Synthesis, Structure, and Electrochemical Properties of Cobalt Complex Based on N-(2,5-Bis(methoxycarbonyl)phenyl)-α-diphenylphosphorylglycinate

I. F. Sakhapov; Сахапов И. Ф.; A. A. Kagilev; Кагилев А. А.; A. O. Kantyukov; Кантюков А. О.; I. K. Mikhailov; Михайлов И. К.; O. S. Sof’icheva; Софьичева О. С.; D. R. Islamov; Исламов Д. Р.; Z. N. Gafurov; Гафуров З. Н.; D. G. Yakhvarov; Яхваров Д. Г.

doi:10.31857/S0044457X23601098

Synthesis, Structure, and Electrochemical Properties of Cobalt Complex Based on N-(2,5-Bis(methoxycarbonyl)phenyl)-α-diphenylphosphorylglycinate

Authors: Sakhapov I.F.¹, Kagilev A.A.¹^,2, Kantyukov A.O.¹^,2, Mikhailov I.K.¹^,2, Sof’icheva O.S.¹, Islamov D.R.³, Gafurov Z.N.¹, Yakhvarov D.G.¹^,2
Affiliations:
1. Arbuzov Institute of Organic and Physical Chemistry, FRC Kazan Scientific Center, Russian Academy of Sciences
2. Alexander Butlerov Institute of Chemistry, Kazan Federal University
3. Laboratory for Structural Analysis of Biomacromolecules, FRC Kazan Scientific Center, Russian Academy of Sciences
Issue: Vol 68, No 9 (2023)
Pages: 1287-1292
Section: КООРДИНАЦИОННЫЕ СОЕДИНЕНИЯ
URL: https://rjsvd.com/0044-457X/article/view/666263
DOI: https://doi.org/10.31857/S0044457X23601098
EDN: https://elibrary.ru/WOIXFC
ID: 666263

Cite item

Full Text

Open Access
Restricted Access

Access granted
Restricted Access

Subscription Access

Abstract

New bis-chelate cobalt(II) complex [Co(DPG)2(DMF)2] (1), where DPG is N-(2,5-bis(methoxycarbonyl)phenyl)-α-diphenylphosphorylglycinate, has been prepared and characterized. The complex is the first example of cobalt complex containing phosphorylated derivative of α-amino acid. Octahedral coordination geometry of the cobalt complex 1 has been determined by X-ray diffraction. Electrochemical reduction of the obtained complex has been found to be irreversible two-electron process (
= –1.70 V vs Ag/AgNO3, 1 × 10–2 М in CH3CN), resulting in formation of cobalt metal adsorbed on the surface of working electrode.

Keywords

α-phosphino-α-amino acid, α-diphenylphosphorylglycinate, cobalt complex, X-ray diffraction, cyclic voltammetry

References

Kotha S., Goyal D., Chavan A.S. // J. Org. Chem. 2013. V. 78. № 24. P. 12288. https://doi.org/10.1021/jo4020722
Noisier A.F.M., Brimble M.A. // Chem. Rev. 2014. V. 114. № 18. P. 8775. https://doi.org/10.1021/cr500200x
Mondal S., Chowdhury S. // Adv. Synth. Catal. 2018. V. 360. № 10. P. 1884. https://doi.org/10.1002/adsc.201800011
Lewis J.C. // Curr. Opin. Chem. Biol. 2015. V. 25. P. 27. https://doi.org/10.1016/j.cbpa.2014.12.016
Heravi M.M., Vavsari V.F. // Adv. Heterocycl. Chem. 2015. V. 114. P. 77. https://doi.org/10.1016/bs.aihch.2015.02.002
Roy S.G., De P. // J. Appl. Polym. Sci. 2014. V. 131. № 20. P. 41084. https://doi.org/10.1002/app.41084
Зарезин Д.П., Ненайденко В.Г. // Успехи химии. 2019. Т. 88. № 3. С. 248.
Софьичева О.С., Кислицын Ю.А., Нестерова А.А., Добрынин А.Б., Яхваров Д.Г. // Электрохимия. 2020. Т. 56. № 5. С. 456.
Soficheva O.S., Nesterova A.A., Dobrynin A.B. et al. // Mendeleev Commun. 2020. V. 30. № 4. P. 516. https://doi.org/10.1016/j.mencom.2020.07.038
Lach J., Peulecke N., Kindermann M.K. et al. // Tetrahedron 2015. V. 71. № 30. P. 4933. https://doi.org/10.1016/j.tet.2015.05.101
Wardle N., Annie Bligh S., Hudson H. // Curr. Org. Chem. 2007. V. 11. № 18. P. 1635. https://doi.org/10.2174/138527207783221200
Ferreira P.M.T., Monteiro L.S. // N,N-diprotected dehydroamino acid derivatives: Versatile substrates for the synthesis of novel amino acids, in: Targets Heterocycl. Syst., 2006: pp. 152–174
Marsh R.E., Donohue J. // Adv. Protein Chem. 1967. V. 22C. P. 235. https://doi.org/10.1016/S0065-3233(08)60042-X
Peulecke N., Kindermann M.K., Köckerling M. et al. // Polyhedron. 2012. V. 41. № 1. P. 61. https://doi.org/10.1016/j.poly.2012.04.019
Peulecke N., Yakhvarov D.G., Heinicke J.W. // Eur. J. Inorg. Chem. 2019. V. 2019. № 11. P. 1507. https://doi.org/10.1002/ejic.201801130
Kagileva A.A., Kagilev A.A., Kantyukov A.O. et al. // New J. Chem. 2022. V. 46. № 36. P. 17303. https://doi.org/10.1039/d2nj02578g
Dutta A., Du Bois D.L., Roberts J.A.S. et al. // Proc. Natl. Acad. Sci. USA. 2014. V. 111. № 46. P. 16286. https://doi.org/10.1073/pnas.1416381111
Oughli A.A., Ruff A., Boralugodage N.P. et al. // Nat. Commun. 2018. V. 9. № 1. P. 1. https://doi.org/10.1038/s41467-018-03011-7
Galan B.R., Reback M.L., Jain A. et al. // Eur. J. Inorg. Chem. 2013. V. 2013. № 30. P. 5366. https://doi.org/10.1002/ejic.201300751
Priyadarshani N., Ginovska B., Bays J.T. et al. // Dalt. Trans. 2015. V. 44. № 33. P. 14854. https://doi.org/10.1039/c5dt01649e
Buhaibeh R., Filippov O.A., Bruneau-Voisine A. et al. // Angew. Chem. Int. Ed. 2019. V. 58. № 20. P. 6727. https://doi.org/10.1002/anie.201901169
Lach J., Guo C.Y., Kindermann M.K. et al. // Eur. J. Org. Chem. 2010. V. 2010. № 6. P. 1176. https://doi.org/10.1002/ejoc.200901251
Фомина О., Яхваров Д.Г., Хайнике И. et al. // Ученые записки Казанского университета 2012. Т. 154. № 3.
Sheldrick G.M. // Acta Crystallogr., Sect. A: Found. Crystallogr. 2015. V. 71. № 1. P. 3. https://doi.org/10.1107/S2053273314026370
Sheldrick G.M. // Acta Crystallogr., Sect. A: Found. Crystallogr. 2008. V. 64. № 1. P. 112. https://doi.org/10.1107/S0108767307043930
Macrae C.F., Edgington P.R., McCabe P. et al. // J. Appl. Crystallogr. 2006. V. 39. № 3. P. 453. https://doi.org/10.1107/S002188980600731X
Khusnuriyalova A.F., Petr A., Gubaidullin A.T. et al. // Electrochim. Acta 2018. V. 260. P. 324. https://doi.org/10.1016/j.electacta.2017.12.050