Study of N-H, O-H, and S-H bond dissociation enthalpies and ionization potentials of substituted anilines, phenols, and thiophenols

Journal of Molecular Structure: THEOCHEM

Volumn 758, Issue 2-3, 2006, Pages 149-159

  Klein, Erik ^a   Lukeš, Vladimír ^a   Cibulková, Zuzana ^a   Polovková, Júlia ^a  

^a SLOVAK UNIVERSITY OF TECHNOLOGY   (Slovakia)

Author keywords

Aniline; BDE; Bond dissociation enthalpy; Ionization potential; Phenol; Thiophenol

Indexed keywords

EID: 31944452720     PISSN: 01661280     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.theochem.2005.10.015     Document Type: Article

References (47)

1. F. Gugumus Oxidation Inhibition in Organic Materials vol. 1 1990 CRC Press Boca Raton, FL
2. Q. Zhu, X.M. Zhang, and A.J. Fry Polym. Degrad. Stab. 57 1997 43
3. J.F. Rabek Photostabilization of Polymers 1990 Elsevier New York
4. J. Pospíšil, J. Horák, J. Pilar, N.C. Billingham, H. Zweifel, and S. Nešpůrek Polym. Degrad. Stab. 82 2003 145
5. R. Wolf, and B.L. Kaul Plastics, Additives Ullmann's Encyclopedia of Industrial Chemistry 1992 VCH Weinheim
6. M. Mandalo, A.M. Graña, and R.A. Mosquera Chem. Phys. Lett. 400 2004 169
7. E.T. Denisov Polym. Degrad. Stab. 49 1995 71
8. D.A. Pratt, G.A. DiLabio, G. Brigati, G.F. Pedulli, and L. Valgimigli J. Am. Chem. Soc. 123 2001 4625
9. G.W. Burton, T. Doba, E.J. Gabe, L. Hughes, F.L. Lee, L. Prasad, and K.U. Ingold J. Am. Chem. Soc. 107 1985 7053
10. J.S. Wright, E.R. Johnson, and G.A. DiLabio J. Am. Chem. Soc. 123 2001 1173
11. R.J. Berry, A.L. Wilson, and M. Schwartz J. Mol. Struct. (Theochem) 496 2000 121
12. K. Wei, S.-W. Luo, Y. Fu, and Q.-X. Guo J. Mol. Struct. (Theochem) 712 2004 197
13. D.A. Pratt, G.A. DiLabio, L. Valgimigli, G.F. Pedulli, and K.U. Ingold J. Am. Chem. Soc. 124 2002 11085
14. F.G. Bordwell, and J.-P. Cheng J. Am. Chem. Soc. 113 1991 1736
15. F.G. Bordwell, X.M. Zhang, and J.-P. Cheng J. Org. Chem. 58 1993 6410
16. M. Jonsson, J. Lind, T.E. Eriksen, and G. Merenyi J. Am. Chem. Soc. 116 1994 1423
17. P.A. MacFaul, D.D.M. Wayner, and K.U. Ingold J. Org. Chem. 62 1997 3413
18. G.A. DiLabio, D.A. Pratt, A.D. LoFaro, and J.S. Wright J. Phys. Chem. A 103 1999 1653
19. F.G. Bordwell, X.-M. Zhang, A.V. Satish, and J.-P. Cheng J. Am. Chem. Soc. 119 1997 9125
20. D.A. Pratt, G.A. DiLabio, P. Mulder, and K.U. Ingold Acc. Chem. Res. 37 2004 334
21. M.J.S. Dewar, and W. Thiel J. Am. Chem. Soc. 99 1977 4899
22. M.J.S. Dewar, E.G. Zoebisch, E.F. Healy, and J.J.P. Stewart J. Am. Chem. Soc. 107 1985 3902
23. J.J.P. Stewart J. Comput. Chem. 10 1989 221
24. J.J.P. Stewart J. Comput. Aided. Mol. Des. 4 1990 1
25. C. Hansch, A. Leo, and R.W. Taft Chem. Rev. 91 1991 165
26. 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, 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 A.1, Gaussian, Inc., Pittsburgh, PA, 2003.
27. V.K. Potapov, I.E. Kardash, V.V. Sorokin, S.A. Sokolov, and T.I. Evlasheva Khim. Vys. Energ. 6 1972 392
28. A. Buchs Helv. Chim. Acta 53 1970 2026
29. P. Brown Org. Mass Spectrom. 3 1970 639
30. L. Szepes, G. Distefano, and S. Pignataro Ann. Chim. 64 1974 159
31. J.F. Gal, S. Geribaldi, G. Pfister-Guillouzo, and D.G. Morris J. Chem. Soc. Perkin Trans. 2 1985 103
32. M. Takahashi, H. Ozeki, and K. Kimura J. Chem. Phys. 96 1992 6399
33. P.G. Farrell, and J. Newton Tetrahedron Lett. 45 1966 5517
34. A.K. Chandra, and T. Uchimaru Int. J. Mol. Sci. 3 2002 407
35. J.D. Cox, and G. Pilcher Thermochemistry of Organic and Organometallic Compounds 1970 Academic Press New York
36. R.J. Lipert, and S.D. Colson J. Chem. Phys. 92 1990 3240
37. P. Brown Org. Mass Spectrom. 4 1970 519
38. E.T.M. Selim, M.A. Fahmey, and H.S. Ghonime Indian J. Phys. 65 1991 171
39. A.D. Baker, D.P. May, and D.W. Turner J. Chem. Soc. B 1968 22
40. M.C.R. Cockett, M. Takahashi, K. Okuyama, and K. Kimura Chem. Phys. Lett. 187 1991 250
41. E.J. McAlduff, and D.L. Bunbury J. Electron. Spectrosc. Relat. Phenom. 17 1979 81
42. A. Foffani, S. Pignataro, B. Cantone, and F. Grasso Z. Phys. Chem. (Frankfurt) 42 1964 221
43. T. Kobayashi, and S. Nagakura J. Electron. Spectrosc. Relat. Phenom. 6 1975 421
44. J.D. Faulk, R.C. Dunbar, and C. Lifshitz J. Am. Chem. Soc. 112 1990 7893
45. P.S. Dewar, E. Ernstbrunner, J.R. Gilmore, M. Godfrey, and J.M. Mellor Tetrahedron 30 1974 2455
46. Y. Kuwae, and M. Kamachi Bull. Chem. Soc. Jpn 62 1989 2474
47. E. Klein, Z. Cibulková, and V. Lukeš Polym. Degrad. Stab. 88 2005 548