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Optically active derivatives of terephthalic acid: synthesis and crystal structures

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Abstract

New optically active derivatives of terephthalic acid, which are of interest as precursors of chiral metal-organic frameworks (MOFs), were synthesized starting from available dimethyl 2-aminoterephthalate, N-Boc-l-alanine, and N-Boc-l-proline. The crystal structures of three samples were determined by powder X-ray diffraction. In all three structures, the acid molecules exist as zwitterions.

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References

  1. Metal-Organic Framework Materials, Eds L. R. MacGillivray, C. M. Lukehart, John Wiley & Sons Ltd., Chichester, West Sussex, United Kingdom, 2014, 589 pp.

  2. The Chemistry of Metal-Organic Frameworks, Ed. S. Kaskel, Wiley-VCH Verlag Gmb H&Co. Weinheim, 2016, vol. 1, 2, 849 pp.

  3. V. I. Isaeva, L. M. Kustov, Petroleum Chemistry (Engl. Transl.), 2010, 50, 167.

    Google Scholar 

  4. M. Eddaoudi, H. Li, O. M. Yaghi, J. Am. Chem. Soc., 2000, 122, 1391.

    Article  CAS  Google Scholar 

  5. M. Eddaoudi, J. Kim, N. Rosi, D. Vodak, J. Wachter, M. O´Keeffe, O. M. Yaghi, Science, 2002, 295, 1397.

    Article  Google Scholar 

  6. J. L. C. Rowsell, O. M. Yaghi, Micropor. Mesopor. Mater., 2004, 55, 217.

    Google Scholar 

  7. M. Yoon, R. Srirambalaji, K. Kim, Chem. Rev., 2012, 112, 1196.

    Article  CAS  Google Scholar 

  8. M. Padmanaban, P. Müller, C. Lieder, K. Gedrich, R. Grünker, V. Bon, I. Senkovska, S. Baumgärtner, S. Opelt, S. Paasch, E. Brunner, F. Glorius, E. Klemm, S. Kaskel, Chem. Commun., 2011, 47, 12089.

    Article  CAS  Google Scholar 

  9. D. T. S. Rijkers, H. P. H. M. Adams, H. C. Hemker, G. I. Tesser, Tetrahedron, 1995, 51, 11235.

    Article  CAS  Google Scholar 

  10. A. R. Benoit, C. Schiaffo, C. E. Salomon, J. R. Goodell, H. Hiasa, D. M. Ferguson, Bioorg. Med. Chem. Lett., 2014, 24, 3014.

    Article  CAS  Google Scholar 

  11. Y. Song, A. D. Sercel, D. R. Johnson, N. L. Colbry, K.-L. Sun, B. D. Roth, Tetrahedron Lett., 2000, 41, 8225.

    Article  CAS  Google Scholar 

  12. Y. Ohfune, N. Kurokawa, N. Higuchi, M. Saito, M. Hashimoto, T. Tanaka, Chem. Lett., 1984, 441.

    Google Scholar 

  13. A. F. Abdel-Magid, C. A. Mayano, K. G. Carson, Tetrahedron Lett., 1990, 31, 5595.

    Article  CAS  Google Scholar 

  14. V. V. Chernyshev, Russ. Chem. Bull. (Int. Ed.), 2001, 50, 2273.

    Article  CAS  Google Scholar 

  15. W. I. F. David, K. Shankland, Acta Crystallogr. Sect. A, 2008, A64, 52.

    Article  Google Scholar 

  16. K. D. M. Harris, Top. Curr. Chem., 2012, 315, 133.

    Article  CAS  Google Scholar 

  17. A. L. Spek, Acta Crystallogr. Sect. D, 2009, D65, 148.

    Article  Google Scholar 

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

    Article  CAS  Google Scholar 

  19. V. B. Zlokazov, V. V. Chernyshev, J. Appl. Crystallogr., 1992, 25, 447.

    Article  Google Scholar 

  20. L. M. Gornostaev, Yu. G. Khalyavina, A. S. Kuznetsova, O. I. Fominykh, D. A. Tropina, E. V. Murashova, I. A. Zamilatskov, V. V. Chernyshev, Russ. J. Org. Chem. (Engl. Transl.), 2016, 52, 80.

    Article  CAS  Google Scholar 

  21. S. V. Andreev, S. A. Zverev, I. A. Zamilatskov, N. M. Kurochkina, G. V. Ponomarev, A. N. Fitch, V. V. Chernyshev, Acta Crystallogr. Sect. C, 2017, C73, 47.

    Article  Google Scholar 

  22. C. R. Groom, F. H. Allen, Angew. Chem., Int. Ed., 2014, 53, 662.

    Article  CAS  Google Scholar 

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Correspondence to V. V. Veselovsky or V. V. Chernyshev.

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Dedicated to Academician of the Russian Academy of Sciences G. A. Abakumov on the occasion of his 80th birthday.

Published in Russian in Izvestiya Akademii Nauk. Seriya Khimicheskaya, No. 9, pp. 1589—1596, September, 2017.

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Veselovsky, V.V., Lozanova, A.V., Isaeva, V.I. et al. Optically active derivatives of terephthalic acid: synthesis and crystal structures. Russ Chem Bull 66, 1589–1596 (2017). https://doi.org/10.1007/s11172-017-1928-z

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  • DOI: https://doi.org/10.1007/s11172-017-1928-z

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