Redox-Active Tin(IV) Complexes Based on Sterically Hindered Catecholate Ligands

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Abstract

The oxidative addition of sterically hindered 3,6-dicyclohexyl-o-benzoquinone (L1), 3,5-di-tert-octyl-o-benzoquinone (L2), 4-tert-octyl-o-benzoquinone (L3), and 3,5-bis(2-phenylpropyl)-o-benzoqui-none (L4) to tin(II) chloride in THF affords the corresponding tin(IV) catecholate complexes with the generalformula RCatSnCl2 · 2THF, where Cat is the catecholate fragment; and R is 3,6-с-Hex (I), 3,5-tert-Oct (II), 4-tert-Oct (III), and 3,5-C(Me)2 Ph (IV), regardless of the molar ratio of the starting reactants. The molecu-lar structures of substituted o-benzoquinone L4 and complexes I and III in the crystalline form are determined by X-ray diffraction (XRD) (CIF files CCDC nos. 2259370 (L4), 2259371 (I), and 2259372 (III)). The oxidation-reduction properties of synthesized compounds I–IV are studied by cyclic voltammetry.

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About the authors

S. V. Baryshnikova

Razuvaev Institute of Organometallic Chemistry, Russian Academy of Sciences

Author for correspondence.
Email: baryshnikova@iomc.ras.ru
Russian Federation, Nizhny Novgorod

M. V. Arsen’eva

Razuvaev Institute of Organometallic Chemistry, Russian Academy of Sciences

Email: baryshnikova@iomc.ras.ru
Russian Federation, Nizhny Novgorod

N. O. Druzhkov

Razuvaev Institute of Organometallic Chemistry, Russian Academy of Sciences

Email: baryshnikova@iomc.ras.ru
Russian Federation, Nizhny Novgorod

G. K. Fukin

Razuvaev Institute of Organometallic Chemistry, Russian Academy of Sciences

Email: baryshnikova@iomc.ras.ru
Russian Federation, Nizhny Novgorod

E. V. Baranov

Razuvaev Institute of Organometallic Chemistry, Russian Academy of Sciences

Email: baryshnikova@iomc.ras.ru
Russian Federation, Nizhny Novgorod

A. V. Piskunov

Razuvaev Institute of Organometallic Chemistry, Russian Academy of Sciences

Email: baryshnikova@iomc.ras.ru
Russian Federation, Nizhny Novgorod

References

  1. Pierpont C. // Coord. Chem. Rev. 2001. V. 219–221. P. 415.
  2. Kaim W.// Inorg. Chem. 2011. V. 50. P. 9752.
  3. Mao G., Song Y., Hao T. et al. // Chin. Sci. Bull. 2014. V. 59. P. 2936.
  4. Starikova A.A., Minkin V. I. // Russ. Chem. Rev. 2018. V. 87. P. 1049.
  5. Fomenko I.S., Gushchin A. L. // Russ. Chem. Rev. 2020. V. 89. P. 966.
  6. Broere D.L., Plessius R., Van der Vlugt J. I. // Chem. Soc. Rev. 2015. V. 44. P. 6886.
  7. Luca O.R., Crabtree R. H. // Chem. Soc. Rev. 2013. V. 42. P. 1440.
  8. Baryshnikova S.V., Poddel’sky A.I. // Molecules. 2022. V. 27. P. 3928.
  9. Ershova I.V., Piskunov A. V., and Cherkasov V. K. // Russ. Chem. Rev. 2020. V. 89. P. 1157.
  10. Pashanova K.I., Poddel’sky A.I., Piskunov A. V. // Coord. Chem. Rev. 2022. V. 459. P. 214399.
  11. Zanello P., Corsini M. // Coord. Chem. Rev. 2006. V. 250. P. 2000.
  12. Poddel’skii A.I., Abakumov G. A., Bubnov M. P., Cherkasov V. K., and Abakumova L. G. // Izv. Akad. Nauk. Ser. Khim. 2004. № 6. P. 1142.
  13. Abakumov G.A., and Nevodchikov V. I. // Dokl. Akad. Nauk SSSR. 1982. V. 266. № 6. P. 1407.
  14. Lange C.W., Foldeaki M., Nevodchikov V. I. et al. // J. Am. Chem. Soc. 1992. V. 114. P. 4220.
  15. Jung O.-S., Pierpont C. G. // J. Am. Chem. Soc. 1994. V. 116. P. 2229.
  16. Nevodchikov V.I., Abakumov G. A., Cherkasov V. K., Razuvaev G. A. // J. Organomet. Chem. 1981. V. 214. P. 119.
  17. Pierpont C.G., Buchanan R. M. // Coord. Chem. Rev. 1981. V. 38. P. 45.
  18. Poddel’sky A.I., Cherkasov V. K., Abakumov G. A. // Coord. Chem. Rev. 2009. V. 253. P. 291.
  19. Abakumov G.A., Poddel’sky A.I., Grunova E. V. et al. // Angew. Chem. 2005. V. 117. P. 2827.
  20. Cherkasov V. K. Abakumov G. A., Grunova E. V. et al. // Chem. Eur. J. 2006. V. 12. P. 3916.
  21. Piskunov A.V., Ershova I. V., Fukin G. K., Shavyrin A. S. // Inorg. Chem. Commun. 2013. V. 38. № 12. P. 127.
  22. Piskunov A.V., Piskunova M. S., and Chegerev M. G. // Russ. Chem. Bull. 2014. № 4. P. 912.
  23. Fedushkin I.L., Dodonov V. A., Skatova A. A. et al. // Chem. Eur. J. 2018. V. 24. № 8. P. 1877.
  24. Fedushkin I.L., Nikipelov A. S., Morozov A. G. et al. // Chem. Eur. J. 2012. V. 18. P. 255.
  25. Ilyakina E.V., Poddel’sky A.I., Cherkasov V. K., Abakumov G.A. // Mendeleev Commun. 2012. V. 22. P. 208.
  26. Ilyakina E.V., Poddel’sky A.I., Piskunov A.V. et al. // Inorg. Chim. Acta. 2013. V. 394. P. 282.
  27. Gordon A., and Ford R. The Chemist’s Companion: A Handbook of Practical Data, Techniques, and References. New York: Wiley, 1972.
  28. Райхардт К. Растворители и эффекты среды в органической химии. М.: Мир, 1991. 763 с.
  29. Kocherova T.N., Druzhkov N. O., Mart’yanov K.A. et al. // Russ. Chem. Bull. 2020. V. 69. № 12. P. 2383.
  30. Kocherova T.N., Druzhkov N. O., Arsen’ev M.V. et al. // Russ. Chem. Bull. 2023. V. 72. № 5. P. 1192.
  31. Data Collection, Reduction and Correction Program. CrysAlisPro 1.171.38.46 – Software Package. Rigaku OD, 2015.
  32. APEX4. Bruker Molecular Analysis Research Tool. Version 2021.4–0. Madison (WI, USA): Bruker AXS Inc., 2021.
  33. SAINT Data Reduction and Correction Program. Version 8.40B. Madison (WI, USA): Bruker AXS, 2019.
  34. Krause L., Herbst-Irmer R., Sheldrick G. M., Stalke D. // J. Appl. Cryst. 2015. V. 48. P. 3.
  35. Sheldrick G. // Acta Crystallogr. A. 2015. V. 71. P. 3.
  36. Sheldrick G.M. // SHELXTL. Version 6.14. Structure Determination Software Suite; Madison (WI, USA): Bruker AXS, 2003.
  37. Sheldrick G. // Acta Crystallogr. C. 2015. V. 71. P. 3.
  38. SCALE3 ABSPACK: Empirical absorption correction. CrysAlisPro 1.171.38.46 – Software Package, Rigaku OD, 2015.
  39. SADABS. Version 2016/2. Bruker/Siemens Area Detector Absorption Correction Program. Madison (WI, USA): Bruker AXS., 2016.
  40. Becke A.D. // J. Chem. Phys. 1993. V. 98. P. 5648.
  41. Lee C., Yang W., Parr R. G. // Phys. Rev. B. 1988. V. 37. P. 785.
  42. Dovesi R., Erba A., Orlando R. et al. // WIREs Comput Mol Sci. 2018. V. 8. P. 1360.
  43. Godbout N., Salahub D. R., Andzelm J., Wimmer E. // Can. J. Chem. 1992. V. 70. P. 560.
  44. Pritchard B.P., Altarawy D. et al. // J. Chem. Inf. Model. 2019. V. 59. P. 4814.
  45. Feller D. // J. Comput. Chem. 1996. V. 17. P. 1571.
  46. Schuchardt K.L., Didier B. T., Elsethagen T. et al. // J. Chem. Inf. Model. 2007. V. 47. № 3. P. 1045.
  47. Spek A.L. // Acta Crystallogr. C. 2015. V. 71. P. 9.
  48. Jelsch C., Guillot B., Lagoutte A., Lecomte C. // J. Appl. Crystallogr. 2005. V. 38. P. 38.
  49. Hansen N.K., Coppens P. // Acta Crystallogr. A. 1978. V. 34. P. 909.
  50. Stash A.I., Tsirelson V. G. // J. Appl. Cryst. 2014. V. 47. P. 2086.
  51. Batsanov S. // Russ. J. Inorg. Chem. 1991. V. 36. P. 1694.
  52. Baryshnikova S.V., Poddel’sky A.I., Bellan E. V. et al. // Inorg. Chem. 2020. V. 59. P. 6774.
  53. Lado A.V., Poddel’sky A.I., Piskunov A. V. et al. // Inorg. Chim. Acta. 2005. V. 358. P. 4443.
  54. Piskunov A.V., Lado A. V., Ilyakina E. V. et al. // J. Organomet. Chem. 2008. V. 693. P. 128.
  55. Turek J., Kampová H., Padelkova Z., Ruzicka A. // J. Organomet. Chem. 2013. V. 745–746. P. 25.
  56. Annan T.A., McGarvey B.R., Ozarowski A. et al. // Dalton Trans. 1989. V. 3. P. 439.
  57. Zubieta J.A., Zuckerman J. J. // Prog. Inorg. Chem. New York: Wiley Interscience, 1978. V. 24. P. 251.
  58. Archer S.J., Koch K. R., Schmidt S. // Inorg. Chim. Acta. 1987. V. 126. P. 209.
  59. Baryshnikova S.V., Bellan E. V., Poddel’sky A.I. et al. // Eur. J. Inorg. Chem. 2016. № 33. P. 5230.
  60. Ilyakina E.V., Poddel’sky A.I., Fukin G. K. et al. // Inorg. Chem. 2013. V. 52. P. 5284.
  61. Brown S.N. // Inorg. Chem. 2012. V. 51. С. 1251.
  62. Fukin G.K., Cherkasov A. V. // Mendeleev Commun. 2021. V. 31. P. 182.
  63. Pochekutova T.S., Fukin G. K., Baranov E. V. et al. // Inorg. Chim. Acta. 2022. V. 531. P. 120734.
  64. Bader R.F.W. Atoms in Molecules – A Quantum Theory. Oxford: Oxford Univ. Press., 1990.
  65. Fukin G.K., Baranov E. V., Jelsch C. et al. // J. Phys. Chem. A. 2011. V. 115. P. 8271.
  66. Фукин Г.К., Самсонов М. А., Баранов Е. В. и др. // Изв. АН. Сер. хим. 2016. № 1. P. 54.

Supplementary files

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2. Fig. 1. Structure of the A-benzoquinone L4 molecule (thermal ellipsoids of 30% probability are shown) a; b is a superposition of the structures of molecules A and B (green and blue bonds, respectively) of the L4 compound with thermal ellipsoids of atoms of 15% probability (hydrogen atoms are not shown).

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3. Fig. 2. Molecular structure of complexes I (a) and III (b, molecule A); superposition of structures of molecules A and B of complex III (green and blue bonds, respectively) (c). Thermal ellipsoids of 50% probability are shown. Hydrogen atoms are not shown.

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4. Fig. 3. CVA curves for complexes II and III (glassy carbon electrode, Ag/AgCl/KCl, 0.2 M [n-Bu4N]ClO4, CH2Cl2, c = 2 × 10-3 mol/l, V = 0.2 V/s, Ar).

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5. Scheme 1.

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6. Scheme 2.

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