Effect of solvent H/D isotope substitution and temperature on some thermodynamic properties of tetramethylenediethylentetramine (pharmaceutical theotropin) in aqueous solutions

Evgeny Ivanov; Elena Lebedeva; Nadezhda Ivanova; Vladimir Baranov; Angelina Kravchenko

doi:10.52957/27821900_2023_01_08

UDC 544.35.038 UDC 544.353.2 UDC 544.582.6 UDC 546.212.027

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EFFECT OF SOLVENT H/D ISOTOPE SUBSTITUTION AND TEMPERATURE ON SOME THERMODYNAMIC PROPERTIES OF TETRAMETHYLENEDIETHYLENTETRAMINE (PHARMACEUTICAL THEOTROPIN) IN AQUEOUS SOLUTIONS Effect of solvent H/D isotope substitution and temperature on some thermodynamic properties of tetramethylenediethylentetramine (pharmaceutical theotropin) in aqueous solutions

АА Аа

Published in From Chemistry Towards Technology Step-By-Step · Volume 4, Issue 1 · Pages 8–24 · Rubric: Scientific articles

DOI: https://doi.org/10.52957/27821900_2023_01_08

Received: 13.02.2023 Accepted: 21.03.2023 Published: 23.03.2023

Authors

Evgeny Ivanov

Elena Lebedeva

Nadezhda Ivanova

Vladimir Baranov

et al.

Angelina Kravchenko

Evgeny Ivanov

Academic degree: candidate of chemical sciences

Institute of Solution Chemistry of G.A. Krestov of the Russian Academy of Sciences Senior Researcher · Ivanovo

Elena Lebedeva

Academic degree: candidate of chemical sciences

Institute of Solution Chemistry of G.A. Krestov of the Russian Academy of Sciences Researcher · Ivanovo

Nadezhda Ivanova

Academic degree: candidate of chemical sciences

Science rang: docent

Ivanovo Power Engineering Institute Ivanovo

Vladimir Baranov

Academic degree: candidate of chemical sciences

N.D. Zelinsky Institute of Organic Chemistry of the Russian Academy of Sciences Researcher · Russian Federation · Moscow

Angelina Kravchenko

Academic degree: doctor of chemical sciences

Science rang: professor

N.D. Zelinsky Institute of Organic Chemistry of the Russian Academy of Sciences Leading Researcher · Russian Federation · Moscow

ABSTRACT

Pri temperaturah 278,15 K, 288,15 K, 298,15 K, 308,15 K i 318,15 K i atmosfer-nom davlenii r = 0,1 MPa izmereny plotnosti rastvorov farmacevticheskogo sredstva «teotropin» ili tetrametilendietilentetramin (TMDETA) v tyazheloy vode (D2O) v intervale soderzhaniy rastvorennogo veschestva v shkale molyal'nosti ot 0,01 do 0,12 mol'∙(kg rastvoritelya) 1. Pogreshnost' izmereniya plotnosti s pomosch'yu densimetra Anton Paar DMA 5000 M (osnaschennogo koleblyuscheysya U-obraznoy trubkoy) sostavlyala ne bolee 0,03 kg·m-3. Opredeleny standartnye (pri beskonechnom razbavlenii) molyarnye ob'emy i izobarnye rasshiryaemosti TMDETA kak rastvorennogo v D2O veschestva, a takzhe sootvetstvuyuschie D2O–H2O izotopnye effekty rastvoritelya (IE). Poslednie byli rasschitany s ispol'zovaniem ranee poluchennyh dannyh po ob'emnym svoystvam sistemy (H2O + TMDETA). Ustanovleno, chto neznachitel'nye po velichine IE v standartnom molyarnom ob'eme TMDETA vozrastayut s povysheniem temperatury. Na osnovanii analiza vkladov v standartnyy molyarnyy ob'em TMDETA v ramkah teorii masshtabnyh chastic (TMCh) podtverzhdeno, chto molekula etogo rastvorennogo veschestva vzaimodeystvuet s vodoy (osobenno v srede D2O) sil'nee, chem menee razvetvlennaya molekula geksametilentetramina (GMTA) ili farmakologicheski aktivnogo «urotropina», yavlyayuschegosya rodstvennym soedineniem aminal'nogo (kletkopodobnogo) stroeniya. Sovmestnoe obsuzhdenie ob'emno- i ental'piyno-izotopnyh harakteristik processa gidratacii TMDETA (i GMTA) v ramkah TMCh privelo k vyvodu o tom, chto strukturnaya matrica D2O dolzhna luchshe podhodit' dlya vklyucheniya v nee bolee «ob'emistoy» molekuly TMDETA.

KEYWORDS

teotropin; standartnye ob'em i rasshiryaemost'; standartnaya ental'piya rastvoreniya; obychnaya i tyazhelaya voda; H/D izotopnyy effekt rastvoritelya

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1. Zwier J.M., Brouwer A.M., Buma W.J., Troisi A., Zerbetto F. Structure and photophysics of an old, new molecule: 1,3,6,8-tetraazatricyclo[4.4.1.1(3,8)]dodecane // J. Am. Chem. Soc. 2002. Vol. 124. R. 149-158. DOI:https://doi.org/10.1021/ja016971b.

2. Ivanov E.V. Temperature-dependent standard volumetric properties of hexamethylenetetramine in ordinary and deuterated water: A study resolving debatable issues being commented in the [Journal of Molecular Liquids, 248 (2017) 48-52] // J. Mol. Liq. 2018. Vol. 272. R. 218-225. DOI:https://doi.org/10.1016/j.molliq.2018.09.046.

3. Vasil'ev D.A., Hayrullin I.N., Zolotuhin S.N., Feoktistova N.A., Kur'yanova N.H. Izuchenie baktericidnogo i bakteriostaticheskogo deystviya teotropina na mikroorganizmy razlichnoy morfologicheskoy struktury // Vestnik Ul'yanovskoy gos. sel'skohoz. akademii. 2011. T. 1, vyp. 13. S. 75-78.

4. Balysheva V.I., Nesterov E.A., Lunicin A.V., Zhivoderov S.P., Gorshkova T.F., Lapteva O.G., Balyshev V.M., Kolbasov D.V. Effektivnost' trehvalentnoy inaktivirovannoy vakciny protiv kataral'noy lihoradki krupnogo rogatogo skota i melkih zhvachnyh zhivotnyh // Doklady Ros. akad. sel'skohoz. nauk. 2013. T. 39, vyp 4. S. 49-51.

5. Blanco L.H., Dávila M.T. Osmotic and activity coefficients of two macrocyclic aminals in aqueous solution at 288.15, 293.15, 298.15 and 303.15 K // Fluid Phase Equil. 2010. Vol. 293. R. 237-241. DOI:https://doi.org/10.1016/j.fluid.2010.03.012.

6. Romero C.M., Mesa H.J. Effect of temperature on the partial molar volumes and viscosities of two macrocyclic aminals in water and deuterium oxide // J. Mol. Liq. 2017. Vol. 242. R. 244-248. DOI:https://doi.org/10.1016/j.molliq.2017.06.101.

7. Ivanov E.V., Batov D.V., LebedevaE.Yu., Baranov V.V. Some interaction-related thermodynamic properties of aqueous tetramethylenediethylenetetramine (drug teotropine) solutions: Effect of the solvent H/D isotope substitution and temperature // J. Mol. Liq. 2021. Vol. 326. R. 115274/1-115274/8. DOI:https://doi.org/10.1016/j.molliq.2020.115274.

8. Blanco L.H., Sanabria N.R. Solubility of 1,3,6,8-tetraazatricyclo[4.4.1.13,8]dodecane (TATD) in water at temperatures between 275 K and 303 K // J. Chem. Eng. Data. 2007. Vol. 52. R. 2288-2290. DOI:https://doi.org/10.1021/je700304z.

9. Salamanca Y.P., Blanco L.H., Vargas E.F. Enthalpies of solution of 1,3,6,8-tetraazatricyclo[4.4.1.13,8]dodecane in aqueous solution as a function of concentration and temperature // J. Therm. Anal. Calorim.2013. Vol. 114. R. 451-455. DOI:https://doi.org/10.1007/s10973-012-2870-9.

10. Ivanov E.V., Batov D.V. Unusual behavior of temperature-dependent solvent H/D isotope effects in the enthalpy and heat capacity of hexamethylenetetramine (urotropine) hydration // J. Mol. Liq. 2019. Vol. 285. R. 508-514. DOI:https://doi.org/10.1016/j.molliq.2019.04.104.

11. Soper A.K., Benmore C.J. Quantum differences between heavy and light water // Phys. Rev. Lett. 2008. Vol. 101. 065502/1-065502/4. DOI:https://doi.org/10.1103/PhysRevLett.101.065502.

12. Ivanov E.V. Some comments on the paper “Effect of temperature on the partial molar volumes and viscosities of two macrocyclic aminals in water and deuterium oxide” by Carmen M. Romero and Holman J. Mesa [Journal of Molecular Liquids, 242 (2017) 244-248] // J. Mol. Liq. 2017. Vol. 248. R. 48-52. DOI:https://doi.org/10.1016/j.molliq.2017.09.125 (and references therein).

13. Ivanov E.V., Lebedeva E.Y., Baranov V.V., Kravchenko A.N. Volume properties of tetramethylenediethylene-tetramine (pharmaceutical teotropine) in aqueous solutions between 278.15 and 318.15 K // J. Mol. Liq. 2022. Vol. 174. R. 106-860/1-106860/6. DOI:https://doi.org/10.1016/j.jct.2022.106860.

14. Ansari M.S., Hafiz-ur-Rehman. Aquamolality: a useful concentration unit // Phys. Chem. Liq.: Int. J. 2011. Vol. 49. R. 743-745. DOI:https://doi.org/10.1080/00319104.2010.509723.

15. Abrosimov V.K., Ivanov E.V. Densimetriya rastvorov // Teoreticheskie i eksperimental'nye metody himii rastvorov. M.: Prospekt, 2011. S. 425-463.

16. Ivanov E.V. Ponyatie sol'vomolyal'nosti kak etap v razvitii predstavleniy o strukturno-termodinamicheskih harakteristikah rastvorov: k yubileynym datam so dnya rozhdeniya G.A. Krestova i sozdaniya nosyaschego ego imya Instituta himii rastvorov RAN // Izv. vuzov. Himiya i him. tehnologiya. 2021. T.1, vyp. 64. S. 6-15. DOI:https://doi.org/10.6060/ivkkt.20216410.6461 (and references therein).

17. Wüzburger S., Sartorio R., Guarino G., Nisi M. Volumetric properties of aqueous solutions of polyols between 0.5 and 25 °C // J. Chem. Soc., Faraday Trans. 1. 1988. Vol. 84. R. 2279-2287. DOI:https://doi.org/10.1039/F19888402279.

18. Ivanov E.V., Lebedeva E.Yu., Petrovskaya S.G., Baranov V.V., Kravchenko A.N., Ivanova N.G. Volume-related interaction parameters for dilute solutions of Mebicaret (2,4-dimethyl-6,8-diethylglycoluril) in normal and heavy water between 278.15 K and 318.15 K // J. Mol. Liq. 2017. Vol. 242. R. 160-167. DOI:https://doi.org/10.1016/j.molliq.2017.07.003(and references therein).

19. Mak T.C.W. Hexamethylenetetramine hexahydrate: a new type of clathrate hydrate // J. Chem. Phys. 1965. Vol. 43. R. 2799-2805. DOI:https://doi.org/10.1063/1.1697212.

20. Kell G.S. Effect of isotopic composition, temperature, pressure, and dissolved gases on the density of liquid water // J. Phys. Chem. Ref. Data. 1977. Vol. 6, rr. 1109-1131. DOI:https://doi.org/10.1063/1.555561.

21. Lepori L., Gianni P. Partial molar volumes of ionic and nonionic organic solvents in water: a simple additivity scheme based on the intrinsic volume approach // J. Solution Chem. 2000. Vol. 29. R. 405-447. DOI:https://doi.org/10.1023/A:1005150616038.

22. Kuz'min V.S., Kacer S.B. Metod rascheta van-der-vaal'sovskih ob'emov organicheskih molekul // Izv. RAN. Ser. him. 1992. № 4. S. 922-931.

23. Hepler L.G. Thermal expansion and structure in water and aqueous solutions // Can. J. Chem. 1969. Vol. 47. R. 4613-4617. DOI:https://doi.org/10.1139/v69-762.

24. Pierotti R.A. A scaled particle theory of aqueous and nonaqueous solutions // Chem. Rev. 1976. Vol. 76. R. 717 726. DOI:https://doi.org/10.1021/cr60304a002.

25. Ivanov E.V. Thermodynamic interrelation between excess limiting partial molar characteristics of a liquid nonelectrolyte // J. Chem. Thermodyn.2012. Vol. 47. R. 437-440. DOI:https://doi.org/10.1016/j.jct.2011.11.018.

26. Malenkov G.G., Toryanik A.I. Issledovanie molekulyarnoy struktury vodnyh rastvorov geksametilentetramina // Zhurn. strukt. himii. 1976. T. 17, vyp. 1. S. 58-62.

27. Kuznecov A.I., Shukkur A.H., Kamara K. Sintez 4,5-digidro-1,6:3,8-dimetano-1,3,6,8-benzotetrazecina // Izv. RAN. Ser. himicheskaya. 2008. № 7. S. 1544-1546.

28. Peori M.B., Vaughan K., Hooper D. Synthesis and characterization of novel bis-triazenes: 3,8-di[2-aryl-1-azenyl]-1,3,6,8-tetraazabicyclo[4.4.1]undecanes and 1,3-di-2-[(4-methoxyphenyl)-1-diazenyl]imidazolidine. The reaction of diazonium ions with ethylenediamine/formaldehyde mixtures // J. Org. Chem. 1998. Vol. 63. R. 7437-7444. DOI:https://doi.org/10.1021/jo981276g.

29. Clavijo J.A., Blanco L.H. Effect of two macrocyclic aminals on the temperature of maximum density of water // J. Solution Chem. 2012. Vol. 41. R. 680-689. DOI:https://doi.org/10.1007/s10953-011-9736-9.

30. Wagner Z., Bendová M., Rotrekl J., Sýkorová A., Čanji M., Parmar N. Density and sound velocity measurement by an Anton Paar DSA 5000 density meter: Precision and long-time stability // J. Mol. Liq. 2021. Vol. 329. 155547/-155547/17. DOIhttps://doi.org/10.1016/j.molliq.2021.115547.

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Ivanov E. V., Lebedeva E. Y., Ivanova N. G., Baranov V. V., Kravchenko A. N. Effect of solvent H/D isotope substitution and temperature on some thermodynamic properties of tetramethylenediethylentetramine (pharmaceutical theotropin) in aqueous solutions // From Chemistry Towards Technology Step-By-Step. 2024. no. 1. pp. 8-24. DOI: https://doi.org/10.52957/27821900_2023_01_08. (Date of access 24.09.2026).

MLA

Evgeny Ivanov, Lebedeva E. Y., Ivanova N. G., Baranov V. V., Kravchenko A. N.. "Effect of solvent H/D isotope substitution and temperature on some thermodynamic properties of tetramethylenediethylentetramine (pharmaceutical theotropin) in aqueous solutions." From Chemistry Towards Technology Step-By-Step 4.1 (2024): 8-24. DOI: https://doi.org/10.52957/27821900_2023_01_08.

APA

Ivanov E. V., Lebedeva E. Y., Ivanova N. G., Baranov V. V., Kravchenko A. N. (2024). Effect of solvent H/D isotope substitution and temperature on some thermodynamic properties of tetramethylenediethylentetramine (pharmaceutical theotropin) in aqueous solutions. From Chemistry Towards Technology Step-By-Step, 4(1), 8-24. https://doi.org/10.52957/27821900_2023_01_08

Chicago

Evgeny Ivanov, Lebedeva E. Y., Ivanova N. G., Baranov V. V., Kravchenko A. N.. "Effect of solvent H/D isotope substitution and temperature on some thermodynamic properties of tetramethylenediethylentetramine (pharmaceutical theotropin) in aqueous solutions." From Chemistry Towards Technology Step-By-Step 4, no. 1 (2024): 8-24. https://doi.org/10.52957/27821900_2023_01_08.

WIKI

{{cite journal | author = Ivanov E. V., Lebedeva E. Y., Ivanova N. G., Baranov V. V., Kravchenko A. N. | title = Effect of solvent H/D isotope substitution and temperature on some thermodynamic properties of tetramethylenediethylentetramine (pharmaceutical theotropin) in aqueous solutions | journal = From Chemistry Towards Technology Step-By-Step | year = 2024 | volume = 4 | issue = 1 | pages = 8-24 | doi = 10.52957/27821900_2023_01_08 }}

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