Prediction models for the Abraham hydrogen bond donor strength: Comparison of semi-empirical, ab initio, and DFT methods

Journal of Physical Organic Chemistry

Volumn 24, Issue 11, 2011, Pages 1072-1080

  Schwöbel, Johannes A H ^a,b   Ebert, Ralf Uwe ^a   Kühne, Ralph ^a   Schüürmann, Gerrit ^a,b  

^a HELMHOLTZ CENTRE FOR ENVIRONMENTAL RESEARCH UFZ   (Germany)

^b TU BERGAKADEMIE FREIBERG   (Germany)

Author keywords

Abraham parameter; AM1; B3LYP; H bond acidity; H bond donor strength; HF; hydrogen bonding; linear solvation energy relationship; local molecular reactivity; LSER; quantum chemical

Indexed keywords

ABRAHAM PARAMETER; AM1; B3LYP; DONOR STRENGTH; H-BOND ACIDITY; HYDROGEN BONDINGS; LINEAR SOLVATION ENERGY RELATIONSHIPS; LSER; MOLECULAR REACTIVITY; QUANTUM CHEMICAL;

AMIDES; CALCULATIONS; CHARGE TRANSFER; CHEMICAL ANALYSIS; DENSITY FUNCTIONAL THEORY; HYDROGEN; MATHEMATICAL MODELS; ORGANIC COMPOUNDS; QUANTUM CHEMISTRY;

HYDROGEN BONDS;

EID: 80053325185     PISSN: 08943230     EISSN: 10991395     Source Type: Journal    
DOI: 10.1002/poc.1834     Document Type: Article

References (40)

1. G. A. Jeffrey, An Introduction to Hydrogen Bonding, 1st edn, Oxford University Press, Oxford, UK, 1997.
2. S. Scheiner, Hydrogen Bonding: A Theoretical Perspective, 1st edn, Oxford University Press, Oxford, UK, 1997.
3. I. Rozas, Phys. Chem. Chem. Phys. 2007, 9, 2782.
4. F. Hibbert, J. Emsley, in Advances in physical organic chemistry, Vol. 26 (Ed.:, D. Bethell,), Academic Press Inc, London, United Kingdom, 1990, pp. 255.
5. K. R. Bowen, K. B. Flanagan, W. E. Acree, Jr., M. H. Abraham, C. Rafols, Sci. Total Environm. 2006, 371, 99.
6. M. H. Abraham, M. Rosés, J. Phys. Org. Chem. 1994, 7, 672.
7. M. H. Abraham, J. C. Dearden, G. M. Bresnen, J. Phys. Org. Chem. 2006, 19, 242.
8. M. H. Abraham, W. E. Acree, Jr, J. Phys. Org. Chem. 2008, 21, 823.
9. M. H. Abraham, J. A. Platts, J. Org. Chem. 2001, 66, 3484.
10. L. M. Sprunger, J. Gibbs, J. W. E. Acree, M. H. Abraham, QSAR Comb. Sci. 2009, 28, 72.
11. M. H. Abraham, Eur. J. Med. Chem. 2004, 39, 235.
12. J. S. Arey, W. H. Green, P. M. Gschwend, J. Phys. Chem. B 2005, 109, 7564.
13. M. H. Abraham, A. Ibrahim, A. M. Zissimos, J. Chromatogr. A 2004, 1037, 29.
14. P. Gilli, L. Pretto, V. Bertolasi, G. Gilli, Acc. Chem. Res. 2009, 42, 33.
15. J. A. Platts, D. Butina, M. H. Abraham, A. Hersey, J. Chem. Inform. Comput. Sci. 1999, 39, 835.
16. J. A. Platts, M. H. Abraham, D. Butina, A. Hersey, J. Chem. Inform. Comput. Sci. 2000, 40, 71.
17. G. Schüürmann, R.-U. Ebert, R. Kühne, Chimia 2006, 60, 691.
18. G. Schüürmann, R.-U. Ebert, M. Nendza, J. C. Dearden, A. Paschke, R. Kühne, in Risk Assessment of Chemicals. An Introduction, 2nd edn (Eds:, K. van Leeuwen, T. Vermeire,), Springer Science, Dordrecht, Netherlands, 2007, pp. 375.
19. ADME Boxes 4.1, Pharma Algorithms Inc., Toronto, ON, Canada, 2008 (now distributed as ACD/ADME Suite 5.0, ACD/Labs, Toronto, ON, Canada, 2010).
20. T. J. Sheldon, C. S. Adjiman, J. L. Cordiner, Fluid Phase Eq. 2005, 231, 27.
21. J. A. Platts, Phys. Chem. Chem. Phys. 2000, 2, 973.
22. M. Nocker, S. Handschuh, C. Tautermann, K. R. Liedl, J. Chem. Inf. Model. 2009, 49, 2067.
23. A. S. Ãzen, F. de Proft, V. Aviyente, P. Geerlings, J. Phys. Chem. A 2006, 110, 5860.
24. M. Devereux, P. L. A. Popelier, I. M. McLay, Phys. Chem. Chem. Phys. 2009, 11, 1595.
25. A. A. Oliferenko, P. V. Oliferenko, J. G. Huddleston, R. D. Rogers, V. A. Palyulin, N. S. Zefirov, A. R. Katritzky, J. Chem. Inf. Comput. Sci. 2004, 44, 1042.
26. P. V. Oliferenko, A. A. Oliferenko, G. Poda, V. A. Palyulin, N. S. Zefirov, A. R. Katritzky, J. Chem. Inf. Model. 2009, 49, 634.
27. T. Ghafourian, J. C. Dearden, J. Pharm. Pharmacol. 2000, 52, 603.
28. J. Jover, R. Bosque, J. Sales, J. Chem. Inf. Comput. Sci. 2004, 44, 1098.
29. J. Schwöbel, R.-U. Ebert, R. Kühne, G. Schüürmann, J. Comput. Chem. 2009, 30, 1454.
30. J. Schwöbel, R.-U. Ebert, R. Kühne, G. Schüürmann, J. Chem. Inf. Model. 2009, 49, 956.
31. J. Schwöbel, R.-U. Ebert, R. Kühne, G. Schüürmann, J. Phys. Chem. A 2009, 113, 10104.
32. A. Klamt, Chemosphere 1993, 32, 1273.
33. A. Klamt, Chemosphere 1995, 32, 717.
34. M. J. S. Dewar, E. G. Zoebisch, E. F. Healy, J. J. P. Stewart, J. Am. Chem. Soc. 1985, 107, 3902.
35. J. J. P. Stewart, Fujitsu Limited, Tokyo, Japan, 1999.
36. M. J. Frisch, G. W. Trucks, H. B. Schlegel, G. E. Scuseria, M. A. Robb, J. R. Cheeseman, J. A. Montgomery, 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. Pompelli, 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. Raghavavachari, 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 C.02, Gaussian Inc., Pittsburgh PA, 2003.
37. J. J. Moré, T. K. Garbow, K. E. Hillstrom, Argonne National Laboratory Report ANL-80-74, Argonne, IL, 1980.
38. G. Schüürmann, R.-U. Ebert, J. Chen, B. Wang, R. Kühne, J. Chem. Inf. Model. 2008, 48, 2140.
39. M. H. Abraham, D. S. Ballantine, B. K. Callihan, J. Chromatogr. A 2000, 878, 115.
40. G. Schüürmann, in Predicting Chemical Toxicity and Fate (Eds:, M. T. D. Cronin, D. J. Livingstone,), CRC Press, Boca Raton, FL, USA, 2000, pp. 85.