Potentiometric Studies on the Protonation Constants and Solvation of Some a-Amino Acid Benzyl- and t-Butyl- Esters in Ethanol-Water Mixtures

To gain more information about the effect of solvent on a -amino acid benzyl- and t-butyl- esters, the stoichiometric protonation constants of 10 esters (glycine benzyl ester, L-alanine benzyl ester, L-valine benzyl ester, L-serine benzyl ester, glycine t-butyl ester, L-alanine t-butyl ester, L-valine t-butyl ester, L-leucine t-butyl ester, L-phenylalanine t-butyl ester and L-isoleucine t-butyl ester) in 20%-80% (v/v) ethanol-water mixtures were determined at an ionic strength of 0.10 M NaCl and at 25.0 \pm 0.1 °C under nitrogen atmosphere. A potentiometric method was used and the calculation of constants was carried out using the PKAS computer program. The logarithm of the protonation constants of the above-mentioned a -amino acid esters linearly decreased with increases in ethanol contents but the values that determined 80% ethanol did not follow this linear trend. The variation of these constants is discussed on the basis of specific solute-solvent interactions.

Potentiometric Studies on the Protonation Constants and Solvation of Some a-Amino Acid Benzyl- and t-Butyl- Esters in Ethanol-Water Mixtures

To gain more information about the effect of solvent on a -amino acid benzyl- and t-butyl- esters, the stoichiometric protonation constants of 10 esters (glycine benzyl ester, L-alanine benzyl ester, L-valine benzyl ester, L-serine benzyl ester, glycine t-butyl ester, L-alanine t-butyl ester, L-valine t-butyl ester, L-leucine t-butyl ester, L-phenylalanine t-butyl ester and L-isoleucine t-butyl ester) in 20%-80% (v/v) ethanol-water mixtures were determined at an ionic strength of 0.10 M NaCl and at 25.0 \pm 0.1 °C under nitrogen atmosphere. A potentiometric method was used and the calculation of constants was carried out using the PKAS computer program. The logarithm of the protonation constants of the above-mentioned a -amino acid esters linearly decreased with increases in ethanol contents but the values that determined 80% ethanol did not follow this linear trend. The variation of these constants is discussed on the basis of specific solute-solvent interactions.

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  • G. Kort¨um, W. Vogel, K. Andrussow, Dissociation Constants of Organic Acids in Aqueous Solution, Plenium, New York, 1961.
  • V. Palm, Tables of Rate and Equilibrium Constants of Heterolytic Organic Reactions, Ed.; Moscow- Tartu, 1975-1985.
  • K. Izutsu, Acid-base Dissociation Constants in Dipolar Aprotic Solvents; IUPAC Chemical Data Series No: 35; Blackwell ScientiŞc: Oxford, 1990.
  • F.G. Bordwell, Acc. Chem. Res., 21, 456 (1988).
  • S.H. Herbert, C.M. Birdsall, J. Am. Chem. Soc. 65, 54 (1943).
  • B. Nowak, Z. Pawlak, J. Chem. Soc. Faraday Trans. I, 78, 2693 (1982)
  • G. Wada, E. Tamura, M. Okina and M. Nakamura, Bull. Chem. Soc. Jpn. 55, 3064 (1982).
  • F. K¨oseo˘glu, E. Kılı¸c and A. Do˘gan, Anal. Biochem. 277, 243 (2000).
  • D.L. Hughes, J.J. Bergan and E.J.J. Grabowski, J. Org. Chem. 55, 2579 (1986).
  • E.R. Benesch and R. Benesch, J. Am. Chem. Soc. 77, 5877 (1955).
  • J.T. Edsall, M.H. Blanchard, J. Am. Chem. Soc. 55, 2337 (1933).
  • D.D. Perrin, W.L.F. Armerega, PuriŞcation of Laboratory Chemicals, 1stedn, Pergamon, Oxford, 1966.
  • G. Gran, Acta. Chem. Scand. 4, 559 (1950) G. Gran, Analyst, 77, 661 (1952).
  • A.E. Martell and R.J. Motekaitis, The Determination and Use of Stability Constants, VCH, Weinheim, M. Meloun, J. Havel and H. H¨ogfelt, Computation of Solution Equilibria, Wiley, New York, 1988.
  • E.M. Woolley, D.G. Hurkot and L.G. Hepler, J. Phys. Chem. 74, 3908 (1970).
  • R. J Motekaitis, A.E Martell, Can. J. Chem., 60, 168 (1982).
  • E. Kılı¸c, G. G¨ok¸ce and E. Canel, Turk. J. Chem. 26, 843 (2002).
  • E. Kılı¸c, F. K¨oseo˘glu and ¨O. Ba¸sgut, Anal. Chim. Acta. 294, 215 (1994).
  • M.S.K. Niazi and J. Mollin, Bull. Chem. Soc. Jpn. 60, 2605 (1987).
  • C.C Panichajakul and E.M. Woolley, Anal. Chem. 47, 1880 (1975).
  • H. Irving and H. Rossotti, Acta. Chem. Scand. 10, 72 (1986).
  • H. Irving and H. Rossotti, Analyst, 80, 245 (1955).
  • P.S. Gentile, M. Cefole and A.V. Celiano, J. Phys. Chem. 67, 1447 (1963).
  • M. Paabo, R.G. Bates and R.A. Robinson, J. Phys. Chem. 70, 247 (1965).
  • R.G. Bates, J. Electroanal. Chem. 29, 1 (1971).
  • A.K. Chattopadhyay and S.C. Lahiri, Electrochim. Acta. 27, 269 (1982).
  • N.S. Isaacs, Physical Org. Chem. Longman, New York, 1986.
  • R.G. Bates, Determination of pH, Theory and Practice, 2ndedn., Wiley, New York, 1973.
Turkish Journal of Chemistry-Cover
  • ISSN: 1300-0527
  • Yayın Aralığı: Yılda 6 Sayı
  • Yayıncı: TÜBİTAK
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