Correlation of aqueous pKa values of carbon acids with theoretical descriptors: A DFT study

Journal of Molecular Structure: THEOCHEM

Volumn 818, Issue 1-3, 2007, Pages 1-6

  Charif, I E ^a   Mekelleche, S M ^a   Villemin, D ^b   Mora Diez, N ^c  

^a UNIVERSITY OF TLEMCEN   (Algeria)

^b UNIVERSITÉ DE CAEN   (France)

^c THOMPSON RIVERS UNIVERSITY   (Canada)

Author keywords

Aqueous pKa; Carbon acidity; Deprotonation energy; DFT calculations; NBO analysis

Indexed keywords

EID: 84962427357     PISSN: 01661280     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.theochem.2007.04.037     Document Type: Article

References (38)

1. Smith M.B., and March J. March's Advanced Organic Chemistry. Sixth ed. (2007), John Wiley, New York pp. 359-364
2. Dewar M.J.S., and Dieter K.M. J. Am. Chem. Soc. 108 (1986) 8075
3. Siggel M.R., Thomas T.D., and Saethre L.J. J. Am. Chem. Soc. 110 (1988) 91
4. Kass S.R. J. Comp. Chem. 11 (1990) 94
5. Burk P., and Koppel I.A. Theor. Chim. Acta. 86 (1993) 417
6. Burk P., Herodes K., Koppel I., and Koppel I.A. Int. J. Quantum. Chem. 27 (1993) 633
7. Koppel I.A., Taft R.W., Anvia F., Zhu S.Z., Hu L.Q., Sun K.S., DesMarteau D.D., Yagupolskii L.M., Yagupolskii Yu.L., Ignat'ev N.V., Kondratenko N.V., Volkonskii A.Yu., Vlassov V.M., Notario R., and Maria P.C. J. Am. Chem. Soc. 116 (1994) 3047
8. Burk P., Koppel I.A., Koppel I., Yagupolskii L.M., and Taft R.W. J. Comp. Chem. 17 (1996) 30
9. Smith B.J., and Radom L. J. Phys. Chem. 99 (1995) 6468
10. Smith B.J., and Radom L. J. Phys. Chem. Lett. 245 (1995) 123
11. Catalan J., and Palomar J. Chem. Phys. Lett. 293 (1998) 511
12. Choho K., Van Lier G., Van de Woude G., and Geerlings P. J. Chem. Soc. Perkin 2 (1996) 1723
13. Yang W., and Mortier W.J. J. Am. Chem. Soc. 108 (1986) 5708
14. Contreras R., Fuentealba P., Galvan M., and Perez P. Chem. Phys. Lett. 304 (1999) 405
15. Pérez P., Simon-Manso Y., Aizman A., Fuentealba P., and Contreras R. J. Am. Chem. Soc. 122 (2000) 4756
16. D'Souza F., Zandler M.E., Deviprasad G.R., and Kutner W. J. Phys. Chem. A 104 (2000) 6887
17. Rezende M.C. J. Br. Chem. Soc. 12 (2001) 73
18. Alkorta I., and Elguero J. Tetrahedron 53 (1997) 9741
19. Rezende M.C. Tetrahedron 57 (2001) 5923
20. Serjeant E.P., and Dempsey B. Ionization Constants of Organic Acids in Aqueous Solution. IUPAC Chemical Data Series (1979), Pergamon Press, New York
21. Pearson R.G., and Dillon R.L. J. Am. Chem. Soc. 75 (1953) 2439
22. Bordwell F.G. Acc. Chem. Res. 21 (1988) 456-463
23. Reed A.E., Curtiss L.A., and Weinhold F. Chem. Rev. 88 (1988) 899
24. Reed A.E., Weinstock R.B., and Weinhold F. J. Chem. Phys. 83 (1985) 735
25. Brunck T.K., and Weinhold F. J. Am. Chem. Soc. 101 (1979) 1700
26. Reed A.E., and Weinhold F. J. Chem. Phys. 83 (1985) 1736
27. Reed A.E., and Weinhold F. J. Chem. Phys. 78 (1983) 4066
28. Reed A.E., and Weinhold F. Isr. J. Chem. 31 (1991) 277
29. M.J. Frisch, G.W. Trucks, H.B, Schlegel, G.E. Scuseria, M.A.Robb, J.R. Cheeseman, V.G. Zakrzewski, J.A. Montgomery, Jr, R.E. Stratmann, J.C. Burant, S.B Dapprich, J.M. Millam, A.D. Daniels, K.N. Kudin, M.C. Strain, O. Farkas, J. Tomasi, V. Barone, M. Cossi, R. Cammi, B. Mennucci, C. Pomelli, C. Adamo, S. Clifford, J. Ochterski, G.A. Petersson, P.Y. Ayala, Q. Cui, K. Morokuma, D.K. Malick, A.D. Rabuck, K. Raghavachari, J.B. Foresman, J. Cioslowski, J.V. Oritz, A.G. Baboul, B.B. Stefanv, G. Liu, A. Liashenko, P. Piskorz, L. Komaromi, R. Gomperts, 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, J.L. Andres, C. Gonzalez, M. Head-Gordon, E.S. Replogle, J.A. Pople, GAUSSIAN 98W, Revision A.9, Gaussian, Inc., Pittsburgh, PA, 1998.
30. Liptak M.D., Grass K.C., Seybold P.G., Feldgus S., and Shields G.C. J. Am. Chem. Soc. 124 (2002) 6421
31. Miertus S., Scrocco E., and Tomasi J. J. Chem. Phys. 55 (1981) 117
32. Miertus S., and Tomasi J. J. Chem. Phys. 65 (1982) 239
33. Cossi M., Barone V., Cammi R., and Tomasi J. J. Chem. Phys. Lett. 255 (1996) 327
34. Brown T.N., and Mora-Diez N. J. Phys. Chem. B 110 (2006) 9270
35. Bordwell F.G., Bares J.E., Bartness J.E., McCollum G.J., Puy M.V.D., Vanier N.R., and Matthews W.S. J. Org. Chem. 42 (1977) 321
36. Bordwell F.G., and McCollum G.J. J. Org. Chem. 41 (1976) 2391
37. Hiberty P.C., and Byrman C.P. J. Am. Chem. Soc. 117 (1995) 9875
38. Wiberg K.B., Ochterski J., and Streitwieser A. J. Am. Chem. Soc. 118 (1996) 8291