Protolytic and Complexing Properties of Some Isomeric Aromatic Amino Acids in Aqueous Solution

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Abstract

The protolytic and complexation properties of some isomeric aromatic amino acids in aqueous solution were studied by a combination of pH-potentiometric and UV-spectrophotometric titration methods at I = 0.1 mol/dm3 (KCl/NaClO4) and t = (25 ± 1)°С. The acid dissociation constants of ammonium (pKa0) and carboxyl groups (pKa1) in the structure of isomeric benzene-carboxylic amino acids were determined: anthranilic acid (L1), meta-aminobenzoic acid (L2) and para-aminobenzoic acid (L3); ammonium groups (pKa1) in the structure of isomeric benzenesulfonic amino acids: orthanilic acid (L4), methanilic acid (L5), sulfanilic acid (L6). It is shown that the basicity of the amino group in the structure of the reagents decreases in the series of isomers: meta-, para-, ortho-isomer. Despite the fact that ortho-isomers are characterized by lower basicity of the amino group, it is shown that their metal complexes have the highest stability. It was found that anthranilic acid exhibits selective properties towards copper(II) ions, and orthanilic acid – towards silver(I) ions. The spectral characteristics of metal complexes of isomeric benzenesulfonic amino acids with transition metal ions: silver(I), copper(II), nickel(II) and cobalt(II) have been determined.

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About the authors

G. P. Zharkov

Yeltsin Ural Federal University; Ural Research Institute of Metrology – a branch of the Mendeleev All-Russian Scientific Research Institute of Metrology

Author for correspondence.
Email: gennady.zharkov@mail.ru
Russian Federation, 19, Mir St., Ekaterinburg, 620002; 4, Krasnoarmeyskaya St., Ekaterinburg, 620075

N. N. Yunusov

Yeltsin Ural Federal University

Email: gennady.zharkov@mail.ru
Russian Federation, 19, Mir St., Ekaterinburg, 620002

Yu. S. Petrova

Yeltsin Ural Federal University

Email: gennady.zharkov@mail.ru
Russian Federation, 19, Mir St., Ekaterinburg, 620002

A. V. Pestov

Yeltsin Ural Federal University; Postovsky Institute of Organic Synthesis of the Ural Branch of the Russian Academy of Sciences

Email: gennady.zharkov@mail.ru
Russian Federation, 19, Mir St., Ekaterinburg, 620002; 20, Akademicheskaya St., Ekaterinburg, 620990

L. K. Neudachina

Yeltsin Ural Federal University

Email: gennady.zharkov@mail.ru
Russian Federation, 19, Mir St., Ekaterinburg, 620002

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2. Table 1_Fig. 1

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8. Fig. 1. Spectrophotometric titration profiles of the H-L1 system: a - λ = 275 nm; b - λ = 310 nm.

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9. Fig. 2. Schematic of acid dissociation of isomers of benzolcarboxylic (a) and benzolsulfonic amino acids (b).

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10. Fig. 3. Self-absorption spectra of particles in the systems H-L2 (a) and H-L3 (b): 1 - L, 2 - HL, 3 - H2L.

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