Study of Hydrolysis of Nitrile Derivatives of closo-Dodecaborate Anion (Et4N)[B12H11N≡C–R] (R = Me, Et, nPr, iPr)

A. V. Nelyubin; Нелюбин А. В.; I. N. Klyukin; Клюкин И. Н.; N. A. Selivanov; Селиванов Н. А.; A. Yu. Bykov; Быков А. Ю.; A. S. Kubasov; Кубасов А. С.; A. P. Zhdanov; Жданов А. П.; K. Yu. Zhizhin; Жижин К. Ю.; N. T. Kuznetsov; Кузнецов Н. Т.

doi:10.31857/S0044457X22602310

Study of Hydrolysis of Nitrile Derivatives of closo-Dodecaborate Anion (Et4N)[B12H11N≡C–R] (R = Me, Et, nPr, iPr)

Authors: Nelyubin A.V.¹, Klyukin I.N.¹, Selivanov N.A.¹, Bykov A.Y.¹, Kubasov A.S.¹, Zhdanov A.P.¹, Zhizhin K.Y.¹, Kuznetsov N.T.¹
Affiliations:
1. Kurnakov Institute of General and Inorganic Chemistry, Russian Academy of Sciences
Issue: Vol 68, No 6 (2023)
Pages: 768-773
Section: СИНТЕЗ И СВОЙСТВА НЕОРГАНИЧЕСКИХ СОЕДИНЕНИЙ
URL: https://journals.rcsi.science/0044-457X/article/view/136473
DOI: https://doi.org/10.31857/S0044457X22602310
EDN: https://elibrary.ru/UFEDHV
ID: 136473

Cite item

Full Text

Open Access
Restricted Access

Access granted
Restricted Access

Subscription Access

Abstract
About the authors
References
Supplementary files
Statistics

Abstract

The reaction of nitrile derivatives of closo-dodecaborate anion (Et4N)[B12H11N≡C–R] (R = Me, Et, nPr, iPr) with water has yielded a series of (Et4N)[B12H11NH=C(OH)–R] iminols. It has been demonstrated that the hydrolysis products are in acid–base iminol–amide equilibrium, which can be controlled by changing the pH of a medium. The reaction products have been identified by 11В, 1Н, 13С NMR, IR spectroscopy, and ESI mass spectrometry. The structures of the [B12H11(Z-NH=C(OH)nC3H7)]− and [B12H11(E-NH–C(O)nC3H7)]2− anions have been determined by X-ray single-crystal diffraction.

Keywords

closo-dodecaborates, nitrile derivatives, iminols, amides

References

Geis V., Guttsche K., Knapp C. et al. // Dalton Trans. 2009. № 15. P. 2687. https://doi.org/10.1039/b821030f
Bolli C., Derendorf J., Jenne C. et al. // Chem. A Eur. J. 2014. V. 20. № 42. P. 13783. https://doi.org/10.1002/chem.201403625
Bolli C., Derendorf J., Jenne C. et al. // Eur. J. Inorg. Chem. 2017. V. 2017. № 38–39. P. 4552. https://doi.org/10.1002/ejic.201700620
Zhang Y., Liu J., Duttwyler S. // Eur. J. Inorg. Chem. 2015. V. 2015. № 31. P. 5158. https://doi.org/10.1002/ejic.201501009
Kirchmann M., Wesemann L. // Dalton Trans. 2008. № 4. P. 444. https://doi.org/10.1039/B715305H
Matveev E.Y., Avdeeva V.V., Zhizhin K.Y. et al. // Inorganics. 2022. V. 10. № 12. P. 238. https://doi.org/10.3390/inorganics10120238
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
Gigante A., Duchêne L., Moury R. et al. // ChemSusChem. 2019. V. 12. № 21. P. 4832. https://doi.org/10.1002/cssc.201902152
Duchêne L., Lunghammer S., Burankova T. et al. // Chem. Mater. 2019. V. 31. № 9. P. 3449. https://doi.org/10.1021/acs.chemmater.9b00610
Derdziuk J., Malinowski P.J., Jaroń T. // Int. J. Hydrogen Energy. 2019. V. 44. № 49. P. 27030. https://doi.org/10.1016/j.ijhydene.2019.08.158
Rao M.H., Muralidharan K. // Polyhedron. 2016. V. 115. P. 105. https://doi.org/10.1016/j.poly.2016.03.062
Hagemann H. // Molecules. 2021. V. 26. № 24. P. 7425. https://doi.org/10.3390/molecules26247425
Sharon P., Afri M., Mitlin S. et al. // Polyhedron. 2019. V. 157. P. 71. https://doi.org/10.1016/j.poly.2018.09.055
Zhilitskaya L.V., Shainyan B.A., Yarosh N.O. // Molecules. 2021. V. 26. № 8. P. 2190. https://doi.org/10.3390/molecules26082190
Barth R.F., Zhang Z., Liu T. // Cancer. Commun. 2018. V. 38. № 1. P. 36. https://doi.org/10.1186/s40880-018-0280-5
Hattori Y., Kusaka S., Mukumoto M. et al. // J. Med. Chem. 2012. V. 55. № 15. P. 6980. https://doi.org/10.1021/jm300749q
Hatanaka H. // J. Neurol. 1975. V. 209. № 2. P. 81. https://doi.org/10.1007/BF00314601
Wiersema R.J., Middaugh R.L. // Inorg. Chem. 1969. V. 8. № 10. P. 2074. https://doi.org/10.1021/ic50080a009
Guangxian X., Jimei X., Technology S. New Frontiers in Rare Earth Science and Applications. 1985. https://doi.org/10.1016/c2013-0-11730-8
Varkhedkar R., Yang F., Dontha R. et al. // ACS Cent. Sci. 2022. V. 8. № 3. P. 322. https://doi.org/10.1021/acscentsci.1c01132
Sun Y., Zhang J., Zhang Y. et al. // Chem. A Eur. J. 2018. V. 24. № 41. P. 10364. https://doi.org/10.1002/chem.201801602
Krause L., Herbst-Irmer R., Sheldrick G.M. et al. // J. Appl. Crystallogr. 2015. V. 48. № 1. P. 3. https://doi.org/10.1107/S1600576714022985
Sheldrick G.M. // Acta Crystallogr., Sect. C: Struct. Chem. 2015. V. 71. № 1. P. 3. https://doi.org/10.1107/S2053229614024218
Dolomanov O.V., Bourhis L.J., Gildea R.J. et al. // J. Appl. Crystallogr. 2009. V. 42. № 2. P. 339. https://doi.org/10.1107/S0021889808042726
Nelyubin A.V., Selivanov N.A., Bykov A.Y. et al. // Int. J. Mol. Sci. 2021. V. 22. № 24. P. 13391. https://doi.org/10.3390/ijms222413391
Nelyubin A.V., Klyukin I.N., Novikov A.S. et al. // Inorganics. 2022. V. 10. № 11. P. 196. https://doi.org/10.3390/inorganics10110196
Нелюбин А.В., Соколов М.С., Селиванов Н.А. и др. // Журн. неорган. химии. 2022. Т. 67. С. 1562.
Нелюбин А.В., Селиванов Н.А., Клюкин И.Н. и др. // Журн. неорган. химии. 2021. Т. 66. С. 1297.
Zhang Y., Sun Y., Wang T. et al. // Molecules. 2018. V. 23. № 12. P. 1. https://doi.org/10.3390/molecules23123137
Bogdanova E.V., Stogniy M.Y., Suponitsky K.Y. 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