Nucleophilic Addition of Aliphatic Diamines NH2(CH2)nNH2 (n = 6, 9) to Nitrilium Derivatives of the closo-Decaborate Anion [2-B10H9NCR]– (R = CH3, C2H5, nC3H7)

Мұқаба

Дәйексөз келтіру

Толық мәтін

Ашық рұқсат Ашық рұқсат
Рұқсат жабық Рұқсат берілді
Рұқсат жабық Рұқсат ақылы немесе тек жазылушылар үшін

Аннотация

The reaction of a number of nitrilium derivatives of the closo-decaborate anion with hexamethylene- and nonamethylenediamine has been studied. It has been shown that the process proceeds with the functionalization of both amino groups of the nucleophile to form amidines of the type (Bu4N)2[B10H9NH=C(R)NH (CH2)nNH(R)C=NHB10H9] (R = CH3, C2H5, nC3H7; n = 6, 9). Target compounds have been characterized by high resolution multinuclear NMR and ESI mass spectrometry.

Авторлар туралы

V. Voinova

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

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

N. Selivanov

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

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

A. Bykov

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

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

I. Klyukin

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

Email: zhdanov@igic.ras.ru
Россия, 119991, Москва, Ленинский пр-т, 31

A. Zhdanov

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

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

K. Zhizhin

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

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

N. Kuznetsov

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

Хат алмасуға жауапты Автор.
Email: zhdanov@igic.ras.ru
119991, Moscow, Russia

Әдебиет тізімі

  1. 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
  2. Wang L., Sun W., Duttwyler S. et al. // J. Solid State Chem. 2021. V. 299. P. 122167. https://doi.org/10.1016/j.jssc.2021.122167
  3. 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
  4. Deng X., Yao F., Wang Z. et al. // J. Mater. Chem. A. 2023. V. 11. № 2. P. 809. https://doi.org/10.1039/D2TA07827A
  5. Jankowiak A., Baliński A., Harvey J.E. et al. // J. Mater. Chem. C. 2013. V. 1. № 6. P. 1144. https://doi.org/10.1039/c2tc00547f
  6. Korolenko S.E., Zhuravlev K.P., Tsaryuk V.I. et al. // J. Lumin. 2021. V. 237. P. 118156. https://doi.org/10.1016/j.jlumin.2021.118156
  7. Jacob L., Rzeszotarska E., Koyioni M. et al. // Chem. Mater. 2022. V. 34. № 14. P. 6476. https://doi.org/10.1021/acs.chemmater.2c01165
  8. Duchêne L., Remhof A., Hagemann H. et al. // Energy Storage Mater. 2020. V. 25. P. 782. https://doi.org/10.1016/j.ensm.2019.08.032
  9. Toyama N., Kim S., Oguchi H. et al. // J. Energy Chem. 2019. V. 38. P. 84. https://doi.org/10.1016/j.jechem.2019.01.009
  10. Brighi M., Murgia F., Łodziana Z. et al. // J. Power Sources. 2018. V. 404. № August. P. 7. https://doi.org/10.1016/j.jpowsour.2018.09.085
  11. Moury R., Gigante A., Hagemann H. // Int. J. Hydrogen Energy. 2017. V. 42. № 35. P. 22417. https://doi.org/10.1016/j.ijhydene.2017.02.044
  12. Deysher G., Chen Y.-T., Sayahpour B. et al. // ACS Appl. Mater Interfaces. 2022. V. 14. № 42. P. 47706. https://doi.org/10.1021/acsami.2c12759
  13. Evamarie Hey-Hawkins C.V.T. // Boron-Based Compounds: Potential and Emerging Applications in Medicine. John Wiley & Sons Ltd, 2018.
  14. Lin F., Shen Y., Zhang Y. et al. // Chem. Eur. J. 2018. V. 24. № 3. P. 551. https://doi.org/10.1002/chem.201703802
  15. Varkhedkar R., Yang F., Dontha R. et al. // ACS Cent Sci. 2022. V. 8. № 3. P. 322. https://doi.org/10.1021/acscentsci.1c01132
  16. 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
  17. Avdeeva V.V., Garaev T.M., Breslav N.V. et al. // JBIC J. Biol. Inorg. Chem. 2022. https://doi.org/10.1007/s00775-022-01937-4
  18. Ali F., S Hosmane N., Zhu Y. // Molecules. 2020. V. 25. № 4. P. 828. https://doi.org/10.3390/molecules25040828
  19. Barth R.F., Mi P., Yang W. // Cancer Commun. 2018. V. 38. № 1. P. 1. https://doi.org/10.1186/s40880-018-0299-7
  20. 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
  21. Stepanova M., Dobrodumov A., Averianov I. et al. // Polymers (Basel). 2022. V. 14. № 18. P. 3864. https://doi.org/10.3390/polym14183864
  22. Popova T.V., Pyshnaya I.A., Zakharova O.D. et al. // Biomedicines. 2021. V. 9. № 1. P. 74. https://doi.org/10.3390/biomedicines9010074
  23. Mishiro K., Imai S., Ematsu Y. et al. // J. Med. Chem. 2022. V. 65. № 24. P. 16741. https://doi.org/10.1021/acs.jmedchem.2c01586
  24. Zhizhin K.Yu., Zhdanov A.P., Kuznetsov N.T. // Russ. J. Inorg. Chem. 2010. V. 55. № 14. P. 2089. https://doi.org/10.1134/S0036023610140019
  25. Olid D., Núñez R., Viñas C. et al. // Chem. Soc. Rev. 2013. V. 42. № 8. P. 3318. https://doi.org/10.1039/C2CS35441A
  26. Matveev E.Y., Razgonyaeva G.A., Mustyatsa V.N. et al. // Russ. Chem. Bull. 2010. V. 59. № 3. P. 556. https://doi.org/10.1007/s11172-010-0125-0
  27. Zhdanov A.P., Zhdanova K.A., Bykov A.Y. et al. // Polyhedron. 2018. V. 139. P. 125. https://doi.org/10.1016/j.poly.2017.09.050
  28. Neumolotov N.K., Selivanov N.A., Bykov A.Yu. et al. // Russ. J. Inorg. Chem. 2022. V. 67. № 10. P. 1583. https://doi.org/10.1134/S0036023622600861
  29. Naoufal D., Assi Z., Abdelhai E. et al. // Inorg. Chim. Acta. 2012. V. 383. P. 33. https://doi.org/10.1016/j.ica.2011.10.033
  30. Kaszyński P., Ringstrand B. // Angew. Chem. Int. Ed. 2015. V. 54. № 22. P. 6576. https://doi.org/10.1002/anie.201411858
  31. Rzeszotarska E., Novozhilova I., Kaszyński P. // Inorg. Chem. 2017. V. 56. № 22. P. 14351. https://doi.org/10.1021/acs.inorgchem.7b02477
  32. Kapuściński S., Hietsoi O., Pietrzak A. et al. // Chem. Commun. 2022. V. 58. № 6. P. 851. https://doi.org/10.1039/D1CC06485A
  33. Hawthorne M.F., Shelly K., Li F. // Chem. Commun (Camb). 2002. № 6. P. 547. http://www.ncbi.nlm.nih.gov/pubmed/12120120
  34. Avdeeva V.V., Buzin M.I., Dmitrienko A.O. et al. // Chem. Eur. J. 2017. V. 23. № 66. P. 16819. https://doi.org/10.1002/chem.201703285
  35. Naoufal D., Kodeih M., Cornu D. et al. // J. Organomet Chem. 2005. V. 690. № 11. P. 2787. https://doi.org/10.1016/j.jorganchem.2005.01.041
  36. Bondarev O., Sevryugina Y.V., Jalisatgi S.S. et al. // Inorg. Chem. 2012. V. 51. P. 9935.
  37. 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
  38. Matveev E.Yu., Retivov V.M., Razgonyaeva G.A. et al. // Russ. J. Inorg. Chem. 2011. V. 56. № 10. P. 1549. https://doi.org/10.1134/S0036023611100160
  39. Kubasov A.S., Matveev E.Yu., Retivov V.M. et al. // Russ. Chem. Bull. 2014. V. 63. № 1. P. 187. https://doi.org/10.1007/s11172-014-0412-2
  40. Abi-Ghaida F., Laila Z., Ibrahim G. et al. // Dalton Trans. 2014. V. 43. № 34. P. 13087. https://doi.org/10.1039/C4DT00772G
  41. Abi-Ghaida F., Clément S., Safa A. et al. // J. Nanomater. 2015. V. 2015. № 9. P. 1. https://doi.org/10.1155/2015/608432
  42. Wilbur D.S., Thakar M.S., Hamlin D.K. et al. // Bioconjugate Chem. 2009. V. 20. № 10. P. 1983. https://doi.org/10.1021/bc9000799
  43. Li Y., Hamlin D.K., Chyan M.-K. et al. // PLoS One. 2018. V. 13. № 10. P. E0205135. https://doi.org/10.1371/journal.pone.0205135
  44. Klyukin I.N., Selivanov N.A., Bykov A.Y. et al. // Russ. J. Inorg. Chem. 2020. V. 65. № 10. https://doi.org/10.1134/S0036023620100113
  45. Ezhov A.V., Vyal’ba F.Y., Kluykin I.N. et al. // Macroheterocycles. 2017. V. 10. № 4–5. https://doi.org/10.6060/mhc171254z
  46. Daines E.A., Bolotin D.S., Bokach N.A. et al. // Inorg. Chim. Acta. 2018. V. 471. P. 372. https://doi.org/10.1016/j.ica.2017.11.054
  47. Burianova V.K., Bolotin D.S., Mikherdov A.S. et al. // New J. Chem. 2018. V. 42. № 11. P. 8693. https://doi.org/10.1039/c8nj01018h
  48. 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
  49. 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
  50. Voinova V.V., Selivanov N.A., Plyushchenko I.V. et al. // Molecules. 2021. V. 26. № 1. P. 248. https://doi.org/10.3390/molecules26010248
  51. 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
  52. 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

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© В.В. Воинова, Н.А. Селиванов, А.Ю. Быков, И.Н. Клюкин, А.П. Жданов, К.Ю. Жижин, Н.Т. Кузнецов, 2023