Study of Hydrophilic/Hydrophobic Properties of Borylated Iminols [BnHn – 1NHC(OH)R]– (n = 10, 12)

M. N. Ryabchikova; Рябчикова М. Н.; A. V. Nelyubin; Нелюбин А. В.; I. N. Klyukin; Клюкин И. Н.; A. P. Zhdanov; Жданов А. П.; K. Yu. Zhizhin; Жижин К. Ю.; N. T. Kuznetsov; Кузнецов Н. Т.

doi:10.31857/S0044457X23600895

Study of Hydrophilic/Hydrophobic Properties of Borylated Iminols [BnHn – 1NHC(OH)R]– (n = 10, 12)

Authors: Ryabchikova M.N.¹, Nelyubin A.V.², Klyukin I.N.², Zhdanov A.P.², Zhizhin K.Y.², Kuznetsov N.T.²
Affiliations:
1. National Research University Higher School of Economics
2. Kurnakov Institute of General and Inorganic Chemistry, Russian Academy of Sciences
Issue: Vol 68, No 10 (2023)
Pages: 1373-1378
Section: СИНТЕЗ И СВОЙСТВА НЕОРГАНИЧЕСКИХ СОЕДИНЕНИЙ
URL: https://journals.rcsi.science/0044-457X/article/view/140302
DOI: https://doi.org/10.31857/S0044457X23600895
EDN: https://elibrary.ru/EXAKMI
ID: 140302

Cite item

Full Text

Open Access
Restricted Access

Access granted
Restricted Access

Subscription Access

Abstract
About the authors
References
Supplementary files
Statistics

Abstract

The behavior of borylated iminols based on the closo-decaborate and closo-dodecaborate anions in the dichloromethane–water system has been studied as a function of the pH of the aqueous phase. The distribution coefficients of compounds in the n-octanol–water system have been determined: for (Bu4N)[B12H11NHC(OH)CH3], log Kow = –0.46; for (Bu4N)[2-B10H9NHC(OH)CH3], log Kow = –0.51. These compounds show hydrophilic properties similar to those of formic and acetic acids. It has been shown that this method can be used to purify target compounds from hydrolysis products in the preparation of various derivatives as a result of nucleophilic addition of the closo-borate anions to nitrilium derivatives.

Keywords

closo-dodecaborate anion, closo-decaborate anion, nitrilium derivatives, iminols, HPLC

References

Zhang Y., Liu J., Duttwyler S. // Eur. J. Inorg. Chem. 2015. V. 2015. № 31. P. 5158. https://doi.org/10.1002/ejic.201501009
Messina M.S., Axtell J.C., Wang Y. et al. // J. Am. Chem. Soc. 2016. V. 138. № 22. P. 6952. https://doi.org/10.1021/jacs.6b03568
Bolli C., Derendorf J., Jenne C. et al. // Chem. Eur. J. 2014. V. 20. № 42. P. 13783. https://doi.org/10.1002/chem.201403625
Grüner B., Bonnetot B., Mongeot H. // Collect. Czech. Chem. Commun. 1997. V. 62. № 8. P. 1185. https://doi.org/10.1135/cccc19971185
Sivaev I.B., Bregadze V.I., Sjöberg S. // Collect. Czech. Chem. Commun. 2002. V. 67. № 6. P. 679. https://doi.org/10.1135/cccc20020679
Nelyubin A.V., Klyukin I.N., Novikov A.S. et al. // Inorganics. 2022. V. 10. № 11. P. 196. https://doi.org/10.3390/inorganics10110196
Bogdanova E.V., Stogniy M.Yu., Suponitsky K.Yu. et al. // Molecules. 2021. V. 26. № 21. P. 6544. https://doi.org/10.3390/molecules26216544
Laskova J., Ananiev I., Kosenko I. et al. // Dalton Trans. 2022. V. 51. № 8. P. 3051. https://doi.org/10.1039/D1DT04174F
Nelyubin A.V., Selivanov N.A., Bykov A.Yu. et al. // Int. J. Molecular Sci. 2021. V. 22. № 24. P. 13391. https://doi.org/10.3390/ijms222413391
Losytskyy M.Yu., Kovalska V.B., Varzatskii O.A. et al. // J. Lumin. 2016. V. 169. P. 51. https://doi.org/10.1016/j.jlumin.2015.08.042
Kimura S., Masunaga S., Harada T. et al. // Bioorg. Med. Chem. 2011. V. 19. № 5. P. 1721. https://doi.org/10.1016/j.bmc.2011.01.020
Fedotova M.K., Usachev M.N., Bogdanova E.V. et al. // Bioengineering. 2021. V. 9. № 1. P. 5. https://doi.org/10.3390/bioengineering9010005
Zhang Y., Sun Y., Wang T. et al. // Molecules. 2018. V. 23. № 12. P. 1. https://doi.org/10.3390/molecules23123137
Varkhedkar R., Yang F., Dontha R. et al. // ACS Central Sci. 2022. V. 8. № 3. P. 322. https://doi.org/10.1021/acscentsci.1c01132
Sun Y., Zhang J., Zhang Y. et al. // Chem. Eur. J. 2018. V. 24. № 41. P. 10364. https://doi.org/10.1002/chem.201801602
Nelyubin A.V., Sokolov M.S., Selivanov N.A. et al. // Russ. J. Inorg. Chem. 2022. V. 67. № 11. P. 1751. https://doi.org/10.1134/S003602362260109X
Nelyubin A.V., Selivanov N.A., Bykov A.Yu. et al. // Russ. J. Inorg. Chem. 2022. V. 67. № 11. P. 1776. https://doi.org/10.1134/S0036023622601106
Nelyubin A.V., Klyukin I.N., Novikov A.S. et al. // Mendeleev Commun. 2021. V. 31. № 2. P. 201. https://doi.org/10.1016/j.mencom.2021.03.018
Zhdanov A.P., Klyukin I.N., Bykov A.Y. et al. // Polyhedron. 2017. V. 123. P. 176. https://doi.org/10.1016/j.poly.2016.11.035
Nelyubin A.V., Klyukin I.N., Zhdanov A.P. et al. // Russ. J. Inorg. Chem. 2019. V. 64. № 14. P. 1750. https://doi.org/10.1134/S0036023619140043
Šícha V., Plešek J., Kvíčalová M. et al. // Dalton Trans. 2009. № 5. P. 851. https://doi.org/10.1039/B814941K
Stogniy M.Y., Erokhina S.A., Sivaev I.B. et al. // Phosphorus, Sulfur Silicon Relat. Elem. 2019. V. 194. P. 1. https://doi.org/10.1080/10426507.2019.1631312
Guangxian X., Jimei X., Technolgy S. // New Frontiers in Rare Earth Science and Applications. 1985. https://doi.org/10.1016/c2013-0-11730-8
Нелюбин А.В., Клюкин И.Н., Селиванов Н.А. и др. // Журн. неорган. химии. 2023. Т. 68. № 6. С. 768. https://doi.org/10.31857/S0044457X22602310
Yang S.T., White S.A., Hsu S.T. // Ind. Eng. Chem. Res. 1991. V. 30. № 6. P. 1335. https://doi.org/10.1021/ie00054a040
Dupont-Leclercq L., Giroux S., Henry B. et al. // Langmuir. 2007. V. 23. № 21. P. 10463. https://doi.org/10.1021/la7017488
Fu H., Sun Y., Teng H. et al. // Sep. Purif. Technol. 2015. V. 139. P. 36. https://doi.org/10.1016/j.seppur.2014.11.001
Zhdanov A.P., Bykov A.Y., Kubasov A.S. et al. // Russ. J. Inorg. Chem. 2017. V. 62. № 4. P. 468. https://doi.org/10.1134/S0036023617040210
Dearden J.C., Bresnen G.M. // Quantitative Structure-Activity Relationships. 1988. V. 7. № 3. P. 133. https://doi.org/10.1002/qsar.19880070304
Grüner B., Plzák Z. // J. Chromatogr. A. 1997. V. 789. № 1–2. P. 497. https://doi.org/10.1016/S0021-9673(97)00497-4
Horáček O., Papajová-Janetková M., Grüner B. et al. // Talanta. 2021. V. 222. P. 121652. https://doi.org/10.1016/j.talanta.2020.121652