Isomerization of 4′-methoxy-flavanone in alkaline medium. Determination of the enolate formation constant

Journal of Molecular Structure: THEOCHEM

Volumn 636, Issue 1-3, 2003, Pages 157-166

  Andujar S A ^a   Filippa, M A ^a   Ferretti, F H ^a   Blanco, S E ^a  

^a UNIVERSIDAD NACIONAL DE SAN LUIS   (Argentina)

Author keywords

4 methoxy flavanone; Ab initio calculations; Enolate formation constant; Isomerization mechanism; Solvent effects

Indexed keywords

2' HYDROXY 4 METHOXYCHALCONE; 4' METHOXYFLAVANONE; ALCOHOL; FLAVANONE DERIVATIVE; POTASSIUM CHLORIDE; SOLVENT; UNCLASSIFIED DRUG; WATER;

AB INITIO CALCULATION; ACID BASE BALANCE; ALKALINITY; ARTICLE; CHEMICAL REACTION KINETICS; DRUG STRUCTURE; DRUG SYNTHESIS; IONIC STRENGTH; ISOMERISM; PH; REACTION ANALYSIS; SPECTROPHOTOMETER; STEREOCHEMISTRY;

EID: 0142074293     PISSN: 01661280     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0166-1280(03)00474-3     Document Type: Article

References (34)

1. J.B. Harborne, The Flavonoids, Advances in Research Since 1986, Chapman & Hall, New York, 1999.
2. B. Modak, A. Arrieta, R. Torres, A. Urzua, Bol. Soc. Chil. Quim. 47 (2002) 19.
3. L.E. Alcaráz, S.E. Blanco, O.N. Puig, F. Tomás, F.H. Ferretti, J. Theor. Biol. 205 (2000) 231-240.
4. P. Tuchinda, W. Pompimon, V. Reutrakul, M. Pohmakotr, C. Yoosook, N. Kongyai, S. Sophasan, K. Sujarit, S.E. Upathum, T. Santisuk, Tetrahedron 58 (2002) 8073-8086.
5. A. Salvi, C. Bruhlmann, E. Migliavacca, P.A. Carrupt, K. Hostettmann, B. Testa, Helv. Chim. Acta 85 (2002) 867-881.
6. A.M. Ponce, S.E. Blanco, A.S. Molina, R. García-Domenech, J. Gálvez-Alvarez, J. Chem. Inf. Comput. Sci. 40 (2000) 1039-1045.
7. M.H. Siess, M. Guillermic, A.M. LeBon, M. Suschetet, Xenobiotica 19 (1989) 1379-1386.
8. L. Magnani, E. Gaydou, J.C. Hubaud, Anal. Chim. Acta 411 (2000) 209-216.
9. C.A. Rice-Evans, L. Packer, Flavonoids in Health and Disease, Marcel Dekker, New York, 1998.
10. M. Gibaldi, Biopharmaceutics and Clinical Pharmacokinetics, fourth ed., Lep and Febiger, USA, 1991, pp. 40-60.
11. J.I. Wells, Pharmaceutical Preformulation: the Physicochemical Properties of Drug Substances, Ellis Horwood, England, 1990, pp. 15, 80.
12. J.T. Cartensen, C.T. Rhodes, Drug Stability, third ed., Marcel Dekker, New York, 1999, pp. 145-189 and 209-260.
13. J.M. Luco, L.J. Yamín, F.H. Ferretti, J. Pharm. Sci. 84 (1995) 903-908.
14. E.I. Gasull, S.E. Blanco, F.H. Ferretti, Annu. Assoc. Quím. Argent. 87 (1999) 73-82.
15. A. Albert, E.P. Serjeant, The Determination of ionization Constants, third ed., Chapman and Hall, New York, 1984.
16. S.E. Blanco, N.B. Debattista, J.M. Luco, F.H. Ferretti, Tetrahedron Lett. 34 (1993) 4615-4618.
17. L. Reichel, K. Müller, Ber. 74B (1941) 1741-1742.
18. H. Wagner, L. Farkas, Synthesis of flavonoids, in: J.B. Harborne, T.J. Mabry, H. Mabry (Eds.), The Flavonoids, Part I, Academic Press, New York, 1975, p. 131.
19. J.G. Grasselli, M.S. William, M. Ritcher (Eds.), Atlas of Spectral Data and Physical Constants for Organic Compounds, vol. III, CRS Press, New York, 1975, pp. 39-45.
20. B. Fried, J. Sherma, Thin-Layer Chromatography (Chromatographic Science), fourth ed., vol. 81, Marcel Dekker, USA, 1999, p. USA.
21. K.S. Lau, A. Mantas, G.A. Chass, F.H. Ferretti, M.R. Estrada, G. Zamarbide, I.G. Csizmadia, Can. J. Chem. 80 (2002) 845-855.
22. Program CS Chem3D 5.0, Molecular Modeling and Analysis, CambridgeSoft Corporation, MA, USA, 2000.
23. 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. 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. Ortiz, A.G. Baboul, B.B. Stefanov, G. Liu, A. Liashenko, P. Piskorz, I. 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 98, Revision A.9, Gaussian, Inc., Pittsburgh PA, 1998.
24. S. Miertus, E. Scrocco, J. Tomasi, Chem. Phys. 65 (1982) 239.
25. C.Y. Peng, P.Y. Ayala, H.B. Schlegel, J. Comp. Chem. 17 (1996) 46.
26. J.J.P. Furlong, N.S. Nudelman, J. Chem. Soc. Perkin Trans. 2 (7) (1988) 1213-1217.
27. N.S. Nudelman, J.J.P. Furlong, J. Phys. Org. Chem. 4 (1991) 263-267.
28. V.L. Arcus, C.D. Simpson, L. Main, J. Chem. Res. (S) (1992) 80-81.
29. S.E. Blanco, J.J. Silber, G.E. Narda, L.J. Yamín, F.H. Ferretti, J. Colloid Interface Sci. 180 (1996) 144-148.
30. N.S. Isaacs, Physical Organic Chemistry, second ed., Longman, England, 1996, pp. 392-397.
31. A. Stretwiser, C.H. Heathcokc, E.M. Kosower, Introduction to Organic Chemistry, fourth ed., 1992, p. 421.
32. V.D. Orlov, I.A. Borovoi, V.N. Tishchenco, V.F. Lavrushin, Zh. Obshchei Khimii 46 (1976) 2746-2747.
33. T. Fahmy, Xlstat 5.0 Program, Paris, 2001.
34. I.G. Csizmadia, Basic Principles for Introductory Organic Chemistry, Quirk Press, Toronto, 1997, p. 158.