A theoretical study of the additivity of proton affinities in aromatics: Polysubstituted benzenes

Chemistry - A European Journal

Volumn 2, Issue 10, 1996, Pages 1251-1257

  Eckert Maksić, Mirjana ^b,c   Klessinger, Martin ^a   Maksić, Zvonimir B ^b,c  

^a UNIVERSITY OF MÜNSTER   (Germany)

^b RUDER BO KOVI INSTITUTE   (Croatia)

^c UNIVERSITY OF ZAGREB   (Croatia)

Author keywords

Ab initio calculations; Benzenes; Electrophilic substitutions; Proton affinities; QSAR

Indexed keywords

AB INITIO CALCULATIONS; ADDITIVITY RULES; BENZENE RING; ELECTROPHILIC SUBSTITUTIONS; PROTON AFFINITY; QSAR; THEORETICAL MODELING; THEORETICAL STUDY;

PROTONS;

BENZENE;

EID: 0000713174     PISSN: 09476539     EISSN: 15213765     Source Type: Journal    
DOI: 10.1002/chem.19960021011     Document Type: Article

References (32)

1. a) E. M. Arnett, Acc. Chem. Res. 1973, 7, 404;
2. b) M. Meot-Ner (Mautner), Acc. Chem. Res. 1984, 17, 186;
3. F. Cacace, Acc. Chem. Res. 1988, 21, 215.
4. a) S. G. Lias, J. F. Liebman, R. D. Levin, J. Phys. Chem. Ref. Data 1984, 13, 695;
5. b) G. A. Harrison, Chemical Ionization Mass Spectrometry, CRC, Boca Raton, 1989.
6. D. H. Aue, M. T. Bowers in Gas Phase Ion Chemistry, Vol. 2 (Ed.: M. T. Bowers), Academic Press, New York, 1979.
7. R. Taylor, Electrophilic Aromatic Substitution, Wiley, Chichester, 1990.
8. M. Eckert-Maksić, Z. B. Maksić, M. Klessinger, Int. J. Quant. Chem. 1994, 49, 383;
9. J. Chem. Soc. Perkin Trans. 2, 1994, 285.
10. B. J. Smith, L. Radom, J. Am. Chem. Soc. 1993, 115, 4885.
11. J. E. Szulejko, T. B. McMahon, J. Am. Chem. Soc. 1993, 115, 7839.
12. L. A. Curtiss, K. Raghavachari, G. W. Trucks, J. A. Pople, J. Chem. Phys. 1991, 94, 7221.
13. M. Eckert-Maksić, M. Klessinger, Z. B. Maksić, Chem. Phys. Lett. 1995, 232, 472.
14. M. Eckert-Maksić, M. Klessinger, Z. B. Maksić, J. Phys. Org. Chem. 1995, 8, 435.
15. J. W. Hehre, L. Radom, P. v. R. Schleyer, J. A. Pople, Ab Initio Molecular Orbital Theory, Wiley-Interscience, New York, 1986, and references cited therein.
16. a) GAUSSIAN 92, Revision B, M. J. Frisch, G. W. Trucks, M. Head-Gordon, P. M. W. Gill, M. W. Wong, J. B. Foresman, B. G. Johnson, H. B. Schlegel, M. A. Robb, E. S. Replogle, R. Gomperts, J. L. Andres, K. Raghavachari, J. S. Binkley, C. Gonzalez, R. L. Martin, D. J. Fox, D. J. Defrees, J. Baker, J. J. P. Stewart, J. A. Pople, Gaussian, Pittsburgh PA, 1992;
17. b) GAUSSIAN 94, Revision B.2, M. J. Frisch, G. W. Trucks, H. B. Schlegel, P. M. W. Gill, B. G. Johnson, M. A. Robb, J. R. Cheeseman, T. Keith, G. A. Petersson, J. A. Montgomery, K. Raghavachari, M. A. Al-Laham, V. G. Zakrzewski, J. V. Ortiz, J. B. Foresman, J. Cioslowski, B. B. Stefanov, A. Nanavakkara, M. Challacombe, C. Y. Peng, P. A. Avala, W. Chen, M. W. Wong, J. L. Andres, E. S. Replogle, R. Gomperts, R. L. Martin, D. J. Fox, J. S. Binkley, D. J. Defrees, J. Baker, J. P. Stewart, M. Head-Gordon, C. Gonzalez, J. A. Pople, Gaussian, Pittsburgh PA, 1995.
18. P. George, M. Trachtmann, C. W. Bock, A. M. Brett, Tetrahedron 1976, 32, 313;
19. J. Chem. Soc. Perkin Trans. 2 1976, 1222.
20. G. W. Wheland, J. Am. Chem. Soc. 1942, 64, 900.
21. G. S. Hammond, J. Am. Chem. Soc. 1955, 77, 334.
22. J. L. Devlin, III, J. F. Wolf, R. W. Taft, W. J. Hehre, J. Am. Chem. Soc. 1976, 98, 1990.
23. A. Streitwieser, Jr., C. H. Heathcock, Introduction to Organic Chemistry, Ch. 29, McMillan, New York, 1976.
24. Y. K. Lau, P. Kebarle, J. Am. Chem. Soc. 1976, 98, 7452.
25. B. S. Freiser, R. L. Woodin, J. L. Beauchamp, J. Am. Chem. Soc. 1975, 97, 6893.
26. P. B. D. De la Mare, Tetrahedron 1959, 5, 107.
27. S. G. Lias, J. E. Bartmess, J. F. Liebman, J. L. Holmes, R. D. Levin, W. G. Mallard, J. Phys. Chem. Ref. Data, Suppl. 1 1988, 17.
28. Z. B. Maksić, M. Eckert-Maksić, M. Klessinger, Chem. Phys. Lett. 1996, in press.
29. H. C. Brown, J. D. Brady, J. Am. Chem. Soc. 1952, 74, 3570.
30. R. Walder, J. L. Franklin, Int. J. Mass. Spectr. Ion Phys. 1980, 36, 85.
31. G. A. Olah, Y. K. Mo in Carbonium Ions, Vol. 5 (Eds.: G. A. Olah, P. v. R. Schleyer), Wiley-Interscience, New York, 1976, p. 2135.
32. M. Eckert-Maksić, M. Hodošček, D. Kovaček, Z. B. Maksić, J. Mol. Struct. (Theochem), 1996, in press.