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Synthesis and Molecular Structure of a Chiral Bipyridine-Menthol Ether

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.

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References

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

    CAS  Article  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.

    CAS  Article  Google Scholar 

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

    CAS  Article  Google Scholar 

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

    CAS  Article  Google Scholar 

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

    CAS  Article  Google Scholar 

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

    CAS  Article  Google Scholar 

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

    CAS  Article  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.

    CAS  Article  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.

    CAS  Article  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.

    CAS  Article  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.

    CAS  Article  Google Scholar 

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

    CAS  Article  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.

    CAS  Article  Google Scholar 

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

    CAS  Article  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.

    CAS  Article  Google Scholar 

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

    CAS  Article  Google Scholar 

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

    CAS  Article  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.

    CAS  Article  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.

    CAS  Article  Google Scholar 

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

    CAS  Article  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.

    CAS  Article  Google Scholar 

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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).

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

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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.

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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

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

Keywords

  • menthol
  • bipyridine
  • ligand
  • metal
  • crystal structure
  • synthesis