Interrelations between the mesomeric and electronegativity effects in Para-substituted derivatives of phenol/phenolate and aniline/anilide H-bonded complexes: A DFT-based computational study

Journal of Physical Chemistry A

Volumn 113, Issue 19, 2009, Pages 5800-5805

  Szatyłowicz, Halina ^a   Krygowski, Tadeusz M ^b   Jezierska, Aneta ^c,d   Panek, Jarosław J ^c  

^a WARSAW UNIVERSITY OF TECHNOLOGY   (Poland)

^b UNIVERSITY OF WARSAW   (Poland)

^c UNIVERSITY OF WROC AW   (Poland)

^d NATIONAL INSTITUTE OF CHEMISTRY   (Slovenia)

Author keywords

[No Author keywords available]

Indexed keywords

ARITHMETIC MEAN; CARBON ATOMS; COMPUTATIONAL STUDIES; ELECTONEGATIVITY; GEOMETRIC PARAMETER; H-BONDED COMPLEXES; NON EQUILIBRIUM; RESONANCE EFFECT; SUBSTITUENT EFFECT; VALENCE ANGLES; WALSH RULE;

ACIDS; CHEMICAL BONDS; ELECTRONEGATIVITY; RESONANCE;

ATOMS;

EID: 66149129186     PISSN: 10895639     EISSN: None     Source Type: Journal    
DOI: 10.1021/jp8109258     Document Type: Article

References (41)

1. (a) Walsh, A. D. Discuss. Faraday Soc. 1947, 2, 18-25.
2. (b) Bent, H. A. Chem. Rev. 1961, 61, 275-311.
3. (a) Kovaèevic, K.; Maksic, Z. B. J. Org. Chem. 1974, 39, 539-545.
4. (b) Maksic, Z. B.; Rubèic, A. J. Am. Chem. Soc. 1977, 99, 4233-4241.
5. (c) Maksic, Z. B. Comput. Math. Appl. 1986, 12, 697-723.
6. (a) Domenicano, A.; Vaciago, A.; Coulson, C. A. Acta Crystallogr. 1975, B31, 221-234.
7. (b) Domenicano, A.; Vaciago, A.; Coulson, C. A. Acta Crystallogr. 1975, B31, 1630-1641.
8. (c) Domenicano, A.; Murray-Rust, P. Tetrahedron Lett. 1979, 20, 2283-2296.
9. (d) Domenicano, A.; Murray-Rust, P.; Vaciago, A. Acta Crystallogr. 1983, B39, 457-468.
10. Korchowiec, J.; Nalewajski, R. F. Int. J. Quantum Chem. 1992, 44, 1027-1040.
11. (a) Huheey, J. Phys. Chem. 1965, 69, 3284-3291.
12. (b) Huheey, J. J. Phys. Chem. 1966, 70, 2086-2092.
13. Campanelli, A. R.; Domenicano, A.; Ramondo, F. J. Phys. Chem. A 2003, 107, 6429-6440.
14. Campanelli, A. R.; Domenicano, A.; Ramondo, F.; Hargittai, I. J. Phys. Chem. A 2004, 108, 4940-4948.
15. Zalewski, R. I. In Similarity Models in Organic Chemistry, Biochemistry and Related Fields; Zalewski, R. I., Krygowski, T. M., Shorter, J., Eds.; Elsevier: Amsterdam, The Netherlands, 1991; Chapter 9, p 453.
16. Iczkowski, R. P.; Margrave, J. L. J. Am Chem. Soc. 1961, 83, 3547-3551.
17. Woźniak, K.; Krygowski, T. M.; Kariuki, B.; Jones, W. J. Mol. Struct. 1991, 248, 331-343.
18. Krygowski, T. M.; Szatylowicz, H. J. Phys. Chem. A 2006, 110, 7232-7236.
19. Exner, O.; Krygowski, T. M. Chem. Soc. Rev. 1996, 25, 71-75.
20. Boese, R.; Blaser, D.; Krygowski, T. M. Struct. Chem. 1992, 3, 363-368.
21. Irle, S.; Krygowski, T. M.; Niu, J. E.; Schwarz, W. H. E. J. Org. Chem. 1995, 60, 6744-6755.
22. Hansch, C.; Leo, A.; Taft, R. W. Chem. Rev. 1991, 91, 165-195.
23. (a) Szatyłowicz, H.; Krygowski, T. M.; Zachara-Horeglad, J. E. J. Chem. Inf. Model. 2007, 47, 875-886.
24. (b) Krygowski, T. M.; Szatylowicz, H. Trends Org. Chem. 2006, 11, 37-53.
25. (a) Hohenberg, P.; Kohn, W. Phys. Rev. 1964, 136, B864-B871.
26. (b) Kohn, W.; Sham, L. J. Phys. Rev. 1965, 140, A1133-A1138.
27. (c) Stephens, P. J.; Devlin, F. J.; Chabalowski, C. R.; Frisch, M. J. J. Phys. Chem. 1994, 98, 11623-11627.
28. (a) Becke, A. D. J. Chem. Phys. 1993, 98, 1372-1377.
29. (b) Becke, A. D. J. Chem. Phys. 1993, 98, 5648-5652.
30. Lee, C.; Yang, W.; Parr, R G. Phys. Rev. B 1988, 37, 785-789.
31. Krishnan, R.; Binkley, J. S.; Seeger, R.; Pople, J. A. J. Chem. Phys. 1980, 72, 650-654.
32. Mulliken, R. S. J. Chem. Phys. 1955, 23, 1833-1840.
33. Frisch, M. J.; Trucks, G. W.; Schlegel, H. B.; Scuseria, G. E.; Robb, M. A.; Cheeseman, J. R.; Montgomery, J. A., Jr.; Vreven, T.; Kudin, K. N.; Burant, J. C.; Millam, J. M.; Iyengar, S. S.; Tomasi, J.; Barone, V.; Mennucci, B.; Cossi, M.; Scalmani, G.; Rega, N.; Petersson, G. A.; Nakatsuji, H.; Hada, M.; Ehara, M.; Toyota, K.; Fukuda, R.; Hasegawa, J.; Ishida, M.; Nakajima, T.; Honda, Y.; Kitao, O.; Nakai, H.; Klene, M.; Li, X.; Knox, J. E.; Hratchian, H. P.; Cross, J. B.; Bakken, V.; Adamo, C.; Jaramillo, J.; Gomperts, R.; Stratmann, R. E.; Yazyev, O.; Austin, A. J.; Cammi, R.; Pomelli, C.; Ochterski, J. W.; Ayala, P. Y.; Morokuma, K.; Voth, G. A.; Salvador, P.; Dannenberg, J. J.; Zakrzewski, V. G.; Dapprich, S.; Daniels, A. D.; Strain, M. C.; Farkas, O.; Malick, D. K.; Rabuck, A. D.; Raghavachari, K.; Foresman, J. B.; Ortiz, J. V.; Cui, Q.; Baboul, A. G.; Clifford, S.; Cioslowski, J.; Stefanov, B. B.; Liu, G.; Liashenko, A.; Piskorz, P.; Komaromi, I.; Martin, R. L.; Fox, D. J.; Keith, T.; A1-Laham, M. A.; Peng, C. Y.; Nanayakkara, A.; Challacombe, M.; Gill, P. M. W.; Johnson, B.; Chen, W.; Wong, M. W.; Gonzalez, C.; Pople, J. A. Gaussian 03, revision A.1; Gaussian, Inc.: Pittsburgh, PA, 2004.
34. Bader, R. F. W. Atoms in Molecules, A Quantum Theory; Clarendon Press: Oxford U.K., 1990.
35. Bader, R. F. W.; Beddall, P. M. J. Chem. Phys. 1972, 56, 3320.
36. Bader, R. F. W. AIMPAC, Suite of programs for the Theory of Atoms in Molecules; McMaster University: Hamilton, Ontario, Canada, 1991.
37. For details see: Krygowski, T. M.; Zachara, J. E.; Szatylowicz, H. J. Phys. Org. Chem. 2005, 18, 110-114.
38. (a) Hiberty, P. C.; Ohanessian, G. J. Am. Chem. Soc. 1984, 106, 6963-6968.
39. (b) Krygowski, T. M.; Maurin, J. J. Chem. Soc. Perkin Trans. 2 1989, 695-698.
40. Krygowski, T. M. J. Chem. Res. 1987, 120-121.
41. Szatylowicz, H.; Krygowski, T. M. J. Mol. Struct. 2007, 844/845, 200-207.