The Iminoacylation Reaction of Iodoaniline with [2-B10H9NCCH3]– Anion is a Route to the Preparation of New Boron-Containing Synthons

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This work is devoted to the study of the nucleophilic addition reaction of isomers of iodo-aniline to the nitrile derivative of closo-decaborate anion. The structure of the products was established by multinuclear NMR spectroscopy, ESI-mass spectrometry, and IR spectroscopy. The structure of compound (NBu4)[2-B10H9NHC(CH3)HN(2-C6H4I)] was established by single crystal X-ray analysis.

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Sobre autores

A. Zhdanov

Kurnakov Institute of General and Inorganic Chemistry of the Russian Academy of Sciences

Autor responsável pela correspondência
Email: zhdanov@igic.ras.ru
Rússia, Moscow, 119991

A. Nelyubin

Kurnakov Institute of General and Inorganic Chemistry of the Russian Academy of Sciences

Email: zhdanov@igic.ras.ru
Rússia, Moscow, 119991

N. Selivanov

Kurnakov Institute of General and Inorganic Chemistry of the Russian Academy of Sciences

Email: zhdanov@igic.ras.ru
Rússia, Moscow, 119991

A. Bykov

Kurnakov Institute of General and Inorganic Chemistry of the Russian Academy of Sciences

Email: zhdanov@igic.ras.ru
Rússia, Moscow, 119991

A. Kubasov

Kurnakov Institute of General and Inorganic Chemistry of the Russian Academy of Sciences

Email: zhdanov@igic.ras.ru
Rússia, Moscow, 119991

I. Klyukin

Kurnakov Institute of General and Inorganic Chemistry of the Russian Academy of Sciences

Email: zhdanov@igic.ras.ru
Rússia, Moscow, 119991

K. Zhizhin

Kurnakov Institute of General and Inorganic Chemistry of the Russian Academy of Sciences

Email: zhdanov@igic.ras.ru
Rússia, Moscow, 119991

N. Kuznetsov

Kurnakov Institute of General and Inorganic Chemistry of the Russian Academy of Sciences

Email: zhdanov@igic.ras.ru
Rússia, Moscow, 119991

Bibliografia

  1. Wang Z., Wang Z., Ma X. et al. // Int. J. Hydrogen. Energy. 2021. V. 46. № 60. P. 30750. https://doi.org/10.1016/j.ijhydene.2021.06.196
  2. Wang Z., Liu Y., Zhang H. et al. // J. Colloid. Interface Sci. 2020. V. 566. P. 135. https://doi.org/10.1016/j.jcis.2020.01.047
  3. Duchêne L., Kühnel R.S., Rentsch D. et al. // Chem. Commun. 2017. V. 53. № 30. P. 4195. https://doi.org/10.1039/c7cc00794a
  4. Gigante A., Duchêne L., Moury R. et al. // ChemSusChem. 2019. V. 12. № 21. P. 4832. https://doi.org/10.1002/cssc.201902152
  5. Duchêne L., Lunghammer S., Burankova T. et al. // Chem. Mater. 2019. V. 31. № 9. P. 3449. https://doi.org/10.1021/acs.chemmater.9b00610
  6. Shakirova O.G., Lavrenova L.G., Bogomyakov A.S. et al. // Russ. J. Inorg. Chem. 2015. V. 60. № 7. P. 786. https://doi.org/10.1134/S003602361507013X
  7. Lavrenova L.G., Shakirova O.G. // Russ. J. Inorg. Chem. 2023. V. 68. № 6. P. 690. https://doi.org/10.1134/S0036023623600764
  8. Malinina E.A., Myshletsov I.I., Buzanov G.A. et al. // Molecules. 2023. V. 28. № 1. https://doi.org/10.3390/molecules28010453
  9. Yorov K.E., Zhdanov A.P., Kamilov R.Kh. et al. // ACS Appl. Nano Mater. 2022. V. 5. № 8. P. 11529. https://doi.org/10.1021/acsanm.2c02550
  10. Avdeeva V.V., Garaev T.M., Malinina E.A. et al. // Russ. J. Inorg. Chem. 2022. V. 67. № 1. P. 28. https://doi.org/10.1134/S0036023622010028
  11. Avdeeva V.V., Garaev T.M., Breslav N.V. et al. // J. Biol. Inorg. Chem. 2022. V. 27. P. 421. https://doi.org/10.1007/s00775-022-01937-4
  12. Sun Y., Zhang J., Zhang Y. et al. // Chem. Eur. J. 2018. V. 24. № 41. P. 10364. https://doi.org/10.1002/chem.201801602
  13. Varkhedkar R., Yang F., Dontha R. et al. // ACS Cent. Sci. 2022. V. 8. № 3. P. 322. https://doi.org/10.1021/acscentsci.1c01132
  14. Las’kova Yu.N., Serdyukov A.A., Sivaev I.B. // Russ. J. Inorg. Chem. 2023. V. 68. № 6. P. 621. https://doi.org/10.1134/S0036023623600612
  15. International Atomic Energy Agency, Advances in Boron Neutron Capture Therapy, 2023. https://www.iaea.org/publications/15339/advances-in-boron-neutron-capture-therapy (accessed December 12, 2023).
  16. Igaki H., Murakami N., Nakamura S. et al. // Clin. Transl. Radiat. Oncol. 2022. V. 33. P. 128. https://doi.org/10.1016/j.ctro.2022.02.006
  17. Zhang Z., Chong Y., Liu Y. et al. // Cancers (Basel). 2023. V. 15. № 16. P. 4060. https://doi.org/10.3390/cancers15164060
  18. Stogniy M.Y., Erokhina S.A., Sivaev I.B. et al. // Phosphorus, Sulfur Silicon Relat. Elem. 2019. V. 194. № 10. P. 983. https://doi.org/10.1080/10426507.2019.1631312
  19. Laskova J., Ananiev I., Kosenko I. et al. // Dalton Trans. 2022. V. 51. № 8. P. 3051. https://doi.org/10.1039/D1DT04174F
  20. Prikaznov A.V., Shmal’ko A.V., Sivaev I.B. et al. // Polyhedron. 2011. V. 30. № 9. P. 1494. https://doi.org/10.1016/j.poly.2011.02.055
  21. Nelyubin A.V., Selivanov N.A., Bykov A.Yu. et al. // Int. J. Mol. Sci. 2021. V. 22. № 24. P. 13391. https://doi.org/10.3390/ijms222413391
  22. 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
  23. Kubasov A.S., Turishev E.S., Golubev A.V. et al. // Inorg. Chim. Acta. 2020. V. 507. P. 119589. https://doi.org/10.1016/j.ica.2020.119589
  24. Zhang Y., Sun Y., Wang T. et al. // Molecules. 2018. V. 23. № 12. P. 1. https://doi.org/10.3390/molecules23123137
  25. Feakes D.A., Shelly K., Knobler C.B. et al. // Proc. Natl. Acad. Sci. U.S.A. 2006. V. 91. № 8. P. 3029. https://doi.org/10.1073/pnas.91.8.3029
  26. Bregadze V.I., Sivaev I.B., Dubey R.D. et al. // Chem. Eur. J. 2020. V. 26. № 61. P. 13832. https://doi.org/10.1002/chem.201905083
  27. Kanygin V., Zaboronok A., Taskaeva I. et al. // J. Fluoresc. 2021. V. 31. № 1. P. 73. https://doi.org/10.1007/s10895-020-02637-5
  28. Wang Y., Xu Y., Yang J. et al. // Mater. Chem. Front. 2021. V. 5. № 6. P. 2771. https://doi.org/10.1039/d0qm00867b
  29. Popova Т.V., Pyshnaya I.A., Zakharova O.D. et al. // Biomedicines. 2021. V. 9. № 1. P. 74. https://doi.org/10.3390/biomedicines9010074
  30. Bruker, SAINT, Bruker AXS Inc., Madison, WI, 2018.
  31. Sheldrick G.M. SADABS, Version 2008/1. Bruker AXS Inc., Germany.
  32. Sheldrick G.M. // Acta Crystallogr., Sect. A. 2015. V. 71. № 1. P. 3. https://doi.org/10.1107/S2053273314026370
  33. 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
  34. Voinova V.V., Selivanov N.A., Plyushchenko I.V. et al. // Molecules. 2021. V. 26. № 1. P. 248. https://doi.org/10.3390/molecules26010248
  35. Lavastre O., Cabioch S., Dixneuf P.H. et al. // Tetrahedron. 1997. V. 53. № 22. P. 7595. https://doi.org/10.1016/S0040-4020(97)00451-1
  36. Duval R., Kolb S., Braud E. et al. // J. Comb. Chem. 2009. V. 11. № 6. P. 947. https://doi.org/10.1021/cc900140f
  37. Zhao H., He W., Yao R. et al. // Adv. Synth. Catal. 2014. V. 356. № 14–15. P. 3092. https://doi.org/10.1002/adsc.201400381
  38. da Silva G., Luz A.F.S., Duarte D. et al. // ChemMedChem. 2023. V. 18. № 17. https://doi.org/10.1002/cmdc.202300264
  39. Beladhria A., Beydoun K., Ammar H. et al. // Synthesis (Stuttg.). 2012. V. 44. № 14. P. 2264. https://doi.org/10.1055/s-0031-1291124
  40. Zhdanov A.P., Polyakova I.N., Razgonyaeva G.A. et al. // Russ. J. Inorg. Chem. 2011. V. 56. № 6. https://doi.org/10.1134/S003602361106026X
  41. Zhdanova K.A., Zhdanov A.P., Ezhov A.V. et al. // Russ. Chem. Bull. 2014. V. 63. № 1. P. 194. https://doi.org/10.1007/s11172-014-0413-1
  42. Ezhov A.V., Vyal’ba F.Y., Kluykin I.N. et al. // Macroheterocycles. 2017. V. 10. № 4–5. https://doi.org/10.6060/mhc171254z

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2. Fig. 1. General scheme of the reaction.

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3. Fig. 2. Fragment of 1H NMR spectra of compounds 2 (a), 3 (b), 4 (c).

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4. Fig. 3. Structure of the anion [2-B10H9NH=C(CH3)NH(2-C6H4I)]- based on single crystal PCA data.

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5. Fig. 4. Supramolecular interactions in structure 2.

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