Studies on equilibrium of anthranilic acid in aqueous solutions and in two-phase systems: Aromatic solvent-water

Biophysical Chemistry

Volumn 140, Issue 1-3, 2009, Pages 91-98

  Zapała, Lidia ^a   Kalembkiewicz, Jan ^a   Sitarz Palczak, Elzbieta ^a  

^a RZESZOW UNIVERSITY OF TECHNOLOGY   (Poland)

Author keywords

Anthranilic acid; Distribution constant; Microconstant; Tautomeric constant; Two phase equilibria

Indexed keywords

ANTHRANILIC ACID; AROMATIC COMPOUND; BENZENE; BROMOBENZENE; CHLOROBENZENE; ETHYLBENZENE; ORGANIC SOLVENT; TOLUENE; WATER;

ACID BASE BALANCE; AQUEOUS SOLUTION; ARTICLE; CHEMICAL ANALYSIS; CHEMICAL STRUCTURE; CONTROLLED STUDY; DIMERIZATION; DISSOCIATION CONSTANT; EQUILIBRIUM CONSTANT; ISOELECTRIC POINT; PH MEASUREMENT; POTENTIOMETRIC TITRATION; PRIORITY JOURNAL; SPECTROPHOTOMETRY;

ACID-BASE EQUILIBRIUM; ANTHRANILIC ACIDS; HYDROGEN-ION CONCENTRATION; POTENTIOMETRY; SOLVENTS; SPECTROPHOTOMETRY; WATER;

EID: 58549086378     PISSN: 03014622     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.bpc.2008.11.012     Document Type: Article

References (41)

1. Gichner T., Voutsinas G., Patrineli A., Kappas A., and Plewa M. Antimutagenicity of three isomers of aminobenzoic acid in Salmonella typhimurium. Mutat. Res. 309 (1994) 201-210
2. Fujii K. Evaluation of the newborn mouse model for chemical tumorigenesis. Carcinogenesis 12 (1991) 1409-1415
3. Jagadeesh R.V., Puttaswamy, Nirmala Vaz, and Made Gowda N.M. Ruthenium catalyzed oxidative conversion of isatins to anthranilic acids: mechanistic study. AIChE J. 54 (2008) 756-765
4. Kumar A., Bansal D., Bajaj K., Sharma S., and Srivastava V.K. Synthesis of some never derivatives of 2-amino benzoic acid as potent anti-inflammatory and analgesic agents. Bioorg. Med. Chem. 11 (2003) 5281-5291
5. Sorenson J.R.J. Copper chelates as possible active forms of the antiarthritic agents. J. Med. Chem. 19 (1976) 135-148
6. W. Szymański, J. Gmaj, C. Przybylski, L. Ruczyński, B. Głuchowski, B. Baniewicz, T. Guzewska, PL patent nr 163 029 (1994), CA: 123,115321f (1995).
7. Mannito P. Biosynthesis of Natural Products (1981), Ellis Horwood, Chichester
8. Jensen J.B., Egsgaard H., Vanonckelen H., and Jochimsen B.U. Catabolism of indole-3-acetic acid and 4-chloroindole-3-acetic and 5-chloroindole-3-acetic acid in Bradyrhizobium japonicum. J. Bacteriol. 177 (1995) 5762-5766
9. Creighton T.E., and Yanofsky C. Methods in Enzymology (1970), Academic Press, New York
10. Patten C.L., and Glick B.R. Bacterial biosynthesis of indole-3-acetic acid. Can. J. Microbiol. 42 (1996) 207-220
11. Costacurta A., and Vanderleyden J. Synthesis of phytohormones by plant-associated bacteria. Crit. Rev. Microbiol. 21 (1995) 1-18
12. Hansch C., Leo A., and Hoekman D. Exploring QSAR, Hydrophobic, Electronic and Steric Constant (1995), American Chemical Society, Washington
13. Hasegawa Y., Morita Y., Hase M., and Naguta M. Complexation of lanthanoid(III) with substituted benzoic or phenylacetic acids and extraction of these acids. Bull. Chem. Soc. Jpn. 62 (1989) 1486-1491
14. Noszal B. Group constant: a measure of submolecular basicity. J. Phys. Chem. 90 (1986) 4104-4110
15. Noszal B. Microspeciation of polypeptides. J. Phys. Chem. 90 (1986) 6345-6349
16. Sun J., Sakai S., Tauchi Y., Deguchi Y., Cheng G., Chen J., and Morimoto K. Protonation equilibrium and lipophilicity of olamufloxacin (HSR-903), a newly synthesized fluoroquinolone antibacterial. Eur. J. Pharm. Biopharm. 56 (2003) 223-229
17. Peinhardt G., and Wiese M. Microionization constant: novel approach for the determination of the zwitterionic equilibrium of hydroxyphenylalkylamines by photometric titration. Int. J. Pharm. 215 (2001) 83-89
18. Albert A., and Serjeant E.P. The Determination of Ionization Constants (1984), Chapman & Hall, New York
19. 6 group and related 3-hydroxypyridine derivatives. J. Am. Chem. Soc. 77 (1955) 2431-2437
20. Takács-Novák K., Avdeef A., Box K.J., Podányi B., and Szász G. Determination of protonation macro- and microconstants and octanol/water partition coefficient of the anti-inflammatory drug niflumic acid. J. Pharm. Biomed. Anal. 12 (1994) 1369-1377
21. Pagliara A., Carrupt P.-A., Caron G., Gaillard P., and Testa B. Lipophilicity profiles of ampholytes. Chem. Rev. 97 (1997) 3385-3400
22. Minczewski J., and Marczenko Z. Analytical Chemistry (1987), PWN, Warsaw (in Polish)
23. Langlois M.-H., Montagut M., Dubost J.-P., Grellet J., and Saux M.-C. Protonation equilibrium and lipophilicity of moxifloxacin. J. Pharm. Biomed. Anal. 37 (2005) 389-393
24. Handbook of Physicochemical Data (1974), WNT, Warsaw (in Polish)
25. Inczedy J. Complexation Equilibria in Analytical Chemistry (1979), PWN, Warsaw (in Polish)
26. Gluck S.J., Benkö M.H., Hallberg R.K., and Stelle K.P. Indirect determination of octanol-water partition coefficients by microemulsion electrokinetic chromatography. J. Chromatogr. A 744 (1996) 141-146
27. Miche H., Brumas V., and Berthon G. Copper(II) interactions with nonsteroidal anti-inflammatory agents. II. Anthranilic acid as a potential OH-inactivating ligand. J. Inorg. Biochem. 68 (1997) 27-38
28. Filella M., and May P.M. Reflections on the calculation and publication of potentiometrically-determined formation constant. Talanta 65 (2005) 1221-1225
29. Barbosa J., Barrón D., Beltrán J.L., Sanz-Nebot V., and PKPOT. a program for the potentiometric study of the ionic equilibria in aqueous and non-aqueous media. Anal. Chim. Acta 317 (1995) 75-81
30. Meloun M., and Pluhařovǎ M. Thermodynamic dissociation constants of codeine, ethylmorphine and homatropine by regression analysis of potentiometric titration data. Anal. Chim. Acta 416 (2000) 55-68
31. Meloun M., and Černohorskỳ P. Thermodynamic dissociation constants of isocaine, physostigmine and pilocarpine by regression analysis of potentiometic data. Talanta 52 (2000) 931-945
32. Takács-Novák K., and Tam K.Y. Multiwavelength spectrophotometric determination of acid dissociation constants. Part V: microconstants and tautomeric ratios of diprotic amphoteric drugs. J. Pharm. Biomed. Anal. 21 (2000) 1171-1182
33. Takács-Novák K., Józan M., and Szász G. Lipophilicity of amphoteric molecules expressed by the true partition coefficient. Int. J. Pharm. 113 (1995) 47-55
34. Mandić Z., and Gabelica V. Ionization, lipophilicity and solubility properties of repaglinide. J. Pharm. Biomed. Anal. 41 (2006) 866-871
35. Takács-Novák K., Noszal B., Hermecz I., Kereszturi G., Podányi B., and Szász G. Protonation equilibria of quinolone antibacterials. J. Pharm. Sci. 79 (1990) 1023-1028
36. Zapała L., and Kalembkiewicz J. Studies of the distribution of N-phenylanthranilic acid in two-phase systems: aromatic solvent-water. Talanta 69 (2006) 601-607
37. Zapała L., Kalembkiewicz J., and Szlachta J. Studies on the distribution of mefenamic acid in two-phase systems: aromatic solvent-water. Pol. J. Chem. 79 (2005) 1235-1244
38. Sekine T., and Hasegawaa Y. Solvent Extraction Chemistry (1977), Marcel Dekker, New York
39. Kalembkiewicz J., and Zapała L. Distribution of 2-chlorobenzoic acid in aliphatic alcohol-water two-phase systems. Pol. J. Chem. 70 (1996) 768-771
40. Kopacz S., Kalembkiewicz J., and Szantula J. Investigation on monomer-dimer equilibrium of benzoic acid for some organic solvents. Zh. Obshch. Khim. 54 (1984) 721-728
41. Kalembkiewicz J., and Zapała L. Distribution of 2-chlorobenzoic acid in two-phase systems aromatic solvent-water. Pol. J. Chem. 75 (2001) 1797-1800