THERMODYNAMIC CHARACTERISTICS OF REVERSED-PHASE CHROMATOGRAPHIC RETENTION OF MORPHOLINIUM 2-((4-(2-METHOXYPHENYL)-5-(PYRIDINYL)-4H-1,2,4-TRIAZOL-3-YL)THIO) ACETATE AND ITS TECHNOLOGICAL IMPURITIES
DOI:
https://doi.org/10.11603/2312-0967.2020.3.11423Keywords:
thermodynamic characteristics, liquid chromatography, 1,2,4-triazole derivativesAbstract
The aim of the work. Thermodynamic description of the morpholinium 2-((4-(2-methoxyphenyl)-5-(pyridinyl)-4H-1,2,4-triazol-3-yl)thio) acetate, pyridin-4-carbohydrazide, 2-isonicotinoyl-N-(2-methoxyphenyl) hydrazin-1-carbothioamide and 4-(2-methoxyphenyl)-5-(pyridinyl)-2,4-dihydro-3H-1,2,4-triazole-3-thion transfer from the mobile phase to the stationary.
Materials and Methods. High performance liquid chromatography system Agilent 1260 Infinity (degasser, binary pump, autosampler, column thermostat, diode array detector, software OpenLAB CDS).
Results and Discussion. The retention factors depending on the change in absolute temperature was determined. The equation of linear dependence is constructed using the least squares method. The value of the standard molar enthalpy of analyte transfer from mobile to stationary phase is calculated. The enthalpies of transfer for most substances are negative, in the process of adsorption on the reversed-phase sorbent occurs with the release of heat and is exothermic.
Conclusions. Standard enthalpies of analytes transfer from mobile phase to stationary phase for morpholinium 2-((4-(2-methoxyphenyl)-5-(pyridinyl)-4H-1,2,4-triazol-3-yl)thio)acetate, pyridine-4-carbohydrazide, 2-isonicotinoyl-N-(2-methoxyphenyl) hydrazine-1-carbothioamide and 4-(2-methoxyphenyl)-5-(pyridinyl)-2,4-dihydro-3H-1,2,4-triazole-3-thione were determined. All compounds, with the exception of pyridine-4-carbohydrazide, have a negative enthalpy of transfer, indicating a predominant transition of these analytes from the mobile phase to the stationary one.
References
Kaplaushenko AG. Synthesis, physicochemical and biological properties of S-derivatives of 5- (2-, 3-, 4-nitrophenyl) -1,2,4-triazole-3-thions. [dissertation]. Kyiv: Kyiv Medical Academy, P. Shupyk National Medical Academy of Postgraduate Education; 2006. Ukrainian.
Kaplaushenko AG. [Methods of synthesis and biological activity of 1,2,4-triazole-3-thions]. Ukr biofarm zhurn. 2009;4(4):48-56. Ukrainian.
Kaplaushenko AG. Synthesis, structure and biological activity of 4-mono- and 4,5-disubstituted 1,2,4-triazole-3-thione derivatives. [dissertation]. Zaporizhzhia: Zaporizhzhia State Medical University; 2012. Ukrainian.
Varynskyi БО, Knysh YeG, Parchenko VV, Panasenko AI, Kaplaushenko AG. [Study of patterns of retention of potential drug substances of a number of 1,2,4-triazol-3-ylthioacetic acids and their salts by HPLC/DMD-MS]. Journal of Organic and Pharmaceutical Chemistry. 2015;13(4):22-33. Ukrainian. DOI: https://doi.org/10.24959/ophcj.15.859
Linford MR, Teutenberg Th, Clark J. Elevated temperatures in liquid chromatography, part I: Benefits and practical considerations. LCGC Europe. 2013;2(26):78-85.
Linford MR, Jensen DS, Teutenberg Th., Clark J. Elevated Temperatures in Liquid Chromatography, Part II: Basic Thermodynamics of Elevated Temperature LC, Including the van 't Hoff Relationship. LCGC North America. 2012;30(11):992-8.
Linford MR, Jensen DS, Teutenberg Th, Clark J. Elevated temperatures in liquid chromatography, part III: A closer look at the van't Hoff equation. LCGC North America. 2012;30(12):1052-7.
Rane VP, Ahirrao VK, Patil KR, Jadhav RA, Ingle RG, More KB et al. Enantiomeric Separation and Thermodynamic investigation of (R)-5-[1-(4-Nitrobenzylsulfonyloxy)-ethyl]-5-(pyridine-2-yl)-[1,3,4]-thiadiazole, a Key Intermediate of Nafithromycin. Analytical Chemistry Letters. 2019;9(5):625-33. doi: 10.1080/22297928.2019.1694433. DOI: https://doi.org/10.1080/22297928.2019.1694433
Zhang L, Hu Yu, Galella E, Tomasella FP, Fish WP. Separation of atropisomers by chiral liquid chromatography and thermodynamic analysis of separation mechanism. Journal of Pharmaceutical Analysis. 2017;7:56-162. doi: 10.1016/j.jpha.2017.03.003. DOI: https://doi.org/10.1016/j.jpha.2017.03.003
Dungelov J, Lehotay J, Krupčik J, Cižmarik J, Armstrong DW. Study of the mechanism of enantioseparation. Part VI: Thermodynamic study of HPLC separation of some enantiomers of phenylcarbamic acid derivatives on a (S,S) Whelk-O 1 column. Journal of Separation Science. 2004; 27(12): 983. Available from: doi: 10.1002/jssc.200301591. DOI: https://doi.org/10.1002/jssc.200301591
Varynskyi B, Kaplaushenko A, Zidan FAl. Development and validation of HPLC-DAD method of determination morpholin-4-ium 2-((4-(2-methoxyphenyl)-5-(pyridin-4-yl)-4H-1,2,4-triazol-3-yl)thio)acetate in a bulk drug. Research Journal of Pharmaceutical, Biological and Chemical Sciences. 2018;9(3): 2200-09.
Varynskyi BO, Kaplaushenko AG. The development and validation of HPLC-DMD method for intermediate products impurities determination of morpholinium 2-((4-(2-methoxyphenyl)-5-(pyridine-4-yl)-4H-1,2,4-triazole-3-yl)thio)acetate in bulk drug. Zaporozhye Medical Journal. 2017;3:373-80. doi:10.14739/2310-1210.2017.3.100947. DOI: https://doi.org/10.14739/2310-1210.2017.3.100947
Downloads
Published
How to Cite
Issue
Section
License
The authors who publish their materials in this journal agree with the following terms:
- Authors reserve the right to authorship of their work and assign to the journal the right to first publish this work under the terms of the Creative Commons Attribution License, which allows other persons to freely distribute the published work with a mandatory reference to the authors of original work and the first publication of work in this journal
. - Authors have the right to make independent extra-exclusive work agreements in the form they are published by this journal (for example, posting work in an electronic repository of an institution or publishing as part of a monograph), provided that the link to the first publication of the work in this journal is maintained.
Journal policy allows and encourages publication of manuscripts on the Internet (for example, in institutions repositories or on personal websites), both before the publication of this manuscript and during its editorial review, as it contributes to productive scientific discussion and positively affects the efficiency and dynamics of the citation of the published work (see The Effect of Open Access).
