Solvent effect on protonation constants of 5, 10, 15, 20-Tetrakis(4- sulfonatophenyl)porphyrin in different aqueous solutions of methanol and ethanol

Journal of Solution Chemistry

Volumn 39, Issue 2, 2010, Pages 231-244

  Farjtabar, Ali ^a   Gharib, Farrokh ^a  

^a SHAHID BEHESHTI UNIVERSITY   (Iran)

Author keywords

5,10,15,20 tetrakis(4 sulfonatophenyl) porphyrin; Aqueous solutions of methanol and ethanol; Protonation constant; Solvent effect

Indexed keywords

EID: 77952429661     PISSN: 00959782     EISSN: None     Source Type: Journal    
DOI: 10.1007/s10953-010-9496-y     Document Type: Article

References (45)

1. P. Rothemund 1936 A new porphyrin synthesis. The synthesis of porphin J. Am. Chem. Soc. 58 625 627 10.1021/ja01295a027 1:CAS:528:DyaA28XivFSmuw%3D%3D
2. Longo, F.R., Brown, E.M., Rew, W., Adler, A.D.: The Porphyrins. Academic Press, New York (1980)
3. D.K. Lavallee 1985 Kinetics and mechanisms of metalloporphyrin reactions Coord. Chem. Rev. 61 55 96 10.1016/0010-8545(85)80002-3 1:CAS:528: DyaL2MXhtlynsro%3D
4. D. Brault 1990 Physical chemistry of porphyrins and their interactions with membranes: the importance of pH J. Photochem. Photobiol. B, Biol. 6 79 86 10.1016/1011-1344(90)85076-9 1:CAS:528:DyaK3cXlt1yluro%3D
5. T. Makino 1999 A simple and sensitive colorimetric assay of zinc in serum using cationic porphyrin Clin. Chim. Acta 282 65 76 10.1016/S0009-8981(99) 00012-1 1:CAS:528:DyaK1MXit1Wrsrc%3D (Pubitemid 29179472)
6. Milgrom, L.R.: The Colors of Life: An Introduction to the Chemistry of Porphyrins and Related Compounds. Oxford University Press, Oxford (1997)
7. 2O on the photophysical properties of meso-tetra (4-sulphonatophenyl) porphine, Photosan III and tetrasulphonated aluminium and zinc phthalocyanines J. Phochem. Photobiol. A, Chem. 78 215 219 10.1016/1010-6030(93)03730-5 1:CAS:528: DyaK2cXjtFWitLs%3D
8. J. Mosinger M. Deumie K. Lang P. Kubat D.M. Wagnerova 2000 Supramolecular sensitizer: Complexation of meso-tetrakis(4-sulfonatophenyl)porphyrin with 2-hydroxypropyl-cyclodextrins J. Photochem. Photobiol. A, Chem. 130 13 20 10.1016/S1010-6030(99)00204-X 1:CAS:528:DyaK1MXnsF2hsL4%3D
9. B. Cunderlikova L. Gangeskar J. Moan 1999 Acid-base properties of chlorin e6: relation to cellular uptake J. Photochem. Photobiol. B, Biol. 53 81 90 10.1016/S1011-1344(99)00130-X 1:CAS:528:DC%2BD3cXhtlCisL0%3D (Pubitemid 30047590)
10. I.F. Tannock D. Rotin 1989 Acid pH in tumors and its potential for therpeutic exploitation Cancer Res. 49 4373 4384 1:STN:280:DyaL1MzgtlymtA%3D%3D
11. J.L. Wike-Hooley J. Haveman J.S. Reinhold 1984 The relevance of tumour pH to the treatment of malignant disease Radiother. Oncol. 2 343 366 10.1016/S0167-8140(84)80077-8 1:STN:280:DyaL2M7hsVWjuw%3D%3D
12. H. Brunner M.R. Arndt B. Treittinger 2004 Porphyrin platinum conjugates-new aims Inorg. Chim. Acta 357 1649 1669 10.1016/S0020-1693(03)00479- 1 1:CAS:528:DC%2BD2cXislyjsb4%3D
13. E.B. Fleischer J.M. Palmer T.S. Srivastava A. Chatterjee 1971 Thermodynamic and kinetic properties of an iron porphyrin system J. Am. Chem. Soc. 93 3162 3165 10.1021/ja00742a012 1:CAS:528:DyaE3MXksFertrw%3D
14. P. Gameiro S. Reis J.L.F.C. Lima B. de Castro 2000 Calibration of pH glass electrodes by direct strong acid/strong base titrations under dilute conditions Anal. Chim. Acta 405 167 172 10.1016/S0003-2670(99)00641-8 1:CAS:528:DC%2BD3cXhtVajsb0%3D (Pubitemid 30017897)
15. J.S. Jaime-Ferrer E. Couallier M. Rakib G. Durand 2007 Electrochemical determination of acidity level and dissociation of formic acid/water mixtures as solvent Electrochim. Acta 52 5773 5780 10.1016/j.electacta.2007.02.058 (Pubitemid 46680340)
16. J.L. Beltran R. Codony M.D. Prat 1993 Evaluation of stability constants from multi-wavelength absorbance data: program STAR Anal. Chim. Acta 276 441 454 10.1016/0003-2670(93)80415-H 1:CAS:528:DyaK3sXisVWqtL0%3D (Pubitemid 23113687)
17. R.F. Pasternack L. Francesconi D. Raff E. Spiro 1973 Aggregation of nickel(II), copper(II), and zinc(II) derivatives of water-soluble porphyrins J. Am. Chem. Soc. 95 2606 2611 10.1021/ja00794a604
18. I.D. Satteriee A. Shelnutt 1984 Studies of urohemin-I in aqueous-solution, thermodynamics of self-association and elerctronic- propertities of 2 species detected by proton nmr-spectroscopy J. Phys. Chem. 88 5487 5492 10.1021/j150667a008
19. T.K. Chandrashekar H. Van-Willigen M.H. Ebersole 1984 Optical and electron-spin resonance study of cation and cation crown ether induced dimerization of tetrakis(4-sulfonatophenyl)porphyrin J. Phys. Chem. 88 4326 4332 10.1021/j150663a027 1:CAS:528:DyaL2cXltF2ltbk%3D
20. K. Kano T. Nakajima M. Takei S. Hashimoto 1987 Self aggregation of cationic porphyrin in water Bull. Chem. Soc. Jpn. 60 1281 1287 10.1246/bcsj.60.1281 1:CAS:528:DyaL1cXjslCltA%3D%3D
21. Beck, M.T., Nagypal, I.: Chemistry of Complex Equilibria. Ellis Harwood, New York (1990)
22. A. Farajtabar F. Gharib P. Jamaat N. Safari 2008 Complexation of 5,10,15,20-tetrakis(4-sulfonatophenyl)porphyrin with zinc(II) ions in aqueous solution J. Chem. Eng. Data 53 350 354 10.1021/je7003676 1:CAS:528: DC%2BD1cXhsFKrsg%3D%3D (Pubitemid 351488348)
23. Tabata, M., Tanaka, M.: A new method for the determination of the stability constant of metalloporphyrins, use of the catalytic effect of mercury(II) on metalloporphyrin formation. J. Chem. Soc. Chem. Commun., 42-43 (1985)
24. R. Okumura T. Hinoue H. Watarai 1996 Ion-association adsorption of water-soluble porphyrin at a liquid-liquid aqueous systems Anal. Sci. 12 393 397 10.2116/analsci.12.393 1:CAS:528:DyaK28XjsFOqt7g%3D
25. 3: spectroscopic and ab initio study New J. Chem. 28 1600 1607 10.1039/b310909g 1:CAS:528:DC%2BD2cXhtVGqur3E (Pubitemid 38869830)
26. H. Baker L. Wagner P. Hambright 1973 Metal ion porphyrin interactions. Evidence for nonexistence of sitting atop complexes in aqueous solution J. Am. Chem. Soc. 95 5942 5946 10.1021/ja00799a019 1:CAS:528:DyaE3sXltVyksL0%3D
27. J. Barbosa D. Barron J.L. Beltran S. Buti 1998 On the role of solvent in acid-base equilibria of diuretics in acetonitrile-water mixed solvents Talanta 45 817 827 10.1016/S0039-9140(97)00167-7 1:CAS:528:DyaK1cXhtlaqs7g%3D (Pubitemid 28111355)
28. J. Barbosa I. Toro V. Sanz-Nebot 1997 Acid-base behavior of tripeptides in solvent used in liquid chromatography. Correlation between pK values and solvatochromic parameters of acetonitrile-water mixtures Anal. Chim. Acta 347 295 304 10.1016/S0003-2670(97)00163-3 1:CAS:528:DyaK2sXktl2nsrY%3D (Pubitemid 27351364)
29. H. Demirelli 2005 On the role of the solvent and substituent on the protonation equilibria of di-substituted anilines in dioxane-water mixed solvents J. Sol. Chem. 34 1283 1295 10.1007/s10953-005-8020-2 1:CAS:528:DC%2BD2MXht1Knt7bK (Pubitemid 41738332)
30. Isutsu, K.: Electrochemistry in Nonaqueous Solutions. Wiley-VCH, Weinheim (2002)
31. Reichardt, C.: Solvents and Solvent Effects in Organic Chemistry, 3rd edn. Wiley-VCH, Weinheim (2004)
32. R.W. Taft J.L.M. Abboud M.J. Kamlet 1984 Linear solvation energy relationships. 28. An analysis of Swain's solvent "acidity" and "basicity" scales J. Org. Chem. 49 2001-2005 10.1021/jo00185a034
33. M.J. Kamlet J.L.M. Abboud M.H. Abraham R.W. Taft 1983 Linear solvation energy relationships. 23. A comprehensive collection of the solvatochromic parameters, π *,α, and β, and some methods for simplifying the generalized solvatochromic equation J. Org. Chem. 48 2877 2887 10.1021/jo00165a018 1:CAS:528:DyaL3sXkvVOgsbc%3D
34. F. Gharib M. Jabbari A. Farajtabar A. Shamel 2008 Solvent effects on protonation and complexation of glutamic and aspartic acids with molybdenum(VI) in different aqueous solutions of methanol J. Chem. Eng. Data 53 1772 1778 10.1021/je800106j 1:CAS:528:DC%2BD1cXosF2gurg%3D
35. F. Gharib 2005 Solvent effects on complexation of dioxovanadium(V) with penicillamine in methanol-water mixtures J. Chem. Eng. Data 50 196 200 10.1021/je049737k 1:CAS:528:DC%2BD2cXhtVOhsLvJ (Pubitemid 40122530)
36. F. Gharib F. Sadeghi 2007 Solvent Effects on complexation of thallium(I) with guanosine 5′-monophosphate in methanol-water mixtures Appl. Organomet. Chem. 21 218 225 10.1002/aoc.1211 1:CAS:528:DC%2BD2sXktVSmurg%3D (Pubitemid 46473408)
37. N. Maleki B. Haghighi A. Safavi 1999 Evaluation of formation constants, molar absorptivities of metal complexes, and protonation constants of acids by nonlinear curve fitting using Microsoft Excel Solver Micochem. J. 62 229 236 10.1006/mchj.1998.1665 1:CAS:528:DyaK1MXjtFKht78%3D
38. U. Buhvestov F. Rived C. Rafols E. Bosch M. Roses 1998 Solute-solvent and solvent-solvent interactions in binary solvent mixtures, part 7: comparison of the enhancement of the water structure in alcohol-water mixtures measured by solvatochromic indicators J. Phys. Org. Chem. 11 185 192 10.1002/(SICI)1099- 1395(199803)11:3<185::AID-POC993>3.0.CO;2-5 1:CAS:528:DyaK1cXisFSgs74%3D
39. G. Akerlof 1932 Dielectric constants of some organic solvent-water mixtures at various temperatures J. Am. Chem. Soc. 54 4125 4139 10.1021/ja01350a001 1:CAS:528:DyaA3sXmtlyq
40. G. Moger 1995 Solvent effect on the dissociation constants and Soret band maxima of hematoporphyrin diacid React. Kinet. Catal. Lett. 54 329 336 10.1007/BF02071027 1:CAS:528:DyaK2MXlvFSlt74%3D
41. J. Barbosa G. Fonrodona I. Marques S. Buti I. Toro 1997 Factor analysis applied to the correlation between dissociation constants and solvatochromic parameters in water-acetonitrile mixtures, II: Study of solvent effects on the dissociation of functional groups of diuretics, quinolones, buffers and peptides Trends Anal. Chem. 16 104 111 10.1016/S0165-9936(96)00101-X 1:CAS:528:DyaK2sXhvVGksLw%3D (Pubitemid 27107870)
42. M. Yasuda 1959 Dissociation constants of some carboxylic acids in mixed aqueous solvents Bull. Chem. Soc. Jpn. 32 429 432 10.1246/bcsj.32.429 1:CAS:528:DyaF3cXhsVKktQ%3D%3D
43. Shedlovsky, T.: In: Peasce, B. (ed.) Electrolytes. Pergamon, New York (1962)
44. a of insoluble basic drugs containing amino groups J. Pharm. Sci. 92 1473 1481 10.1002/jps.10415 1:CAS:528: DC%2BD3sXltlWgsrY%3D (Pubitemid 36792759)
45. A. Avdeef K.J. Box J.E.A. Comer M. Gilges M. Hadley C. Hibbert W. Patterson K.Y. Tam 1999 PH-metric log∈P11. pK(a) determination of water-insoluble drugs in organic solvent-water mixtures J. Pharm. Biomed. Anal. 20 631 641 10.1016/S0731-7085(98)00235-0 1:CAS:528:DyaK1MXktVCgur4%3D (Pubitemid 29245964)