SYNTHESIS OF QUATERNARY ARYLAMMONIUM SALTS OF PICOLINE ACID
Quaternary arylammonium salts were synthesized from the reactions of picolinic acid with aniline, isomeric nitroanilines and
aminophenols. The influence of the nature of the solvent on the course of the reactions was studied. Picolinic acid was found to
react with aromatic amines in ethanol at room temperature to form quaternary ammonium salts. The physical constants of the
synthesized salts were determined, and their structure was studied and confirmed by IR spectroscopy.
1. Yoshida T., Kawamura S., Nakata K. Chemoselective N-acetylation of primary aliphatic amines promoted by pivalic or acetic acid using
ethyl acetate as an acetyl donor // Tetrahedron Letters (2017).
2. Angus A.L., Lanny S.L. Carboxyl activation via silylthioesterification: one-pot, two-step amidation of carboxylic acids catalyzed by non-
metal ammonium salts // Tetrahedron Letters 56 (2015). -Р. 6034–6037.
3. Mokhov V.M., Popov Y.V., Budko I.I. Colloid and Nano-Sized Catalysts in Organic Synthesis: X.1 Synthesis of Carboxamides by Direct
Amidation of Carboxylic Acids and Transamidation Catalyzed by Colloid Copper // Russian Journal of General Chemistry, 2015, Vol. 85,
No. 4, -P. 820–826.
4. Charville H., Jackson D.A., Hodges G., Whiting A., Wilson M.R. The Uncatalyzed Direct Amide Formation Reaction – Mechanism
Studies and the Key Role of Carboxylic Acid H-Bonding // Eur. J. Org. Chem. 2011, -Р. 5981–5990.
5. Haussuhl S., Schreuer J. Crystal structure, elastic properties and phase transition of triclinic ammonium hydrogen succinate, NH 4 HC 4 H 4 О 4
// Zeitschrift fur Kristallographie 206, -Р. 255-265 (1993).
6. Rakhmanko E.M., Starobinets G.L., Yegorov V.V., Gulevich A.L., Lestchev S.M., Borovski E.S., Tsyganov A R. Analytical application of
high-molecular quaternary ammonium salts // Fresenius Z Anal Chem (t 989) 335:104-110. Springer-Verlag 1989.
7. Sprakel L.M.J., Schuur B. Solvent developments for liquid-liquid extraction of carboxylic acids in perspective // Separation and
Purification Technology 211 (2019), -Р. 935–957.
8. Yuvchenko A.P. et al. Synthesis and Properties of Functionally Substituted Ammonium Salts of 3-tert-Butylperoxy-3-methylbutanoic
Acid // Russian Journal of General Chemistry, Vol. 75, No. 9, 2005, -P. 1421-1429. 2005 Pleiades Publishing, Inc.
9. Lemmerer A. Two-Dimensional Layers Using Different Combinations of Hydrogen Bonded Rings in Three Ammonium Carboxylate Salts
// J Chem Crystallogr (2012) 42: -Р. 338–344.
10. Jin S. et al. Salt and co-crystal formation from 6-bromobenzo[d]thiazol-2-amine and different carboxylic acid derivatives // Journal of
Molecular Structure, 1016 (2012), -Р. 55–63.
11. Jin S., Wang D., Zhu H., Zhou Y., Li D., Ren J. Crystal and Molecular Structure of Three Organic Salts from Benzylamine and Acidic
Components // J Chem Crystallogr (2014) 44: 6–14. Springer Science+Business Media New York 2013.
12. Mo L., Jin S., Zhang W., Guo J., Liu H., Wang D. The crystal structures of ten supramolecular adducts of benzylamine and organic acids //
Journal of Molecular Structure (2020), doi: 10.1016/j.molstruc.2019.127538.
13. Akhmedov K.N., Tadzhimukhamedov Kh.S., Akhmedov U.Ch. Synthesis of N,N-Diethylhydrazine and Its Reactions with Carboxylic
Acids and Alkyl Halides // Russian Journal of General Chemistry, Vol. 75, No. 11, 2005, -P. 1720-1722.
14. Ахмедов У.Ч. N,N-Диэтилгидразиннинг алкилгалогенидлар, карбон кислоталар ва кислота ангидридлари билан реакциялари. –
Тошкент. 2008-йил. Номзодлик диссертацияси.
15. Таджимухамедов Х.С., Ахмедов К.Н., Ахмедов У.Ч. и др. Синтез и строение п-нитробензоата N,N-диэтилгидразиния Узб. хим.
журн. -Ташкент, 2006. -№.1. -C. 24-29.
16. Ахмедов К.Н., Таджимухамедов Х.С., Ахмедов У.Ч. и др. Взаимодействие N,N-диэтилгидразина с муравьиной и о-
бензоилбензойной кислотами Журн. общ. хим. –Cанкт-Петербург, 2007. –Т. 77. –Вып. 8. –С. 1256-1260.
17. Sergei N. Adamovich, Igor A. Ushakov and Alexander V. Vashchenko. Novel guanidinium salts of biologically active (het)
arylchalcogenylacetic acids // Mendeleev Communications, 2017, 27, 88–89. DOI: 10.1016/j.mencom.2017.01.028.
18. Trofimov B.A. et al. Antiviral activity of ammonium of β-alkylthiopropionic acids // Pharmaceutical Chemistry Journal, Vol. 29, No, 1,
pp. 56 - 58, January, 1995.
19. Ellingson B.M., et al. pH-weighted molecular MRI in human traumatic brain injury (TBI) using amine proton chemical exchange
saturation transfer echoplanar imaging (CEST EPI) // NeuroImage: Clinical, 22 (2019) 101736, https://doi.org/10.1016/j.nicl.2019.101736.
20. Qiao Wu, Changling Liu, Jichun Yang, Aiying Guan, Hongjuan Ma. Design, synthesis, and herbicidal activity of novel quaternary
ammonium salt derivatives // Pesticide Biochemistry and Physiology, 143 (2017) 246–251. https://doi.org/10.1016/j.pestbp.2017.05.006.
21. Mirskova A.N., Adamovich S.N., R. G. Mirskov, and M.G. Voronkov. Pharmacologically active salts and ionic liquids based on 2-
hydroxyethylamines, arylchalcogenylacetic acids, and essential metals // Russian Chemical Bulletin, International Edition, Vol. 63, No. 9,
pp. 1869-1883, September, 2014. Springer Science+Business Media, Inc. 2014.
22. Dmitrii Antuganov, Vasilii Timofeev, Ksenija Timofeeva, Yulija Antuganova, and Yulia A. Kondratenko. Evaluation of Protic Ionic
Liquids Based on Triethanolammonium and Tris(hydroxymethyl) methylammonium Salts as Buffers for 68Ga-Radiolabelling of PSMA-
HBED-CC // Medicinal Chemistry & Drug Discovery. ChemistrySelect 2019, 4, 12524-12527. DOI: 10.1002/slct.201902588.
Copyright (c) 2026 «ACTA NUUz»

This work is licensed under a Creative Commons Attribution-NonCommercial-ShareAlike 4.0 International License.




.jpg)

1.png)




