Triadic analysis of substituent effects - Gas-phase acidity of para-substituted phenols

Tetrahedron

Volumn 62, Issue 14, 2006, Pages 3402-3411

  Vianello, Robert ^a   Maksić, Zvonimir B ^a  

^a RUDER BO KOVI INSTITUTE   (Croatia)

Author keywords

Acidity; Phenol; Substituent effect; Superacidifiers; Triadic analysis

Indexed keywords

PHENOL;

ACIDITY; ARTICLE; ELECTRON; GAS; LABORATORY TEST; PRIORITY JOURNAL;

EID: 33644901358     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tet.2006.01.049     Document Type: Article

References (53)

1. O. Exner, and T.M. Krygowski Chem. Soc. Rev. 25 1996 71 75
2. T.M. Krygowski, and B.T. Stepień Chem. Rev. 105 2005 3482 3512
3. L.P. Hammett Physical Organic Chemistry 1940 McGraw-Hill New York
4. C. Hansch, and A. Leo Exploring QSAR: Fundamentals and Applications in Chemistry and Biology 1995 American Chemical Society Washington, DC
5. H.H. Jaffé J. Am. Chem. Soc. 75 1953 191 195
6. Y. Yukawa, and Y. Tsuno Bull. Chem. Soc. Jpn. 32 1959 971 981
7. M. Charton Prog. Phys. Org. Chem. 13 1981 119 251
8. R.W. Taft M.S. Newman Steric Effects in Organic Chemistry 1956 Wiley New York
9. G.P. Ford, A.R. Katritzky, and R.D. Topson N.B. Chapman J. Shorter Correlation Analysis in Chemistry: Recent Advances 1978 Plenum New York
10. O. Exner Correlation Analysis of Chemical Data 1988 Plenum London
11. R.W. Taft, and R.D. Topson Prog. Phys. Org. Chem. 16 1987 1 83
12. C. Hansch, A. Leo, and R.W. Taft Chem. Rev. 91 1991 165 195
13. R.D. Topsom Prog. Phys. Org. Chem. 16 1987 125 191
14. A. Pross, L. Radom, and R.W. Taft J. Org. Chem. 45 1980 818 826
15. P. George, M. Trachtman, C.W. Bock, and A.M. Brett Tetrahedron 32 1976 317 323
16. P. George, M. Trachtman, C.W. Bock, and A.M. Brett J. Chem. Soc., Perkin Trans. 2 2 1976 1222 1227
17. O. Exner, and S. Böhm J. Org. Chem. 67 2002 6320 6327
18. R.F. Hudson, and G. Klopman J. Chem. Soc. 1964 5 15
19. R. Karaman, J.-T. Huang, and J.L. Fry J. Comput. Chem. 11 1990 1009 1016
20. M. Haeberlein, and T. Brinck J. Phys. Chem. 100 1996 10116 10120
21. F. Méndez, M.L. Romero, F. De Proft, and P. Geerlings J. Org. Chem. 63 1998 5774 5778
22. K.C. Gross, and P.G. Seybold Int. J. Quantum Chem. 85 2001 569 579 and references therein
23. M.L. Romero, and F. Méndez J. Phys. Chem. A 107 2003 4526 4530
24. L.A. Angel, and K.M. Ervin J. Phys. Chem. A 108 2004 8346 8352
25. J.B. Barbour, and J.M. Karty J. Phys. Org. Chem. 18 2005 210 216
26. T.M. Krygowski, B.T. Stepien, M.K. Cyrański, and K. Ejsmont J. Phys. Org. Chem. 18 2005 886 891
27. Z.B. Maksić, and R. Vianello J. Phys. Chem. A 106 2002 419 430
28. Z.B. Maksić, and R. Vianello ChemPhysChem 3 2002 696 700
29. R. Vianello, and Z.B. Maksić J. Phys. Org. Chem. 18 2005 699 705
30. C.A. Deakyne Int. J. Mass Spectrom. 227 2003 601 616
31. M. Alcamí, O. Mó, and M. Yáñez Mass Spectrom. Rev. 20 2001 195 245
32. M. Alcamí, O. Mó, and M. Yáñez J. Phys. Org. Chem. 15 2002 174 186
33. R. Vianello, J.F. Liebman, and Z.B. Maksić Chem. Eur. J. 10 2004 5751 5760
34. 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.; Baboul, A. G.; Stefanov, B. B.; Liu, G.; Liashenko, A.; Piskorz, P.; Komaromi, I.; 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.10), Gaussian, Inc.: Pittsburgh PA, 1998.
35. R. Vianello, and Z.B. Maksić Eur. J. Org. Chem. 2005 3571 3580
36. R. Vianello, and Z.B. Maksić Chem. Commun. 2005 3412 3414
37. R. Vianello, and Z.B. Maksić Tetrahedron 61 2005 9381 9390
38. L.M. Yagupolskii, V.F. Bystrov, and E.Z. Utyanskaya Dokl. Akad. Nauk. USSR 135 1996 377
39. L.M. Yagupolskii, A.Yo. Il'chenko, and N.B. Kontradenko Usp. Khim. 43 1974 64 94
40. W.A. Sheppard J. Am. Chem. Soc. 85 1963 1314 1318
41. W.A. Sheppard, and R.W. Taft J. Am. Chem. Soc. 94 1972 1919 1923
42. A.I. Koppel, R.W. Taft, F. Anvia, S.-Z. Zhu, L.Q. Hu, K.-S. Sung, D.D. Desmarteau, L.M. Yagupolskii, V.M. Vlasov, R. Notario, and P.C. Maria J. Am. Chem. Soc. 116 1994 3047 3057
43. I.A. Koppel, J. Koppel, I.V. Leito, I. Koppel, M. Mishima, and L.M. Yagupolskii J. Chem. Soc., Perkin Trans. 2 2001 229 232
44. L.M. Yagupolskii, V.N. Petrick, N.V. Kontradenko, L. Sooväli, I. Kaljurand, I.V. Leito, and A.I. Koppel J. Chem. Soc., Perkin Trans. 2 2002 1950 1955
45. I.A. Koppel, P. Burk, I. Koppel, and I. Leito J. Am. Chem. Soc. 124 2002 5594 5600
46. R. Goumont, E. Kizilian, E. Buncel, and F. Terrier Org. Biomol. Chem. 1 2003 1741 1748
47. F. Terrier, E. Magnier, E. Kizilian, C. Wakselman, and E. Buncel J. Am. Chem. Soc. 127 2005 5563 5571
48. R.S. Mulliken J. Chem. Phys. 23 1995 1833 1840
49. U.C. Singh, and P.A. Kollman J. Comput. Chem. 5 1984 129 145
50. B.H. Besler, K.M.J. Merz, and P.A. Kollman J. Comput. Chem. 11 1990 431 439
51. A.E. Reed, R.B. Weinstock, and F. Weinhold J. Chem. Phys. 83 1985 735 746
52. M. Haeberlein, J.S. Murray, T. Brinck, and P.A. Politzer Can. J. Chem. 70 1992 2209 2214
53. P. Sjoberg, J.S. Murray, T. Brinck, and P.A. Politzer Can. J. Chem. 68 1990 1440 1443