Synthesis and spectroscopic study of a new lanthanum(III) complex of 3,3′-benzylidenedi-4-hydroxycoumarin

Synthesis and Reactivity in Inorganic and Metal-Organic Chemistry

Volumn 34, Issue 9, 2004, Pages 1635-1650

  Trendafilova, N ^a   Kostova, I ^b   Manolov, I ^b   Bauer, G ^c   Mihaylov, T ^a   Georgieva, I ^a  

^a INSTITUTE OF GENERAL AND INORGANIC CHEMISTRY   (Bulgaria)

^b MEDICAL UNIVERSITY OF SOFIA   (Bulgaria)

^c VIENNA UNIVERSITY OF TECHNOLOGY   (Austria)

Author keywords

3,3 Benzylidenedi 4 hydroxycoumarin; IR and NMR spectra; La(III)

Indexed keywords

3,3' BENZYLIDENEBIS(4 HYDROXYCOUMARIN); COUMARIN DERIVATIVE; HYDROXYL GROUP; LANTHANUM; METAL ION; OXYGEN; UNCLASSIFIED DRUG;

ARTICLE; ATOM; CARBON NUCLEAR MAGNETIC RESONANCE; CHEMICAL MODIFICATION; COMPLEX FORMATION; INFRARED SPECTROSCOPY; MASS SPECTROMETRY; PREDICTION; PROTON NUCLEAR MAGNETIC RESONANCE; PROTON TRANSPORT; STATISTICAL SIGNIFICANCE; VIBRATION;

EID: 9744224510     PISSN: 00945714     EISSN: None     Source Type: Journal    
DOI: 10.1081/SIM-200026618     Document Type: Article

References (29)

1. Issa, Y.M.; Abdel-Latis, S.A. Spectrometric, thermal and conductometric studies of some lanthanide, thorium and uranyl complexes with some hydroxynitrosocoumarins. J. Thermal Anal. Calorim. 1998, 51 (2), 449-465.
2. Issa, Y.M.; Omar, M.M.; Sabrah, B.A.; Mohamed, S.K. Complexes of cerium(III), thorium(IV) and dioxouranium(II) with 8-(arylazo)-7-hydroxy-4- methylcoumarin dyes. J. Indian Chem. Soc. 1992, 69 (4), 186-189.
3. Bisi, C.C.; Carugo, O. Studies on fluorescent lanthanide complexes. New complexes of lanthanides(III) with coumarinic-3-carboxylic acid. Inorg. Chim. Acta 1989, 159 (2), 157-161.
4. Jiang, D.D.; Deng, R.; Wu, J. Synthesis and properties of lanthanide compounds of 3-sulfo-4-hydroxycoumarin. Wuji Huaxue. 1989, 5 (1), 21-28 (Chem. Abstr. 1990, 112 (2), 15547).
5. Jiang, D.D.; Deng, R.; Wu, J. Synthesis and properties of lanthanide compounds of 3-sulfo-4-hydroxycoumarin. Wuji Huaxue. 1989, 5 (1), 21-28 (Chem. Abstr. 1990, 112 (2), 15547).
6. Deng, R.; Wu, J.; Long, L. Lanthanide complexes of bis(4-hydroxy-3- coumarinyl) acetic acid and their anticoagulant action. Bull. Soc. Chim. Belg. 1992, 101 (6), 439-443.
7. Jiang, D.D.; Zhu, G.; Deng, R.; Wu, J. Synthesis and properties of lanthanide compounds of 3-acetoacetyl-4-hydroxycoumarin. Wuji Huaxue. 1995, 11 (1), 15-18 (Chem. Abstr. 1995, 722 (24), 305173).
8. Jiang, D.D.; Zhu, G.; Deng, R.; Wu, J. Synthesis and properties of lanthanide compounds of 3-acetoacetyl-4-hydroxycoumarin. Wuji Huaxue. 1995, 11 (1), 15-18 (Chem. Abstr. 1995, 722 (24), 305173).
9. Kostova, I.; Manolov, I.; Nicolova, I.; Konstantinov, S.; Karaivanova, M. New lanthanide complexes of 4-methyl-7-hydroxycoumarin and their pharmacological activity. Eur. J. Med. Chem. 2001, 36, 339-347.
10. Manolov, I.; Kostova, I.; Netzeva, T.; Kostantinov, S.; Karaivanova, M. Cytotoxic activity of cerium complexes with coumarin derivatives. Molecular modeling of the ligands. Arch. Pharm. Pharm. Med. Chem. 2000, 333 (4), 93-98.
11. Kostova, I.; Manolov, I.; Konstantinov, S.; Karaivanova, M. Synthesis, physicochemical characterization and cytotoxic screening of new complexes of Ce, La and Nd with warfarin and coumachlor sodium salts. Eur. J. Med. Chem. 1999, 34 (1), 63-68.
12. Manolov, I.; Kostova, I.; Konstantinov, S.; Karaivanova, M. Synthesis, physicochemical characterization and cytotoxic screening of new complexes of Ce, La and Nd with niffcoumar sodium salt. Eur. J. Med. Chem. 1999, 34 (11), 853-858.
13. Zhao, H.; Neamati, N.; Hong, H.; Mazumder, A.; Wang, S.; Sunder, S.; Milne, G.W.A.; Pommier, Y.; Burke, T.R., Jr. Coumarin-based inhibitors of HIV integrase. J. Med. Chem. 1997, 40, 242-249.
14. Valente, E.J.; Eggleston, D.S. Structure of (phenyl)bis(4-hydroxybenzo- 2H-pyran-2-one-3-yl)methane. Acta Cryst. 1989, C45, 785-787.
15. Hutchinson, D.W.; Tomlinson, J.A. The structure of dicoumarol and related compounds. Tetrahedron 1969, 25, 2531-2537.
16. Schiøtt, B.; Iversen, B.B.; Madsen, G.K.H.; Bruice, T.C. Characterization of the short strong hydrogen bond in benzoylacetone by ab initio calculations and accurate diffraction experiments. Implications for the electronic nature of low-barrier hydrogen bonds and enzymatic reactions. J. Am. Chem. Soc. 1998, 120, 12117-12124.
17. Garcia-Viloca, M.; Gonzalez-Lafont, A.; Lluch, J.M. Theoretical study of the low-barrier hydrogen bond in the hydrogen maleate anion in the gas phase. Comparison with normal hydrogen bonds. J. Am. Chem. Soc. 1997, 119, 1081-1086.
18. Gilli, P.; Bertolasi, V.; Ferretti, V.; Gilli, G. Covalent nature of the strong homonuclear hydrogen bond. Study of the O-H⋯O System by crystal structure correlation methods. J. Am. Chem. Soc. 1994, 116, 909-915.
19. Gilli, G.; Bellucci, F.; Ferretti, V.; Bertolasi, V. Evidence for resonance-assisted hydrogen bonding from crystal structure correlations on the enol form of the β-diketone fragment. J. Am. Chem. Soc. 1989, 111, 1023-1028.
20. 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; A.7 Gaussian, Inc.: Pittsburgh, PA, 1998.
21. Becke, A.D. Density-functional thermochemistry. III. The role of the exact exchange. J. Chem. Phys. 1993, 98 (7), 5648-5652.
22. Lee, C.; Yang, W.; Parr, R.G. Development of the Colle-Salvetti correlation-energy formula into a functional of the electron density. Phys. Rev. 1998, B37, 785.
23. Arulmozhiraja, S.; Kolandaivel, P. Condesed Fukui function: dependence on atomic charges. Mol. Phys. 1997, 90 (1), 55-62.
24. Yang, W.; Mortier, W.J. The use of global and local molecular parameters for the analysis of the gas-phase basicity of amines. J. Am. Chem. Soc. 1986, 108, 5708-5711.
25. NIST Mass Spec Data Center, S.E. Stein, Director, Infrared Spectra in NIST Chemistry WebBook; Linstrom, P.J., Mallard, W.G., Eds. NIST Standard Reference Database Number 69; National Institute of Standards and Technology Gaithersburg: MD, 2003 (http://webbook.nist.gov).
26. NIST Mass Spec Data Center, S.E. Stein, Director, Infrared Spectra in NIST Chemistry WebBook; Linstrom, P.J., Mallard, W.G., Eds. NIST Standard Reference Database Number 69; National Institute of Standards and Technology Gaithersburg: MD, 2003 (http://webbook.nist.gov).
27. Lewis, F.D.; Barancyk, S.V. Lewis acid catalysis of photochemical reactions. 8. Photodimerization and cross-cycloaddition of coumarin. J. Am. Chem. Soc. 1989, 111, 8653-8661.
28. Cotton, F.A.; Wilkinson, G.F.R.S. Advanced Inorganic Chemistry, 3rd Ed.; Interscience Publischers, John Willey & Sons, Inc.: New York, Sydney, Toronto, 1972.
29. Mitra, A.K.; De, A.; Karchaudhuri, N.; Misra, S.K.; Mukhopadhyay, A.K. Carbon-13 NMR chemical shifts of some dicoumarols and benzopyranodicoumarins. J. Indian Chem. Soc. 1998, 75, 526-528.