Skip to main content
Log in

Molecular and Crystal Structure of 2-Amino-Polyfluorophenyl-4,4,5,5-Tetramethyl-4,5-Dihydro-1H-Imidazol- 3-Oxide-1-Oxyls

  • Published:
Journal of Structural Chemistry Aims and scope Submit manuscript

Abstract

By cross-coupling of 2-iodo-polyfluoroanilines with a [AuPPh3NN] complex (where NN is 4,4,5,5- tetramethyl-3-oxide-1-oxyl-2-imidazolin-2-ide) in the presence of [Pd(PPh3)4], nitroxide radicals (2-aminopolyfluorophenyl- 4,4,5,5-tetramethyl-4,5-dihydro-1H-imidazol-3-oxide-1-oxyls) are synthesized. Their molecular and crystal structures are determined by the X-ray crystallographic analysis. It is shown that in the solid phase there are both intra- and intermolecular hydrogen bonds between NH2 groups and O atoms of paramagnetic fragments, which link the molecules into chains or dimers.

This is a preview of subscription content, log in via an institution to check access.

Access this article

Price excludes VAT (USA)
Tax calculation will be finalised during checkout.

Instant access to the full article PDF.

Similar content being viewed by others

References

  1. Nitroxides: Applications in Chemistry, Biomedicine, and Materials Science / Eds. G. I. Likhtenshtein, J. Yamauchi, S. Nakatsuji, A. I. Smirnov and R. Tamura. Weinheim, Germany: Wiley-VCH Verlag GmbH & Co., 2008.

  2. A. Alberti. Nitroxide Radicals and Nitroxide Based High-Spin Systems. Molecules and Radicals, Landolt-Boernstein Series, vol. 26D. Berlin, Heidelberg: Springer-Verlag, 2005.

    Google Scholar 

  3. Nitroxides–theory, experiment and applications / Ed. A. I. Kokorin. Rijeka, Croatia: In Tech, 2012.

  4. Stable Radicals: Fundamentals and Applied Aspects of Odd-Electron Compounds / Ed. R. G. Hicks. Chichester. UK: John Wiley and Sons, 2010.

  5. S. Rowen. Concepts and Applied Principles of Nitroxides. NY: Research Press, 2015.

    Google Scholar 

  6. M. Baumgarten. High Spin Molecules Directed Towards Molecular Magnets. Chapter 12. In: EPR of Free Radicals in Solids II. Progress in Theoretical Chemistry and Physics, vol. 25. / Eds. A. Lund and M. Shiotani. Dordrecht: Springer, 2012.

  7. Chemical Science of p-Electron Systems / Eds. T. Akasaka, A. Osuka, S. Fukuzumi, H. Kandori and Y. Aso. Japan: Publisher Springer, 2015.

  8. Molecular magnetism / Eds. K. Itoh and M. Kinoshita. Tokyo: Kodansha & Gordon and Breach, 2000.

  9. E. V. Tretyakov and V. I. Ovcharenko. Russ. Chem. Rev., 2009, 78, 971–1012.

    Article  CAS  Google Scholar 

  10. I. Ratera and J. Veciana. Chem. Soc. Rev., 2012, 41, 303–349.

    Article  CAS  PubMed  Google Scholar 

  11. K. Inoue. Metal-Aminoxyl-Based Molecular Magnets. In: p-Electron Magnetism. Structure and Bonding, vol. 100 / Ed. J. Veciana. Berlin, Heidelberg: Springer, 2001, 61–91.

  12. E. Tretyakov, S. Tolstikov, A. Suvorova, A. Polushkin, G. Romanenko, A. Bogomyakov, S. Veber, M. Fedin, D. Stass, E. Reijerse, W. Lubitz, E. Zueva, and V. Ovcharenko. Inorg. Chem., 2012, 51, 9385–9394.

    Article  CAS  PubMed  Google Scholar 

  13. W. Kaszub, A. Marino, M. Lorenc, E. Collet, E. G. Bagryanskaya, E. V. Tretyakov, V. I. Ovcharenko, and M. V. Fedin. Angew. Chem., Intern. Ed., 2014, 53, 10636–10640.

    Article  CAS  Google Scholar 

  14. M. V. Fedin, S. L. Veber, E. G. Bagryanskaya, and V. I. Ovcharenko. Coord. Chem. Rev., 2015, 289-290, 341–356.

    Article  CAS  Google Scholar 

  15. K. Doi, T. Ishida, and T. Nogami. Chem. Lett., 2003, 32, 544/545.

    Article  CAS  Google Scholar 

  16. Patent WO 2006/82400A1.

  17. L. Politanskaya and E. Tretyakov. Synthesis, 2018, 50, 555–564.

    Article  CAS  Google Scholar 

  18. L. Yu. Safina, G. A. Selivanova, K. Yu. Koltunov, and V. D. Shteingarts. Tetrahedron Lett., 2009, 50, 5245–5247.

    Article  CAS  Google Scholar 

  19. L. V. Politanskaya, I. P. Chuikov, E. A. Kolodina, M. S. Shvartsberg, and V. D. Shteingarts. J. Fluor. Chem., 2012, 135, 97–107.

    Article  CAS  Google Scholar 

  20. R. Tanimoto, S. Suzuki, M. Kozaki, and K. Okada. Chem. Lett., 2014, 43, 678–680.

    Article  CAS  Google Scholar 

  21. G. M. Sheldrick. SHELX-97. Programs for Crystal Structure Analysis (Release 97-2). University of Göttingen, Germany, 1997.

    Google Scholar 

  22. Bruker AXS Inc. SADABS (Version 2.11). Madison, Wisconsin, USA, 2008.

  23. A. L. Spek. PLATON–A Multipurpose Crystallographic Tool (Version 10M). Utrecht University, Utrecht, The Netherlands, 2003.

    Google Scholar 

  24. A. L. Spek. J. Appl. Crystallogr., 2003, 36, 7–13.

    Article  CAS  Google Scholar 

  25. C. F. Macrae, P. R. Edgington, P. McCabe, E. Pidcock, G. P. Shields, R. Taylor, M. Towler, and J. van de Stree. J. Appl. Crystallogr., 2006, 39, 453–457.

    Article  CAS  Google Scholar 

Download references

Author information

Authors and Affiliations

Authors

Corresponding author

Correspondence to E. V. Tretyakov.

Additional information

Original Russian Text © 2018 E. V. Tretyakov, T. V. Makhneva, L. V. Politanskaya, I. Yu. Bagryanskaya, D. V. Stass.

Translated from Zhurnal Strukturnoi Khimii, Vol. 59, No. 3, pp. 712–719, March-April, 2018.

Rights and permissions

Reprints and permissions

About this article

Check for updates. Verify currency and authenticity via CrossMark

Cite this article

Tretyakov, E.V., Makhneva, T.V., Politanskaya, L.V. et al. Molecular and Crystal Structure of 2-Amino-Polyfluorophenyl-4,4,5,5-Tetramethyl-4,5-Dihydro-1H-Imidazol- 3-Oxide-1-Oxyls. J Struct Chem 59, 689–696 (2018). https://doi.org/10.1134/S0022476618030289

Download citation

  • Received:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1134/S0022476618030289

Keywords

Navigation