Abstract
Some new ternary complexes’ [Cu(II), Ni(II), Co(II), and Zn(II)] metal ions with phenylephrine and some selected carboxylic acid were investigated by means of potentiometry techniques at 25 °C and in I = 0.10 mol L−1 NaNO3. The protonation equilibria of phenylephrine and biologically important aliphatic and aromatic carboxylic acids: adipic, succinic, malic, tartaric, oxalic, phthalic, and salicylic were investigated and discussed. The acidity constants of the ligand under study were determined and used for determining the stability constants of the binary and ternary complexes formed in the aqueous medium under the experimental conditions. The order of stability constants of binary and ternary complexes was found to obey Co(II) < Ni(II) < Cu(II) > Zn(II). The ternary complex formation was found to occur in a stepwise manner. Extrastability of ternary complexes compared to their binary complexes was explained to be due to electrostatic interactions of the side chains of ligands, charge neutralization, chelate effect, stacking interactions, and hydrogen bonding. The relative stabilities of the ternary complexes are compared with those of the corresponding binary complexes in terms of (ΔlogK, \(\log X\) and % R. S) values. The concentration distribution of the various complex species in solution was evaluated and discussed.
Similar content being viewed by others
References
C. Moffat, J.V. Jackson, M.S.D. Moss, Clarke’s Isolation and Identification of Drugs (The pharmaceutical press, London, 1986)
T.N. Al-Sabha, Pak. J. Anal. Environ. Chem. 1, 1 (2010)
A.Y. Louie, T.J. Meade, Chem. Rev. 99, 2711 (1999)
R.N. Patel, N. Singh, K. Shukla, U.K. Chauhan, S. Chakraborty, J.N. Gutierrez, A. Castineiras, J. Inorg. Biochem. 98, 231 (2004)
A.H. Fairlamb, G.B. Henderson, A. Cerami, Proc. Natl. Acad. Sci. USA 86, 2607 (1989)
Z. Balcarova, J. Kasparakova, A. Zakovska, O. Novakova, M.F. Sivo, G. Natile, V. Brabeck, Mol. Pharmacol. 53, 846 (1998)
R.L. La Femina, J. Virol. 66, 7414 (1992)
P.S. Moore, C.J. Jones, J. Biochem. 307, 129 (1995)
O. Rixe, W. Ortuzar, M. Alvarez, R. Parker, E. Reed, K. Paull, T. Fojo, Biochem. Pharmacol. 52, 1855 (1996)
R. Bakhtiar, E.I. Ochiai, Gen. Pharmacol. 32, 525 (1999)
H.H. Hammud, G. Nemer, W. Sawma, J. Touma, P. Barnabe, Y. Bou-Mouglabey, A. Ghannoum, J. El-Hajjar, J. Usta, Chem. Biol. Interact. 173, 84 (2008)
E. Martell, R.M. Smith, Critical Constants-1: Amino acids (New York, 1974)
H. Sigel, Metal Ions in Biological Systems-2 (Marcel-Dekker Inc, New York, 1973)
M.T. Beck, Chemistry of Complex Equilibria, (Van Nostrand, New York, 1970) p. 174
A.L. Lehninger, Phys. Rev. 30, 393 (1950)
F.M. Richards, H.M. Wyckoff, N.M. Allewel, Neurosciences 901, (1969)
W.R. Harris, L. Messori, Coord. Chem. Rev. 228, 237 (2002)
P.J. Sadler, Z. Gun, Pure Appl. Chem. 70, 863 (1998)
P.J. Sadler, Adv. Inorg. Chem. 36, 1 (1991)
M.J. Abrams, B.A. Murrer, Science 261, 725 (1993)
A.E. Martell, M. Calvin, Chemistry of Metal Chelate Compounds (Prentie Hall, Inc., Englad, Cliffs, N.J., 1962)
R.A. Ammar, A. Nafady, M.F. Amin, M.M. Al-Mogren, M.E. Shoukry, Int. J. Electrochem. Sci. 8, 1501 (2013)
A.K. Banerjee, T.V. Rao, J. Indian Chem. Soc. 63, 480 (1968)
H. Irving, R.J.P. William, J. Chem. Soc 3192 (1953)
F.J. Welcher, The Analytical Uses of Ethylenediaminetetraacetic Acid (Von Nostrand, Princeton, NJ, 1965)
H.M. Irving, H.S. Rossotti, J. Chem. Soc 3397, 2904 (1953–1954)
P. Gans, O. Sullivan, B. Glee, Talanta 51, 33 (2000)
P. Gans, A. Sabatini, Vacca. Talanta 43, 1739 (1996)
R.G. Bates, Determination of pH-Theory and Practice, 2nd edn. (Wiley-Interscience, New York, 1975)
SC Database; Royal Society of Chemistry; IUPAC: 2004. http://www.Acadsoft.Co.uk/
R. Cornelis, J. Caruso, H. Crews, K. Heumann, Handbook of Elemental Speciation: Techniques and Methodology (Wiley, New York, 2003)
M.M. Shoukry, A.A. Shoukry, P.A.K. Alla, S.S. Hassan, Int. J. Chem. Kinet. 42, 608 (2010)
J. Inezedy, Determination of equilibrium constants, in Analytical Applications of Omplex Equilibria, ed. by S. Ellis (Ellis Howard, Chichester, UK, 1967)
R.M. Smith, A.E. Martell, NIST critically selected stability constants of metal complexes database, Version 3.0. NIST Standard Reference Database 46, U.S. Department of Commerce, (National Institute of Standard and Technology (1997)
A.A. Boraei, N.F.A. Mohamed, J. Chem. Eng. 47, 987 (2002)
M.M. Shoukry, S.M.T. Ezzat, Bioinorgan. Chemistry Appl 1 (2014)
H.A. Azab, A.M. Nady, A. Hassan, R.S.A. Azkal, J. Chem. Eng 38, 502 (1993)
R. Weast, Handbook of Chemistry and Physics, 68th edn. (CRC Press, Boca Raton, FL, 1987)
M.F. Amin, J. Chem. Chem. Eng. 7, 591 (2013)
H.A. Ewais, M. Taha, H.N. Salm, J. Chem. Eng. Data 55, 754 (2010)
B. Humbert, M. Alnot, F. Quile`s, F. Infrared, A. Raman, J. Chromatogr. 54, 465 (1998)
F. Mack, H. Bonisch, Naunyn-Schmiedeberg’s Arch. Pharmacol 310, 1 (1979)
M. Meloun, T. Syrový, A. Vrána, Anal. Chem. Acta 533(1), 97 (2005)
S. Riegelman, L.A. Strait, E.Z. Fischer, J. Pharm. Sci. 51, 2 (1962)
H.A. Azab, A.M. Nady, A. Hassan, R.S.A. Azkal, Monatsshefte fṻr Chemie 124, 267 (1993)
G.V. Mane, D.G. Kolhatkar, L.P. Shinde, J. Chem. Pharm. Res. 4(2), 1022 (2012)
P.D. Manwel, Asian J. Chem. 6(2), 408 (1994)
S.A.A. Sajadi, Adv. Biosc. Biotechnol. 1, 354 (2010)
M.M. Khalil, A. Radalla, F. Qasem, R. Khaled, J. Korean Chem. Soc. 31(1), 109 (2014)
K. Irving, R.P. Williams, Nature (London) 162, 746 (1948)
H.M.N.H. Irving, R.J.P. Williams, The stability of transition-metal complexes. J. Chem. Soc. (pp. 3192–3210, 1952)
J.E. Huheey, Inorganic Chemistry-Principles of Structure and Reactivity (Harper, New York, NY, USA, 1983)
F.A. Cotton, G. Wilkinson, Advaned Inorganic Chemistry (Wiley, London, UK, 1962)
C.S.G. Phillips, R.J.P. Williams, Inorganic Chemistry: Metals, vol. 2 (Oxford University Press, New York, NY, USA, 1966)
H. Sigel, Angew. Chem. Int. Edn. 14, 394 (1975)
H. Sigel, B.E. Fischer, E. Farkas, Inorg. Chem. 22, 925 (1983)
B.E. Fischer, H. Sigel, Inorg. Chem. 18(2), 425 (1979)
R.B. Martin, R.J. Prados, J. Inorg. Nucl. Chem. 36, 1665 (1974)
G.F. Condike, A.E. Martell, J. Inorg. Nucl. Chem. 31, 2455 (1969)
S. Singh, A.K. Ghose, J. Indian Chem. Soc. 73, 650 (1996)
S. Tyagi, S. Gencaslan, U.P. Singh, J. Chem. Eng. Data 48, 925 (2003)
R. Dewitt, J.L. Watters, J. Am. Chem. Soc. 76, 3810 (1954)
S. Kida, Bull. Chem. Soc. Jpn. 29, 805 (1956)
Author information
Authors and Affiliations
Corresponding author
Rights and permissions
About this article
Cite this article
Khalil, M.M., Mahmoud, R.K. pH-metric studies of acid–base equilibria on the mixed M(II) complexes with R-3-[-1-hydroxy-2(methylamino)ethyl]phenol and some selected carboxylic acids. J IRAN CHEM SOC 12, 1149–1161 (2015). https://doi.org/10.1007/s13738-014-0576-6
Received:
Accepted:
Published:
Issue Date:
DOI: https://doi.org/10.1007/s13738-014-0576-6