Solvent Effects on the Energetics of the Phenol O-H Bond: Differential Solvation of Phenol and Phenoxy Radical in Benzene and Acetonitrile

Journal of Physical Chemistry A

Volumn 107, Issue 43, 2003, Pages 9197-9207

  Guedes, R C ^a,b   Coutinho, Kaline ^c   Costa Cabrai, B J ^a,b   Canuto, Sylvio ^d   Correia, C F ^a   Borges dos Santos, R M ^e   Martinho Simoes J A ^a  

^a UNIVERSITY OF LISBON   (Portugal)

^b UNIVERSITY OF LISBON   (Portugal)

^c UNIVERSIDADE DE MOGI DAS CRUZES   (Brazil)

^d UNIVERSITY OF SÃO PAULO   (Brazil)

^e UNIVERSITY OF ALGARVE   (Portugal)

Author keywords

[No Author keywords available]

Indexed keywords

ACETONITRILE; BENZENE; COMPUTER SIMULATION; ENTHALPY; FREE RADICALS; HYDROGEN BONDS; ORGANIC SOLVENTS; SOLUBILITY;

SOLUTES;

PHENOLS;

EID: 0242583947     PISSN: 10895639     EISSN: None     Source Type: Journal    
DOI: 10.1021/jp035912c     Document Type: Article

References (62)

1. Platz, J.; Nielsen, O. J.; Wallington, T. J.; Ball, J. C.; Hurley, M. D. ; Straccia, A. M.; Schneider, W. F. J. Phys. Chem. A 1998, 102, 7964.
2. Sibener, S. J.; Buss, R. J.; Casavecchia, P.; Hirooka, T.; Lee, Y. T. J. Chem. Phys. 1980, 72, 4341.
3. Liu, R.; Morokuma, K.; Mebel, A. M.; Lin, M. C. J. Phys. Chem. 1996, 100, 9314.
4. Lin, C.-Y.; Lin, M. C. J. Phys. Chem. 1986, 90, 425.
5. Weaver, E. C. Annu. Rev. Plant. Physiol. 1968, 19, 283.
6. Itoh, S.; Taki, M.; Fukuzumi, S. Coord. Chem. Rev. 2000, 198, 3.
7. Kagan, V. E.; Tyurina, Y. Y. Ann. N. Y. Acad. Sci. 1998, 854.
8. Borges dos Santos, R. M.; Martinho Simões, J. A. J. Phys. Chem. Ref. Data 1998, 27, 707.
9. Couto, P. C.; Guedes, R. C.; Cabrai, B. J. C.; Martinho Simões, J. A. Int. J. Quantum Chem. 2002, 56, 297 and references therein.
10. Correia, C. F.; Guedes, R. C.; Borges dos Santos, Cabral, B. J. C.; Martinho Simões, J. A. J. Phys. Chem. A, submitted for publication, 2003.
11. Wayner, D. D. M.; Lusztyk, E.; Pagé, D.; Ingold, K. U.; Mulder, P.; Laarhoven, L. J. J.; Aldrich, H. S. J. Am. Chem. Soc. 1995, 117, 8737.
12. See, for example, ref 11 and references therein.
13. (a) Drago, R. S.; Dadmun, A. P.; Vogel, G. C. Inorg. Chem. 1993, 32, 2473.
14. (b) Vogel, G. C.; Drago, R. S. J. Chem. Educ. 1996, 73, 701-707.
15. (c) Drago, R. S. Applications of Electrostatic-Covalent Models in Chemistry; Surfside: Gainesville, FL, 1994.
16. Borges dos Santos, R. M.; Muralha, V. S. F.; Correia, C. F.; Martinho Simões, J. A. J. Am. Chem. Soc. 2001, 123, 12670.
17. Borges dos Santos, R. M.; Muralha, V. S. F.; Correia, C. F.; Guedes, R. C.; Cabral, B. J. C.; Martinho Simões, J. A. J. Phys. Chem. A 2002, 106. 9883.
18. Fernandez, J. A.; Yao, J.; Bernstein, E. R. J. Chem. Phys. 1997, 107, 3363.
19. Fernandez, J. A.; Yao, J.; Bernstein, E. R. J. Chem. Phys. 1999, 110, 5159.
20. Yao, J.; Fernandez, J. A.; Bernstein, E. R. J. Chem. Phys. 1999, 110, 5174.
21. Fernandez, J. A.; Yao, J.; Bernstein, E. R. J. Chem. Phys. 1999, 110, 5183.
22. Bray, J. A.; Bernstein, E. R. J. Phys. Chem. A 1999, 103, 2214.
23. Chipman, D. M. J. Phys. Chem. A 1999, 103, 11181.
24. Guedes, R. C.; Cabral, B. J. C.; Martinho Simões, J. A.; Diogo, H. P. J. Phys. Chem. A 2000, 104, 6062.
25. Guedes, R. C.; Coutinho, K.; Cabral, B. J. C.; Canuto, S. J. Phys. Chem. B 2003, 107, 4304.
26. Kirkwood, J. G. J. Chem. Phys. 1935, 3, 300.
27. Zwanzig, R. W. J. Chem. Phys. 1954, 22, 1420.
28. Jorgensen, W. L.; Ravimohan, C. J. Chem. Phys. 1985, 83, 3050.
29. Straatsma, T. P.; McCammon, J. A. J. Chem. Phys. 1989, 90, 3300.
30. Becke, A. D. J. Chem. Phys. 1993, 95, 5648.
31. Lee, C.; Yang, W.; Parr, R. G. Phys. Rev. B 1988, 37, 785.
32. Petersson, G. A.; Bennett, A.; Tensfeldt, T. G.; Al-Laham, M. A.; Shirley, W. A.; Mantzaris, J. J. Chem. Phys. 1988, 89, 2193.
33. Krishnan, R.; Binkley, J. S.; Seeger, R.; Pople, J. A. J. Chem. Phys. 1980, 72, 650.
34. Boys, S. F.; Bernardi, F. Mol. Phys. 1970, 19, 553.
35. Xantheas, S. S. J. Chem. Phys. 1996, 104, 8821.
36. Frisch, M. J.; Trucks, G. W.; Schlegel, H. B.; Scuseria, G. E.; Robb, M. A.; Cheeseman, J. R.; Zakrzewski, V. G.; Montgomery, J. A., Jr.; Stratmann, R. E.; Burant, J. C.; Dapprich, S.; Millam, J. M.; Daniels, A. D.; Kudin, K. N.; Strain, M. C.; Farkas, O.; Tomasi, J.; Barone, V.; Cossi, M.; Cammi, R.; Mennucci, B.; Pomelli, C.; Adamo, C.; Clifford, S.; Ochterski, J.; Petersson, G. A.; Ayala, P. Y.; Cui, Q.; Morokuma, K.; Malick, D. K.; Rabuck, A. D.; Raghavachari, K.; Foresman, J. B.; Cioslowski, J.; Ortiz, J. V.; Stefanov, B. B.; Liu, G.; Liashenko, A.; Piskorz, P.; Komaromi, L; Gomperts, R.; Martin, R. L.; Fox, D. J.; Keith, T.; Al-Laham, M. A.; Peng, C. Y.; Nanayakkara, A.; Gonzalez, C.; Challacombe, M.; Gill, P. M. W.; Johnson, B. G.; Chen, W.; Wong, M. W.; Andres, J. L.; Head-Gordon, M.; Replogle, E. S.; Pople, J. A. Gaussian 98, revision A.7; Gaussian, Inc.: Pittsburgh, PA, 1998.
37. Frenkel, D.; Smit, B. Understanding Molecular Simulation; Academic Press: San Diego, CA, 1996. Allen, M. P.; Tildesley, D. J. Computer Simulation of Liquids; Clarendon: New York, 1987.
38. Frenkel, D.; Smit, B. Understanding Molecular Simulation; Academic Press: San Diego, CA, 1996. Allen, M. P.; Tildesley, D. J. Computer Simulation of Liquids; Clarendon: New York, 1987.
39. Jorgensen, W. L.; Nguyen, T. B. J. Comput. Chem. 1993, 14, 195.
40. Jorgensen, W. L.; Severance, D. L. J. Am. Chem. Soc. 1990, 112, 4768.
41. Böhm, H. J.; McDonald, I. R.; Madden, P. A. Mol. Phys. 1983, 49, 347.
42. Mooney, D. A.; Müller-Plathe, F.; Kremer, K. Chem. Phys. Lett. 1998, 294, 135.
43. Singh, U. C.; Kollman, P. A. J. Comput. Chem. 1984, 5, 129.
44. Besler, B. H.; Merz, K. M., Jr.; Kollman, P. A. J. Comput. Chem. 1990, 11, 431.
45. McClenman, A. L. Tables of Experimental Dipole Moments; Freeman: San Francisco, CA, 1963; Vol. 1.
46. Coutinho, K.; Canuto, S. DICE: A General Monte Carlo Program for Liquid Simulation; University of São Paulo: São Paulo, Brazil, 2000.
47. Borges dos Santos, R. M.; Lagoa, A. L. C.; Martinho Simões, J. A. J. Chem. Thermodyn. 1999, 31, 1483.
48. Diogo, H. P.; Minas da Piedade, M. E.; Martinho Simões, J. A.; Teixeira, C. J. Organomet. Chem. 2001, 632, 188 and references therein.
49. Diogo, H. P.; Minas da Piedade, M. E.; Martinho Simões, J. A.; Nagano, Y. J. Chem. Thermodyn. 1995, 27, 597.
50. Kryachko, E. S.; Nguyen, M. T. J. Phys. Chem. A 2002, 106, 4267.
51. Levchuk, V. N.; Sheykhet, I. I.; Simkin, B. Ya. Chem. Phys. Lett. 1991, 185, 339.
52. Lazaridis, T. J. Phys. Chem. B 2000, 104, 4964.
53. Pedley, J. B. Thermodynamic Data and Structures of Organic Compounds; Thermodynamics Research Center: College Station, TX, 1994; Vol. 1.
54. Parker, V. D. J. Am. Chem. Soc. 1992, 114, 7458; 1993, 115, 1201.
55. Parker, V. D. J. Am. Chem. Soc. 1992, 114, 7458; 1993, 115, 1201.
56. See, for example: Irikura, K. K., Frurip, D. J., Eds. Computational Thermochemistry. Prediction and Estimation of Molecular Thermodynamics; ACS Symposium Series 677; American Chemical Society: Washington, DC, 1998.
57. Coutinho, K.; Canuto, S.; Zerner, M. C. J. Chem. Phys. 2000, 112, 9874.
58. Canuto, S.; Coutinho, K. Int. J. Quantum Chem. 2000, 77, 192.
59. Coutinho, K.; Canuto, S. J. Chem. Phys. 2000, 113, 9132.
60. -1. See ref 23.
61. Katritzky, A. R.; Zerner, M. C.; Karelson N. M. J. Am. Chem. Soc. 1986, 108, 7213.
62. Malaspina, T.; Coutinho, K.; Canuto, S. J. Chem. Phys. 2002, 117, 1692.