Dissociation Constant of N-(2-Acetamido)-Iminodiacetic Acid Monosodium (ADA) from (278.15 to 328.15) K

Abstract

The acidic dissociation constant of N-(2-acetamido)-iminodiacetic acid monosodium (ADA) has been determined at 12 temperatures from 278.15 to 328.15 K by electromotive-force (emf) measurements of hydrogen-silver chloride cells without liquid junction. At 298.15 K, the value of the dissociation constant (pK2) is 6.8416 ± 0.0004. In response to the need for new physiological pH standards, buffer solutions of NaADA and its disodium salt, Na2ADA would be useful for pH control in the biological region of pH 6.5 to 7.5. The pK2 values over the experimental temperature range are given as a function of the thermodynamic temperature (T) by the equation pK2 = 2943.784/T - 47.05762 + 7.72703 ln T. At 298.15 K, standard thermodynamic quantities for the dissociation process have been derived from the temperature coefficients; ΔH° = 12,252 J·mol-1, ΔS° = -89.9 J·K-1·mol-1 and = -148 J·K-1·mol-1. The results are interpreted and compared with those of structurally related derivatives of GLYCINE.

Share and Cite:

Roy, R. , Roy, L. , Dinga, J. , Medcalf, M. , Hundley, K. , Hines, E. , Summers, C. , Tebbe, L. and Veliz, J. (2014) Dissociation Constant of N-(2-Acetamido)-Iminodiacetic Acid Monosodium (ADA) from (278.15 to 328.15) K. Open Journal of Physical Chemistry, 4, 73-79. doi: 10.4236/ojpc.2014.42011.

Conflicts of Interest

The authors declare no conflicts of interest.

References

[1] King, E.J. (1951) The Ionization Constants of Glycine and the Effects of Sodium Chloride upon Its Second Ionization. Open Journal of Physical Chemistry, 73, 155-159.
[2] Roy, R.N., Robinson, R.A. and Bates, R.G. (1973) Thermodynamics of the Two Dissociation Steps of N-Tris(hydroxymethymethylglycine (“Tricine”) in Water from 5?C to 55?C. Journal of the American Chemical Society, 95, 8231-8235. http://dx.doi.org/10.1021/ja00806a004
[3] Roy, L.N., Roy, R.N., Denton, C.E., LeNoue, S.R., Roy, C.N., Ashkenazi, S., Williams, T.B., Church, D.R., Fuge M.S. and Sreepada, K.N. (2006) Second Dissociation Constant of Bis-[(2-hydroxyethyl)amino]acetic Acid (BICINE) and pH of Its Butter Solutions from 5?C to 55?C. Journal of Solution Chemistry, 35, 605-624. http://dx.doi.org/10.1007/s10953-005-9009-6
[4] Roy, R.N., Roy, L.N., Simon, A.N., Moore, A.C., Seing, L.A., Richards, S.J., Craig, H.D., Childers, B.A., Tabor, B.J., Himes, C.A. and Viele, K.E. (2004) Thermodynamics of the Second Dissociation Constant of N-tris[Hydroxymethyl]4-aminobutanesulfonic Acid (TABS) from 5?C to 55?C. Journal of Solution Chemistry, 33, 353-364. http://dx.doi.org/10.1023/B:JOSL.0000036306.61494.e2
[5] Roy, R.N., Moore, C.P., Lord, P., Mrad, D., Good, W.S., Niederschmidt, J.A., Roy, L.N. and Kuhler, K.M. (1997) Thermodynamic Constants of N-(2-Hydroxyethyl) Piperazine-N’-3-Propanesulfonic Acid (HEPPS) and (3-[N-Morpholinol])-2-hydroxypropanesulfonic Acid (MOPSO) from the Temperatures 278.15 to 328.15 K. Journal of Chemical Thermodynamics, 29, 1323-1331.
http://dx.doi.org/10.1006/jcht.1997.0251
[6] Roy, R.N., Gibbons, J.J., Padron, J.L. and Casebolt, R.G. (1981) Thermodynamics of the Second-Stage Dissociation of N-(2-acetamido)iminodiacetic Acid in Water from 5?C to 55?C. Analytica Chimica Acta, 128, 247-252. http://dx.doi.org/10.1016/S0003-2670(01)84139-8
[7] Good, N.E., Winget, G.D., Winter, W., et al. (1966) Hydrogen Ion Buffers for Biological Research. Biochemistry, 5, 467-477. http://dx.doi.org/10.1021/bi00866a011
[8] Bates, R.G., Roy, R.N. and Robinson, R.A. (1973) Buffer Standards of Tris(Hydroxymethyl)methylglycine (“Tricine”) for the Physiological Range pH 7.2 to 8.5. Analytical Chemistry, 45, 1663-1666. http://dx.doi.org/10.1021/ac60331a022
[9] Gary, R., Bates, R.G. and Robinson, R.A. (1964) Thermodynamics of Solutions of Deuterium Chloride in Heavy Water from 5°C to 50°C. Journal of Physical Chemistry, 68, 1186-1190.
http://dx.doi.org/10.1021/j100787a037
[10] Bates, R.G. (1973) Determination of pH. 2nd Edition, Wiley & Sons, New York, Chapter 10.
[11] Roy, R.N., Roy, L.N., Denton, C., LeNoue, S., Fuge, M., Dunseth, C., Roy, C., Bwashi, A., Wollen, J. and De Armon, S. (2009) Buffer Standards for the Physiological pH of 3-[(1,1-Dimethyl-2-hydroxymethyl)amino]-2-hydroxypropanesulfonic Acid (AMPSO) from 9278.15 to 328.15 K. Journal of Chemical Engineering Data, 54, 428-435. http://dx.doi.org/10.1021/je8004563
[12] Harned, H.S. and Ehlers, R.W. (1932) The Dissociation Constant of Acetic Acid from 0° to 35° Centigrade. Journal of the American Chemical Society, 54, 1350-1357.
http://dx.doi.org/10.1021/ja01343a013
[13] Roy, L.N., Roy, R.N., Wollen, J., Harmon, M., Martin, M., Bodendorfer, B., Stegner, J. and Henson, I. (2011) Calculation of the pH of Buffer Solution of 2-[N-morpholino]ethanesulfonic Acid (MES) from 5?C to 55?C. Open Journal of Physical Chemistry, 1, 77-84. http://dx.doi.org/10.4236/ojpc.2011.13011
[14] Ives, D.J.G. and Moseley, P.G.N. (1975) Derivation of Thermodynamic Functions of Ionization from Acidic Dissociation Constants. Journal Chemical Society, 72, 1132-1143.
[15] Please, N.W. (1954) Estimation of the Variance of the Data Used in the Calculation of Dissociation Constants. Biochemistry Journal, 56, 196-201.
[16] Datta, S.P. and Grzybowski, A.K. (1958) The Second Acid Dissociations of Glycine, Sarcosine, and N,N-Dimethylglycine: Part 1 and 2. Transaction Faraday Society, 54, 1179-1194.
http://dx.doi.org/10.1039/tf9585401179
[17] Timimi, B.A. and Everett, D.H. (1968) The Thermodynamics of the Acid Dissociation of Some Amino-Alcohols in Water. Journal Chemical Society B, 1380-1386. http://dx.doi.org/10.1039/j29680001380
[18] Harned, H.S. and Owen, B.B. (1958) The Physical Chemistry of Electrolytic Solutions. 3rd Edition, Reinhold, New York.
[19] Reference 18, Chapter 15.
[20] Datta, S.P., Grzybowski, A.K. and Bates, R.G. (1964) Second Acid Dissociation of N,N-Di(2-hydroxyethyl)glycine and Related Thermodynamic Quantities from 5° to 55°. Journal of Physical Chemistry, 68, 275-280. http://dx.doi.org/10.1021/j100784a011
[21] Roy, L.N., Roy, R.N., Downs, Z.M., Bodendorfer, B.M., Veliz, J.A., Stegner, J.M., Henson, I.B. and Wollen, J.T. (2011) Buffer Standards for Physiological pH of the Buffer N-(2-Acetamido)-2-aminoethanesulfonic Acid from 5° to 55°. Open Journal of Physical Chemistry, 1, 118-123.
http://dx.doi.org/10.4236/ojpc.2011.13016

Copyright © 2023 by authors and Scientific Research Publishing Inc.

Creative Commons License

This work and the related PDF file are licensed under a Creative Commons Attribution 4.0 International License.