Skip to main content
SpringerLink
Log in

Synthesis and Molecular Structure of a Chiral Bipyridine-Menthol Ether

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

Abstract

This paper presents the synthesis and structural characterization of 6,6′-bis[(1R,2S,5R)-isomenthoxy]-2,2′-bipyridine obtained by homocoupling of chiral pyridyl-ether 2-bromo-6-[(1R,2S,5R)-isomenthoxy]-pyridine. The two-step synthetic procedure afforded chiral bipyridine in a good yield and the structure of the compound is determined by X-ray diffraction. It crystallizes in a non-centrosymmetric chiral crystal structure type (P2, a = 10.7543(8) Å, b = 8.4488(6) Å, c = 15.8964(10) Å, β = 104.035(7)°, V = 1401.24(17) Å3, Z = 2). Moreover, the compound is characterized by FTIR, high resolution mass spectrometry and its complexation capacity to transition metals is studied by UV-Vis spectroscopy.

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

Access this article

Log in via an institution

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

Instant access to the full article PDF.

Institutional subscriptions

Similar content being viewed by others

References

  1. A. V. Malkov and P. Kocovsky. Curr. Org. Chem., 2003, 7, 1737–1757.

    Article  CAS  Google Scholar 

  2. H. L. Kwong, H. L. Yeung, C. T. Yeung, W. S. Lee, C. S. Lee, and L. W. Wong. Coord. Chem. Rev., 2007, 251, 2188–2222.

    Article  CAS  Google Scholar 

  3. E. Gnanamani, N. Someshwar, J. Sanjeevi, and C. R. Ramanathan. Adv. Synth. Catal., 2014, 356, 2219–2223.

    Article  CAS  Google Scholar 

  4. H. Zhao, Y. Yue, H. Li, Z. Sheng, Z. Yang, and W. Meng. Chin. J. Chem., 2013, 31, 485–493.

    Article  CAS  Google Scholar 

  5. E. Gnanamani, N. Someshwar, and C. R. Ramanathan. Adv. Synth. Catal., 2012, 354, 2101–2106.

    Article  CAS  Google Scholar 

  6. G. Chelucci and F. Soccolini. Tetrahedron: Asymmetry, 1992, 3, 1235–1238.

    Article  CAS  Google Scholar 

  7. M. E. Wright, S. A. Svejda, M. J. Jin, and M. A. Peterson. Organometallics, 1990, 9, 136–146.

    Article  CAS  Google Scholar 

  8. M. C. Burla, R. Caliandro, M. Camalli, B. Carrozzini, G. L. Cascarano, L. De Caro, C. Giacovazzo, G. Polidori, and R. Spagna. J. Appl. Crystallogr., 2005, 38, 381–388.

    Article  CAS  Google Scholar 

  9. G. Sheldrick. Acta Crystallogr., Sect. A, 2015, 71, 3–8.

    Article  Google Scholar 

  10. H. D. Flack. Acta Crystallogr., Sect. A, 1983, 39, 876–881.

    Article  Google Scholar 

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

    Article  CAS  Google Scholar 

  12. S. K. Wolff, D. J. Grimwood, J. J. McKinnon, D. Jayatilaka, and M. A. Spackman. CrystalExplorer 2.1. Perth, University of Western Australia: Perth, 2001.

    Google Scholar 

  13. I. J. Bruno, J. C. Cole, M. Kessler, J. Luo, W. D. S. Motherwell, L. H. Purkis, B. R. Smith, R. Taylor, R. I. Cooper, S. E. Harris, and A. G. Orpen. J. Chem. Inf. Comput. Sci., 2004, 44, 2133–2144.

    Article  CAS  Google Scholar 

  14. J. E. M. Lewis, R. J. Bordoli, M. Denis, C. J. Fletcher, M. Galli, E. A. Neal, E. M. Rochette, and S. M. Goldup. Chem. Sci., 2016, 7, 3154–3161.

    Article  CAS  Google Scholar 

  15. E. Fresta, G. Volpi, M. Milanesio, C. Garino, C. Barolo, and R. D. Costa. Inorg. Chem., 2018, 57, 10469–10479.

    Article  CAS  Google Scholar 

  16. M. H. Chisholm, J. C. Huffman, I. P. Rothwell, P. G. Bradley, N. Kress, and W. H. Woodruff. J. Am. Chem. Soc., 1981, 103, 4945–4947.

    Article  CAS  Google Scholar 

  17. B.-M. Ji, D.-S. Deng, W.-Z. Wang, and S.-B. Miao. J. Mol. Struct., 2009, 937, 107–115.

    Article  CAS  Google Scholar 

  18. E. C. Constable, C. E. Housecroft, V. Jullien, M. Neuburger, I. Poleschak, S. Reymann, S. Saxer, and S. Schaffner. Polyhedron, 2007, 26, 5519–5526.

    Article  CAS  Google Scholar 

  19. M. A. Spackman and D. Jayatilaka. CrystEngComm, 2009, 11, 19–32.

    Article  CAS  Google Scholar 

  20. M. A. Spackman and J. J. McKinnon. CrystEngComm, 2002, 4, 378–392.

    Article  CAS  Google Scholar 

  21. C. F. Macrae, I. J. Bruno, J. A. Chisholm, P. R. Edgington, P. McCabe, E. Pidcock, L. Rodriguez-Monge, R. Taylor, and J. van de Streek. J. Appl. Crystallogr., 2008, 41, 466–470.

    Article  CAS  Google Scholar 

  22. A. C. F. Brito, R. S. Correa, A. A. Pinto, M. J. S. Matos, J. C. Tenorio, J. G. Taylor, and T. Cazati. J. Mol. Struct., 2018, 1163, 197–204.

    Article  Google Scholar 

  23. A. Gavezzotti and G. Filippini. J. Phys. Chem., 1994, 98, 4831–4837.

    Article  CAS  Google Scholar 

  24. E. Fresta, G. Volpi, M. Milanesio, C. Garino, C. Barolo, and R. D. Costa. Inorg. Chem., 2018, 57, 10469–10479.

    Article  CAS  Google Scholar 

  25. D. L. Gerlach, S. Bhagan, A. A. Cruce, D. B. Burks, I. Nieto, H. T. Truong, S. P. Kelley, C. J. Herbst-Gervasoni, K. L. Jernigan, M. K. Bowman, S. Pan, M. Zeller, and E. T. Papish. Inorg. Chem., 2014, 53, 12689–12698.

    Article  CAS  Google Scholar 

Download references

Acknowledgments

We would like to thank the Brazilian Research Agencies: CNPq, CAPES and FAPEMIG. The authors are thankful to Dr J.C. Tenorio for X-ray diffraction facilities.

Funding

R. S. Correa would like to thank the financial support provided by CNPq (grant 403588/2016-2 and 308370/2017-1) and FAPEMIG (APQ-01674-18).

Author information

Authors and Affiliations

  1. Departamento de Química, ICEB, Universidade Federal de Ouro Preto, Campus Universitário Morro do Cruzeiro, Ouro Preto-MG, Brasil

    A. B. de Carvalho, G. M. Diogo, R. S. Correa & J. G. Taylor

Authors
  1. A. B. de Carvalho
    View author publications

    You can also search for this author in PubMed Google Scholar

  2. G. M. Diogo
    View author publications

    You can also search for this author in PubMed Google Scholar

  3. R. S. Correa
    View author publications

    You can also search for this author in PubMed Google Scholar

  4. J. G. Taylor
    View author publications

    You can also search for this author in PubMed Google Scholar

Corresponding authors

Correspondence to R. S. Correa or J. G. Taylor.

Ethics declarations

The authors declare that they have no conflict of interests.

Additional information

Additional Information

Crystallographic data were deposited with the Cambridge Crystallographic Data Centre as a supplementary publication [Compound 4: CCDC 1943232]. Copies of the data can be obtained, free of charge, on application to CCDC, 12 Union Road, Cambridge CB12 1EZ, UK [f]+44 1223 336033 or e]deposit@ccdc.cam.ac.uk]. 1H NMR (Fig. S1), 13C{1H} NMR (Fig. S2), HRMS (Fig. S3), IR (Fig. S4), crystal structure analysis (Figs. S5–S8), UV-Vis experiments (Figs. S9–S10), details of crystal refinement (Table S1) and selected bond lengths and Mogul analysis (Table S2).

Text © The Author(s), 2020, published in Zhurnal Strukturnoi Khimii, 2020, Vol. 61, No. 5, pp. 805–810.

Electronic supplementary material

Rights and permissions

Reprints and permissions

About this article

Check for updates. Verify currency and authenticity via CrossMark

Cite this article

de Carvalho, A.B., Diogo, G.M., Correa, R.S. et al. Synthesis and Molecular Structure of a Chiral Bipyridine-Menthol Ether. J Struct Chem 61, 763–768 (2020). https://doi.org/10.1134/S0022476620050121

Download citation

  • Received:

  • Revised:

  • Accepted:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1134/S0022476620050121

Keywords

Search

Navigation