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.

About the authors

G. P. Zharkov

Ural Federal University, the first President of Russia B.N. Yeltsin; Ural Research Institute of Metrology, branch of the Federal State Unitary Enterprise “VNIIM named after D. Mendeleev”

Email: gennady.zharkov@mail.ru
st. Mira, 19, Ekaterinburg, 620002 Russia; st. Krasnoarmeyskaya, 4, Ekaterinburg, 620075 Russia

N. N. Yunusov

Ural Federal University, the first President of Russia B.N. Yeltsin

Email: gennady.zharkov@mail.ru
st. Mira, 19, Ekaterinburg, 620002 Russia

Yu. S. Petrova

Ural Federal University, the first President of Russia B.N. Yeltsin

Email: gennady.zharkov@mail.ru
st. Mira, 19, Ekaterinburg, 620002 Russia

A. V. Pestov

Ural Federal University, the first President of Russia B.N. Yeltsin; Institute of Organic Synthesis, Russian Academy of Sciences, AND I. Postovsky Ural Branch of the Russian Academy of Sciences

Email: gennady.zharkov@mail.ru
st. Mira, 19, Ekaterinburg, 620002 Russia; st. Akademicheskaya, 20, Ekaterinburg, 620990 Russia

L. K. Neudachina

Ural Federal University, the first President of Russia B.N. Yeltsin

Author for correspondence.
Email: gennady.zharkov@mail.ru
st. Mira, 19, Ekaterinburg, 620002 Russia

References

  1. Litecká M., Gyepes R., Vargová Z. et al. // J. Coord. Chem. 2017. V. 70. № 10. P. 1698. https://doi.org/10.1080/00958972.2017.1305493
  2. Ali S., Singh V., Jain P. et al. // J. Saudi Chem. Soc. 2019. V. 23. № 1. P. 52. https://doi.org/10.1016/j.jscs.2018.04.005
  3. Desai N.C., Makwana A.H., Senta R.D. // J. Saudi Chem. Soc. 2016. V. 20. № 6. P. 686. https://doi.org/10.1016/j.jscs.2015.01.0043
  4. Kumar K., Murugesan S. // J. Saudi Chem. Soc. 2018. V. 22. № 1. P. 16. https://doi.org/10.1016/j.jscs.2017.05.012
  5. Samsonowicz M., Regulska E., Kalinowska M. // Chem.-Biol. Interact. 2017. V. 273. P. 245. https://doi.org/10.1016/j.cbi.2017.06.016
  6. Gacki M., Kafarska K., Pietrzak A. et al. // J. Saudi Chem. Soc. 2019. V. 23. № 3. P. 346. https://doi.org/10.1016/j.jscs.2018.08.006
  7. Nawaz M., Abbasi M.W., Hisaindee S. et al. // Spectrochim. Acta, Part A: Mol. Biomol. Spectrosc. 2016. V. 161. P. 39. https://doi.org/10.1016/j.saa.2016.02.022
  8. Nawaz M., Almessiere M.A., Almofty S.A. et al. // J. Photochem. Photobiol. B. 2019. V. 196. P. 111506. https://doi.org/10.1016/j.jphotobiol.2019.05.003
  9. Gupta G.K., Sharma S.K., Ramteke R. // J. Phytopathol. 2012. V. 160. № 4. P. 167. https://doi.org/10.1111/j.1439-0434.2012.01884.x
  10. Неудачина Л.К., Осинцева Е.В., Скорик Ю.А. и др. // Журн. аналит. химии. 2005. Т. 60. № 3. С. 271.
  11. Скорик Ю.А., Неудачина Л.К., Коротовских Е.В. и др. // Завод. лаб. 2001. Т. 67. № 3. С. 15.
  12. Печищева Н.В., Осинцева Е.В., Неудачина Л.К. и др. // Докл. РАН. 2006. Т. 408. № 2. С. 199.
  13. Осинцева Е.В., Неудачина Л.К., Амфитеатрова А.В. и др. // Завод. лаб. 2006. Т. 72. № 9. С. 11.
  14. Nawaz M., Abbasi M.W., Tariq M. et al. // BMC Chem. 2022. V. 16. № 1. P. 21. https://doi.org/10.1186/s13065-022-00817-x
  15. Solov’ev V.P., Tsivadze A.Yu. // Prot. Met. Phys. Chem. Surf. 2015. V. 51. № 1. P. 1. https://doi.org/10.1134/S2070205115010153
  16. Zharkov G.P., Filimonova O.V., Petrova Yu.S. et al. // Russ. Chem. Bull. 2022. V. 71. № 1. P. 152. https://doi.org/10.1007/s11172-022-3389-2
  17. Zharkov G.P., Filimonova O.V., Petrova Yu.S. et al. // Russ. J. Inorg. Chem. 2023. V. 68. № 8. P. 988. https://doi.org/10.1134/S0036023623601058
  18. Zharkov G.P., Bueva E.I., Filimonova O.V. et al. // Russ. J. Inorg. Chem. 2023. V. 68. № 4. P. 466. https://doi.org/10.1134/S0036023623600247
  19. Электронный ресурс / https://chemaxon.com/marvin
  20. Wallace R.M., Katz S.M. // J. Phys. Chem. 1964. V. 68. № 12. P. 3890. https://doi.org/10.1021/j100794a511
  21. Хартли Ф.Р., Бёргес К., Олкок Р.М. Равновесия в растворах. М.: Мир, 1983.
  22. Lu T.-H., Chattopadhyay P., Liao F.-L. et al. // Anal. Sci. 2001. V. 17. № 7. P. 905. https://doi.org/10.2116/analsci.17.905
  23. Бек М., Надьпал И. Исследование комплексообразования новейшими методами. М.: Мир, 1989.
  24. NIST Critically Selected Stability Constants of Metal Complexes, Version 8.0, 2004.
  25. Irving H., Williams R.J.P. // J. Am. Chem. Soc. 1953. P. 3192. https://doi.org/10.1039/jr9530003192
  26. Haynes W.M. // CRC Handbook of Chemistry and Physics, 95th Edition. Hoboken: CRC Press, 2014.
  27. Weast R.C. // CRC Handbook of Chemistry and Physics, 57th Edition. Cleveland: CRC Press, 1976.

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