Theoretical study of the substituent effect on the intramolecular hydrogen bonds in di(4-hydroxycoumarin) derivatives

International Journal of Quantum Chemistry

Volumn 106, Issue 6, 2006, Pages 1304-1315

  Mihaylov, Tzvetan ^a   Georgieva, Ivelina ^a   Bauer, Günther ^b   Kostova, Irena ^c   Manolov, Ilia ^c   Trendafilova, Natasha ^a  

^a INSTITUTE OF GENERAL AND INORGANIC CHEMISTRY   (Bulgaria)

^b VIENNA UNIVERSITY OF TECHNOLOGY   (Austria)

^c MEDICAL UNIVERSITY OF SOFIA   (Bulgaria)

Author keywords

3,3 (pyridinomethylene)di(4 hydroxycoumarin); Intramolecular hydrogen bondings; MO and DFT study; Molecular electrostatic potential

Indexed keywords

DERIVATIVES; ELECTROSTATICS; OPTIMIZATION; PROBABILITY DENSITY FUNCTION; ROTATION;

3,3′-(PYRIDINOMETHYLENE)DI(4-HYDROXYCOUMARIN); INTRAMOLECULAR HYDROGEN BONDINGS; MO AND DFT STUDY; MOLECULAR ELECTROSTATIC POTENTIAL;

HYDROGEN BONDS;

EID: 33645682072     PISSN: 00207608     EISSN: 1097461X     Source Type: Journal    
DOI: 10.1002/qua.20886     Document Type: Conference Paper

References (37)

1. Rosskopt, F.; Kraus, J.; Franz G. Pharmazie 1992, 47, 139.
2. Zhao, H.; Neamati, N.; Hong, H.; Mazumder, A.; Wang, S.; Sunder, S.; Milne, G. W. A; Pommier, Y.; Burke, T. R., Jr. J Med Chem 1997, 40, 242.
3. Lu, A.; Liu B.; Liu, H.; Zhou, J.; Xie, G. Internet Electronic Conference of Molecular Design; November 23-December 6, 2003.
4. Hutchinson, D. W.; Tomlinson, J. A. Tetrahedron 1969, 25, 2531.
5. Schiott, B.; Iversen, B. B.; Madsen, G. K. H.; Bruice, T. C. J Am Chem Soc 1998, 120, 12117 (and references therein).
6. Viloca, M. G.; Lafont, A. G.; Lluch, J. M. J Am Chem Soc 1997, 119, 1081.
7. Tomlinson, J. A. Ph. D. thesis; University of Warwick, 1968.
8. Bravic, G.; Gaultier, J.; Hauw, C. CR Acad Sci Ser C1968, 267, 1790.
9. Valente, E. J.; Eggleston, D. S. Acta Crystallogr C 45 1989, 785.
10. Trendafilova, N.; Bauer, G.; Mihaylov, T. Chem Phys 2004, 302, 95.
11. Kostova, I.; Manolov, I.; Momekov, G. Eur J Med Chem 2004, 39, 765.
12. Buemi, G. J Mol Struct (Theochem) 2000, 499, 21.
13. Buemi, G.; Zuccarello, F. J Mol Struct (Theochem) 2002, 581, 71.
14. Frisch, M. J.; Trucks, G. W.; Schlegel, H. B.; Scuseria, G. E.; Robb, M. A.; Cheeseman, J. R.; Zakrzewski, V. G.; Montgomery, J. A., Jr.; Stratmann, R. E.; Burant, J. C.; Dapprich, S.; Millam, J. M.; Daniels, A. D.; Kudin, K. N.; Strain, M. C.; Farkas, O.; Tomasi, J.; Barone, V.; Cossi, M.; Cammi, R.; Mennucci, B.; Pomelli, C.; Adamo, C.; Clifford, S.; Ochterski, J.; Petersson, G. A.; Ayala, P. Y.; Cui, Q.; Morokuma, K.; Malick, D. K.; Rabuck, A. D.; Raghavachari, K.; Foresman, J. B.; Cioslowski, J.; Ortiz, J. V.; Stefanov, B. B.; Liu, G.; Liashenko, A.; Piskorz, P.; Komaromi, I.; Gomperts, R.; Martin, R. L.; Fox, D. J.; Keith, T.; Al-Laham, M. A.; Peng, C. Y.; Nanayakkara, A.; Gonzalez, C.; Challacombe, M.; Gill, P. M. W.; Johnson, B.; Chen, W.; Wong, M. W.; Andres, J. L.; Gonzalez, C.; Head-Gordon, M.; Replogle, E. S.; Pople, J. A. Gaussian 98; Gaussian: Pittsburgh, PA, 1998.
15. Becke, A. D. J Chem Phys 1993, 98, 5648.
16. Lee, C.; Yang, W.; Parr, R. G. Phys Rev B 37 1998, 785.
17. Rablen, P. R.; Lockman, J. W.; Jorgensen, W. L. J Phys Chem A 1998, 102, 3782.
18. Novoa, J. J.; Sosa, C. J. J Phys Chem 1995, 99, 15837.
19. Hamann, D. R. Phys Rev B 1997, 55, R10157.
20. Maerker, C.; Schleyer, P. v. R.; Liedl, K. R.; Ma, T.-K.; Quack, M.; Suhn, M. A. J Comp Chem 1997, 18, 1695.
21. Lonzynski, M.; Rusinska-Raszak, D.; Mack, H.-G. J Phys Chem A 1998, 102, 2899.
22. Raghavachari, K.; Trucks, G. W.; Pople, J. A.; Head-Gordon, M. Chem Phys Lett 1989, 157, 479.
23. Buemi, G. Chem Phys 2002, 277, 241.
24. (a) Reed, A. E.; Weinstock, R. B.; Weinhold, F. J Chem Phys 1985, 83, 735;
25. (b) Reed, A. E.; Curtiss, L. A.; Weinhold, F. Chem Rev 1988, 88, 899;
26. (c) Weinhold, F.; Carpenter, J. E. The Structure of Small Molecules and Ions; Plenum: New York, 1988.
27. Mulliken, R. S. J Chem Phys 1955, 23, 1833.
28. Munoz-Caro, C.; Nino, A.; Senent, M. L.; Leal, J. M.; Ibeas, S. J Org Chem 2000, 65, 405.
29. Miertus, S.; Scrocco, E.; Tomasi, J. Theor Chem Acc 2000, 103, 343.
30. Okulik, N.; Jubert, A. H. Internet Elect J Mol Design 2003, 2, 1.
31. Soliva, R.; Luque F. J.; Orozeo, M. Theor Chem Acc 1997, 98, 42.
32. Politzer, P.; Murray, J. Theor Chem Acc 2002, 108, 134.
33. Buemi, G.; Zuccarello, F.; Venuvanalingam, P.; Ramalingam, M.; Ammal, S. S. C. J Chem Soc Faraday Trans 1998, 94, 3313.
34. Buemi, G.; Zuccarello, F. Chem Phys 2004, 306, 115.
35. Stein, S. E. NIST Mass Spec Data Center; Infrared Spectra in NIST Chemistry; WebBook; NIST Standard Reference Database No. 69; in Coblentz No. 05110, 1961/06/13.
36. Politzer, P.; Murray, J. S. Theoretical Biochemistry and Molecular Biophysics: A Comprehensive Survey; Vol 2: Protein; Beveridge, D. L.; Lavery, R., Eds.; Electrostatic Potential Analysis of dibenzo-p-dioxins and Structurally Similar Systems in Relation to their Biological Activities; Adenine: Schenectady, NY, 1991.
37. Kostova, I.; Trendafilova, N.; Momekov, G. J Inorg Biochem 2005, 99, 477.