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://rjonco.com/0044-457X/article/view/665241
DOI: https://doi.org/10.31857/S0044457X22602310
EDN: https://elibrary.ru/UFEDHV
ID: 665241

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Abstract
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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