Ghio C., and Kollman P. J. Am. Chem. Soc. 106 (1984) 3623
10. Hupe J.D. New Comprehensive Biochemistry (1984), Elsevier, Amsterdam
11. Capon B., Guo B.Z., Kowk F.C., Siddhanta A.K., and Zukko C. Acc. Chem. Res. 21 (1988) 135
12. Jonson W.P., Gholamhossein H., and Whitman C.P. J. Am. Chem. Soc. 114 (1992) 11001
13. Capponi M., Gut I., and Wirz J. Angew. Chem. Int. Ed. Engl. 25 (1986) 344
14. Shiner C.S., Vorndam P.E., and Kass S.R. J. Am. Chem. Soc. 108 (1986) 5699
15. Santoro D., and Louw R. J. Chem. Soc. Perkin Trans. 2 (2001) 645
16. Gadosy T.A., and McClelland R.A. J. Mol. Struct. (Theochem) 369 (1996) 1
17. Pérez P., and Toro-Labbé A. J. Phys. Chem. A 104 (2000) 1557
18. Zhu L., and Bozzelli J.W. J. Phys. Chem. A 107 (2003) 3696
19. Bordwell F.G., and Cheng J. J. Am. Chem. Soc. 113 (1991) 1736
20. II Hoke S.H., Yang S.S., Cooks R.G., Hrovat D.A., and Borden W.T. J. Am. Chem. Soc. 116 (1994) 4888
21. Bizarro M.M., Costa Cabral B.J., Borges dos Santos R.M., and Martinho J.A. Pure Appl. Chem. 71 (1999) 1249
22. Wu Y., and Lai D.K.W. J. Org. Chem. 61 (1996) 7904
23. Himo F., Eriksson L.A., Blomberg M.R.A., and Siegbahn P.E.M. Int. J. Quantum Chem. 76 (2000) 714
24. Chandra A.K., and Uchimaru T. Int. J. Mol. Sci. 3 (2002) 407
25. Romero M.L., and Méndez F. J. Phys. Chem. A 107 (2003) 5874
26. Borges dos Santos R.M., and Martinho J.A. J. Phys. Chem. Ref. Data 27 (1998) 707
27. Blanksby S.J., and Ellison G.B. Acc. Chem. Res. 36 (2003) 255
28. Cabral do Couto P., Guedes R.C., Costa Cabral B.J., and Martinho Simões J.A. Int. J. Quantum Chem. 86 (2002) 297
29. Mulder P., Korth H.-G., Pratt D.A., DiLabio G.A., Valgimigli L., Pedulli G.F., and Ingold K.U. J. Phys. Chem. A 109 (2005) 2647
30. Head-Gordon M., and Pople J.A. J. Phys. Chem. 97 (1993) 1147
31. Hehre W.J., Radom L., Schleyer P.V.R., and Pople J.A. Ab-Initio Molecular Orbital Theory (1986), Wiley, New York p. 365
32. Quade C.R. J. Chem. Phys. 48 (1968) 5490
33. Zierkiewicz W., Michalska D., and Hobza P. Chem. Phys. Lett. 386 (2004) 95
34. For a review, see:. Roos B.-.O. Adv. Chem. Phys. 69 (1987) 399
35. Hariharan P.C., and Pople J.A. Theor. Chim. Acta 28 (1973) 213
36. Schlegel H.B. J. Comput. Chem. 3 (1982) 214
37. Bofill J.M. J. Comput. Chem. 15 (1994) 1
38. 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 B.04), Gaussian, Inc., Wallingford, CT, 2003.
39. Fukui K. Acc. Chem. Res. 14 (1981) 363
40. Schmidt M.W., Gordon M.S., and Dupuis M. J. Am. Chem. Soc. 107 (1985) 2585
41. Gonzalez C., and Schlegel B. J. Chem. Phys. 90 (1989) 2154
42. Gonzalez C., and Schlegel B. J. Phys. Chem. 94 (1990) 5523
43. Anderson K., Malmqvist P.-A., Roos B.O., Sadlej A.J., and Wolinski K. J. Phys. Chem. 94 (1990) 5483
44. Anderson K., Malmqvist P.-A., and Roos B.O. J. Chem. Phys. 96 (1992) 1218
45. K. Andersson, M. Barysz, A. Bernhardsson, M. R.A. Blomberg, Y. Carissan, D.L. Cooper, M. Cossi, M.P. Fülscher, L. Gagliardi, C. de Graaf, B.A. Hess, D. Hagberg, G. Karlström, R. Lindh, P.-Å. Malmqvist, T. Nakajima, P. Neogrády, J. Olsen, J. Raab, B.O. Roos, U. Ryde, B. Schimmelpfennig, M. Schütz, L. Seijo, L. Serrano-Andrés, P.E.M. Siegbahn, J. Stålring, T. Thorsteinsson, V. Veryazov, P.-O. Widmark, MOLCAS version 5.4, Lund University, Sweden, 2003.
46. Dunning Jr. T.H. J. Chem. Phys. 90 (1989) 1007
47. Kendall R.A., Dunning Jr. T.H., and Harrison R.J. J. Chem. Phys. 96 (1992) 6769
48. DeFrees D.J., and McLean A.D. J. Chem. Phys. 82 (1985) 333
49. Curtiss L.A., Raghavachari K., Trucks W.G., and Pople L.A. J. Chem. Phys. 94 (1991) 7221
50. Anderson K. Theor. Chim. Acta 91 (1995) 31
51. Le H.T., Flammang R., Gerbaux P., Bouchoux G., and Nguyen M.T. J. Phys. Chem. A 105 (2001) 11582
52. Zimmerman H.E., Sebek P., and Zhu Z. J. Am. Chem. Soc. 120 (1998) 8549
53. Matsuura T., Meng J.B., Ito Y., Irie M., and Fukuyama K. Tetrahedron 43 (1987) 2451
54. Fisch M.H., and Richards J.H. J. Am. Chem. Soc. 90 (1968) 1547
55. Dauben W.G., and Hecht S. J. Org. Chem. 63 (1998) 6102
56. Gómez I., Olivella S., Reguero M., Riera A., and Sole A. J. Am. Chem. Soc. 124 (2002) 15375
57. Osamura Y., Borden W.T., and Morokuma K. J. Am. Chem. Soc. 106 (1984) 5112
58. Ichimira A.S., Lathi P.M., and Matlin A.R. J. Am. Chem. Soc. 112 (1990) 2868
59. Powell H.K., and Borden W.T. J. Org. Chem. 60 (1990) 2654
60. Lim D., Hrovat D.A., Borden W.T., and Jorgensen W.L. J. Am. Chem. Soc. 116 (1994) 3494
61. Hrovat D.A., Rauk A., Sorensen T.S., Powell H.K., and Borden W.T. J. Am. Chem. Soc. 118 (1996) 4159
62. Matlin A.R., Lathi P.M., Appella D., Straumanis A., Lin S., Patel H., Jin K., Schrieber K.P., Pauls J., and Raulerson P. J. Am. Chem. Soc. 121 (1999) 2164
63. Hammond G.S. J. Am. Chem. Soc. 77 (1955) 334